It is around 3:00 p.m. when Johnny—or whoever else happens to be around and between shifts—sharpens the pencils. Somehow, regardless of the day or hour, each one is perfectly pointed, sitting in a bundle of similarly clean-erasered utensils in vases on each of the tables. They are all printed with the same text: “Poindexter Coffee: Graduate Hotels.”

This precision in design is how Dominic Ruggieri, the general manager of New Haven’s newest hotel, wants it. “I kind of love the fact that [students] see it as magic.”

The Graduate brand—and the Yale brand to boot—is everywhere, from the sign on the front door proclaiming the hotel’s inclusivity to the striped plastic cups students can use for water from a beehive-shaped jug. 

To your left as you walk in is the Theo Epstein Scouting Room, a riff on the Chicago Cubs president and member of the class of ‘95, where all the books on the wall are blue and in various stages of fade. Among the miscellany, there is a Yale Class of 1935 airplane bag, a collection entitled The Romances of Alexandre Dumas, and a baseball glove so ancient it could have belonged to Epstein’s grandfather. To your right is the Stirling Library, punnily named for the building’s former owner.

In the Poindexter coffee shop in the back, the chairs are red velvet and the chandeliers sparkle. The far back room, once a ballroom and now christened the “Majestic Room,” is still tiled in its original one inch thick sheet marble.

“Nostalgia is the word I like to use for it,” Ruggieri explained.

Three o’clock is the time that Ruggieri can finally take a break from his desk and do a lap around the lobby. Then, he notices, is when the students begin to arrive in full force. But sometimes, when he stays around until the late hours, he sees a couple of Yalies “tucked in the corner at 11:00 at night, still sitting there studying.”

Only one thing is off, and given the precision of every other detail, we can only assume it is intentional. The lit marquee above the hotel’s entrance at 1151 Chapel Street still proclaims in thin white lettering exactly what the building is no longer: “Hotel Duncan.”


Mike Stern is the one who brings up Murphy’s Law—“anything that can go wrong will go wrong”—when I ask him about his latest photography gig. He was supposed to be photographing tuna casserole for a client, but the mushy food got disfigured in shipping. “I’m gonna kill Murphy,” he says with an earnest laugh.

Stern—alternatively known as Mike, Mikey, and Stern Boy—is drinking Tropicana grapefruit juice out of a cup, the plastic bottle placed astride like a can of good beer. Although I offered him the seat by the wall, he quickly slid into the other one—the seat that doesn’t face the Graduate, where he lived as a permanent resident, or “perm,” in a cheap single room for 12 years.

He calls it the “Dysfunctional Arms Hotel.”

Stern is tall, with a tuft of whitening hair; slim; and talks fast. He was born, raised, and college-educated in this city, even though his Bawston twinge might indicate otherwise. 

“When I was a kid,” he begins his yarn, “a business associate of my father gave me a Polaroid camera.” He started taking pictures. Of sports, of school events, for the yearbook. At New Haven College, now called the University of New Haven, he got his own 35mm camera. He followed his love of photography wherever it took him.

It led him to a job as a reporter at the New Haven Register. (“First of all, I couldn’t type,” and the long hours and boring city government meetings made him dread waking up.)

It led him to Beantown, perhaps where he picked up the accent, where he wrote copy for the Dunkin Donuts newsletter that went to franchises around the world. (“The marketing director calls you once a year for your review. He says, ‘We like the work you do, but… you don’t seem to wanna reach out for more work.’ He says, ‘For instance, would you [one day] like my job?’ I said no…. Two weeks later I was laid off.”) 

It led him to work at an ad agency on the city’s glitzy Newbury Street, where one day he went to supervise a shoot at a full-time photographer’s studio. (“I was saying to myself, ‘Gee, I like this!’… I came to him and I say, ‘Are you looking for an assistant?’… He says, ‘I’ll put you on as a dark room guy because my dark room guy quit.’”)

It led him to work for that photographer, who Stern learned later was a rude boss and went through employees at a rapid clip. (Nonetheless, the job only ended three years later because the boss “had an opportunity to go to New York to make the big bucks—as if he wasn’t already making the big bucks—so I was back on the streets.”)

To avoid going back to the corporate world, Stern decided to open his own photography business. At that point, he was in his early thirties, and it took a few years to get the business off the ground. He points out that it’s not a cheap vocation. Between the cost of equipment, studio space, and his own lost time, “I ended up almost homeless. I starved for eight years.”

He eventually made enough to live in an apartment at the top of Beacon Hill. “You can see the planes landing at Logan. It was gorgeous.” He can still describe in great detail the exposed brick wall, the working fireplace, and the foot-wide cedar floorboards. “When you walked in you could hear ‘em creak and give a little bit.” The front closet walls smelled like fresh forest.

But the whole time, Stern was being broken down from the inside by his OCD, which he’s suffered from since he was 12. “It’s like being in a jail without bars,” he explained. “You’re physically free, but you’re not mentally free.” 

He doesn’t feel comfortable cooking, so he would eat out every night. Sometimes he would go to the fancy places like Jimmy’s Harborside; Anthony’s Pier 4; or Top of the Hub, which boasted views from the Prudential Center’s 52-story height. He bought a red ‘59 Volvo, far out of his budget, that he maintains meticulously to this day. “Every dime that I made was pretty much spent,” he shared. In other words, it was time to go home.

After stumbling through different places in New Haven (including one halfway house so dangerous, he recalls, “There was a knife at my throat, literally”), he moved into the Duncan—he didn’t need a kitchen anyway—and started to catch up with his old friends. He made a deal with Stirling Shapiro, who managed the hotel, to pay $450 a month plus labor for a bedroom in the attic and a photography studio in the unused ballroom downstairs.

“You ever heard the saying ‘You can’t go home’?” he asks. “It’s hard. It wasn’t the same.” It took him a couple of years to feel settled again. Yale helped. “There’s no place like Yale… I’m enamored with…not necessarily the education but the architecture.” One of Stern’s biggest photography projects to date has been a photo book, Yale’s Hidden Treasures, about the University’s gargoyles.

I tell Stern I want to hear his stories from his time at the Duncan; I have all the time in the world to listen. He warns me: “You might need it.” I tell him I’m ready for everything.

“Alright,” he sighs. “Then it’s not gonna be an article; it’s gonna be an exposé. You got the good, the bad, and the ugly. Which one do you wanna hear first?” 


On September 13, 2017, Stirling Shapiro, the third generation of his family to own and operate the building, sold New Haven’s Hotel Duncan at 1151 Chapel Street to Chicago-based real estate firm AJ Capital.

The Duncan, built in 1894 and Shapiro family property since 1950, was starting to look its age. Plugging in a heating pad was cause for hazard, one family member explained, and a former resident reported that until almost the very end, the front desk was staffed by a man using a manual typewriter. 

In the Duncan’s 92 rooms, about half of the guests at any given time—usually somewhere between 39 and 45—were “perms,” to use Stern’s word, paying for rent in week-to-week installments of $200 or so, or based on special agreements with Shapiro. 

The hotel in its place now, the Graduate, is one in a chain of themed boutique hotels in college towns across the country and, soon, in the U.K.. Each one is unique. The page for the Nashville, Tennessee outpost invites guests to “challenge [their] inner Opry star at our karaoke bar.” The one for Tempe, Arizona advertises “southwest style with a desert nod”—every piece of furniture seems to be coral-striped, and sketches of state flora and fauna adorn the walls.

It seems to have found the right time to come to New Haven. Hacibey “Haci” Catalbasoglu ‘19, the former alder for the area, noted the hotel-building blitz around the city: “There is definitely a short supply of hotels, and there’s a need that I think the Graduate is helping meet.” The city, plagued by years of disinvestment and outmigration, by some accounts is experiencing a renaissance. The promise of new employers, driving the retention of younger and higher-consuming residents, is on the horizon. 

It is also, Catalbasoglu acknowledged, a time of tension.

By different accounts, the city has been experiencing an affordable housing crisis since the crash of 2008. By DataHaven’s 2019 numbers, New Haven’s average renter is “$10,000 short of affording a 2-bedroom apartment.” And although construction of shiny new apartment buildings is fast, the percentage of low-income residents is rising.

Of course, as went the Duncan, so went the perms. The several dozen low-income New Haveners living in the old building in single room occupancy units (SROs), a form of affordable housing already on the decline in the city, were forced to go from here. It was, by many accounts, the most visible and publicized case of residential displacement in the city’s recent memory, even in a market rife with displacement due to absentee landlords and decreasing affordability. Indeed, the year before the Duncan was sold, 4.05 percent of renters were evicted, the 69th highest rate in the country, but most cases slipped and continue to slip under the radar. 

“Before the Duncan [sale] and [the subsequent social movement], it wasn’t the case that every single New Haven City official was talking about affordable housing,” Ming-Yee Lin, a lawyer at the New Haven Legal Assistance Association (NHLAA), recalled. Today, it is one of the city’s most significant political issues. 

The Duncan tipped off a years-long series of debates, advocacy groups, and proposals to fix the problem. To many advocates today, the fight has only just begun.

AJ Capital gutted the place—which by all accounts was long due for an upgrade—and opened its expansive glass doors to guests on October 3, 2019.


To get to the New Haven Board of Alders main chambers, you have to walk up the cast-iron main steps in the lobby. The steps themselves might fit in a 19th-century railroad station, and look ready to be lifted up into the ceiling like an attic drop-down. At the top, and if you make a left at the atrium, you’ll find the chamber itself.

This room—with its rows of pews and labeled seats for each of the city’s 30 alders—is where the Affordable Housing Task Force first convened on June 6, 2018. The task force, facilitated by then-Ward 8 Alder Aaron Greenbarg GSAS ‘19, was made up of a group of seven community and government leaders, including the nonprofit leader Ed Mattison and Karen DuBois-Walton, a member of the task force and President of Elm City Communities, the city’s housing authority. 

DuBois-Walton widened her eyes in when I asked why the task force formed when it did—instated in March 2018, a half a year after the Duncan announcement: It seemed so obvious. But even then, everyone was a little surprised by the Duncan’s sudden importance. “Had that not happened as part of a larger context of pressures on the affordable housing market…. I don’t think the Duncan story would have been what it was,” she explained.

Indeed, Mattison explained, before the Task Force, “There was a lot of moaning and groaning but not much happening.”

The June gathering was to be the first of six meetings in City Hall, often in that same chamber, one each month until the Task Force legally disbanded in the new year. The large room was consistently full. 

A coalition of affordable housing advocacy groups, self-titled Room for All, formed to take full advantage of the new platform. Because Room for All—which included individual community members and groups like NHLAA, where Ming-Yee Lin works; Mothers and Others for Justice; and Y2Y New Haven—was made up of locals who worked on these projects full-time and filled up the pews with their own members, these groups often ended up directing the conversation instead of the task force members up front. 

But the time crunch was clear. Meetings could get “super super rushed because [the task force] was set to dissolve in [2020],” Ali Bauman ‘21, a Yale student who attended the meetings, explained. Mattison also shared that the Board of Alders—which was supposed to help staff the task force—was too busy to help much. As a result, avid Room for All members would put in extra work outside of the task force meetings to keep them as productive as possible. 

The monthly conversations were sprawling and at times unwieldy, exploring issues of housing affordability from reducing parking lot requirements to the city’s often-tense relationship with its surrounding suburbs to enabling the construction of tiny homes called accessory dwelling units. Most members assumed that the Duncan was a starting point and nothing more.

“I would say the one person that continued to carry the Duncan through the conversation was Ed Mattison,” Bauman reflected.

In fact, when asked about SROs, Mattison jumped to say, “That’s my thing!”

Mattison, who now sports a gray beard, first arrived at Yale Law School in 1964, straight from the Peace Corps in Colombia. He bought his first home soon after moving here full time, for only $33,000, in the area near Blue State Coffee on Orange. Today, the neighboring house, which looks just the same, went for $410,000 a few years ago. “Essentially all the kinds of people who lived on our block are gone,” he lamented. In fact, “The lady across the street is the only remaining one.”

After entering into semi-retirement, Mattison began working as the Coordinator of Special Projects at Continuum of Care, which, true to its name, provides a continuum of services for patients with persistent mental health issues, including substance abuse.

His “moment of fame,” as he shared with The Politic, was back in the mid 2000s when he facilitated the sale of 360 State Street, a 32-story high rise for which construction began at the peak of the American real estate bubble in 2008. It had been an undeveloped parking lot for far too long, and “it wasn’t even successful as a parking lot.” 

Mattison’s task was to broker a deal to sell the land to developers for $1. Not everyone was happy with what looked like a free lunch for the corporate types, and Mattison himself was disappointed when the promised set-aside of Section 8 units still ended up being unaffordable for many locals. 

Today, the building has faded into the urban fabric. It is perhaps best known now for the Elm City Market on its ground floor.

360 State Street is one—very tall—piece of a larger trend. Mattison calls it the “Fake Renaissance.” Cities like New York and Stamford are becoming increasingly expensive, and New Haven has become increasingly appealing following upscale development by local Joel Schiavone in the ‘80s and by Yale Vice President for New Haven and State Affairs Bruce Alexander in the ‘00s. Transit into the cities has only gotten easier and more popular for would-be commuters. One day, when Mattison was boarding the Metro-North from New Haven to Manhattan at 6:30 a.m., he was stunned that he “had the last seat.” 

With low unemployment, low interest rates, and increasing numbers of millennials moving into the city during the mid aughts, former Mayor John DeStefano explained with his characteristic good-natured frankness, there was “lots of excess capital and people started building shit all over the freaking place.”

A big part of the problem, Mattison thinks, is that New Haven hasn’t yet chosen its character. The people I talked to often commented that New Haven is not like Bridgeport, referred to synecdochically for high-poverty, high-crime Connecticut cities. But nor is it like Stamford, which from the Metro-North train looks like a series of shiny glass buildings, and is home to the corporate headquarters of the likes of vacation chain Starwood Hotels, kitchenware line Cuisinart, and salmon shorts-promoter Vineyard Vines.

As the opportunity for growth comes knocking, New Haven can dig in its heels and try to maintain its affordability, through preserving its often-dilapidated housing stock, or it can look to expand—at the peril of poorer residents. Or it can figure out a middle path. The door to the city’s future has been flung wide open; it’s unclear what comes next.

“The Duncan was the straw that broke the camel’s back,” Bauman said. The building’s 30-to-40-some-odd residents made up a tiny part of the count of people experiencing housing insecurity in the city, but their dramatic displacement was key to mobilizing public support. The Duncan is now an inextricable chapter in New Haven’s fair housing narrative.


Haci Catalbasoglu wishes he had been a history major. “History repeats itself,” the former Ward 1 alder and political science major explained. New Haven, he thinks, is no exception. The leadership of the city—whether the local government, Yale administrators, or business officials—has been a glutton for redevelopment for much of the twentieth century. 

The city was, after all, built on a foundation of experimental urban design. The Nine Square Plan, the famous 18th-century project that anchored the city around a central green and eight surrounding blocks, has become a key part of the city’s legacy. That plan, the first of its kind in colonial America, has since become a historic landmark and remains a common touchstone for New Haveners.

When Richard C. Lee was sworn into office in 1954, however, he accelerated the pace of redevelopment. A report done by Lee’s Community Improvement Program in 1965 retroactively laid out his claim to construction necessity: when he took office, “downtown was obsolete, congested, and physically and economically decayed.” A report by the New Haven Journal-Courier in 1954 confirmed that New Haven was hemorrhaging retailers and citizens by the time the new mayor took office; Lee, in a statement to the Board of Alders, implored them to work to fix “a declining business district…too much slum housing and too little new housing.”

Lee’s plan was multifaceted and far-reaching, but is perhaps best remembered for the construction of the Oak Street Redistributor, a highway running through New Haven with the intention of promoting commuter access to—and spending in—the city. 

But of course to make room, something had to go. The reported numbers vary, but according to the New Haven Redevelopment Agency records on file at Yale Manuscripts and Archives, somewhere between 650 and 881 families were displaced by the Oak Street Project. Approximately 350 businesses were forced to shutter or move. Some estimate that over 3,000 people were pushed out. 

“The Oak Street neighborhood wasn’t included in discussions of their entire neighborhood being plowed to the ground,” Catalbasoglu explained. 

New Haven earned its nickname “The Model City” under Lee’s tenure, both due to the ample federal funding used in the project and its large-scale change.

Catalbasoglu didn’t miss a beat before arguing: “A lot of the discussions we’re having today were the same discussions that they were having in the ‘50s during the reign of Dick Lee.” 


After the tenth grade, in 1970, Leah Errickson née Shapiro transferred to Richard C. Lee High School after several years too many of being bullied in school. Errickson was different from the kids there, she remembers. She had spent the first eight years of her life in the more affluent Woodbridge, CT. She wore fancy clothes. And, perhaps most tellingly, she described the school as “Named after Richard C. Lee, [who] was a friend of my dad’s.”

Errickson’s father, Harold Shapiro, was a man about town. The once-Ward 21 chairman was known for his political career and business acumen—he also owned the Duncan Hotel. 

The Shapiro family first acquired the Duncan when its patriarch, Romanian immigrant Irving Shapiro, bought the place in 1950. Harold started managing the hotel right away. It became useful for everything. The back ballroom became campaign offices for New Haven Congressman Robert Giaimo, who served from 1959-1981. What is now the Theo Epstein room was once a space for Errickson to try her hand at hairdressing. 

But the building had become useful much earlier. When Errickson was around five years old, her parents began to have marital troubles. She noticed her father staying overnight in a room in the Duncan more and more, until finally, it seemed like he lived there. When she was eight, and the divorce finalized, the whole family moved to New Haven full time.

Errickson was disappointed to leave her friends, her nice school, and her Jewish community, but soon—as eight year olds are wont to do—she moved on. “This is an adventure,” she recalled thinking.

When she wasn’t in school, Errickson would take the long walk from her new home on Winthrop Avenue to hang out downtown. Sometimes, she would spend time with her older siblings and their friends. Other times, she would go alone: “I was kind of a loner [in that way].”

She would spend a large chunk of that time at the Duncan. As a child, she had the run of the place. The elevator operator and front desk clerk would let her into any empty room she wanted. She remembers with horror the Columbus Day parades, when she’d have to dress up all nice and sit on the Duncan’s porch while her friends “snickered” from the sidewalk below. Sometimes, she would ask the operator to let her upstairs, so she could sit in her silly finery and watch from the bay windows of a suite without being seen. 

Harold would also put the kids to work. Stirling or their middle sister Dorian would man the front desk; Errickson the hand-operated elevator. There would be campaign work too. “We grew up in a fishbowl,” Errickson explained. The sisters would run voter coordination efforts for Congressman Giaimo, or Harold’s latest connection, while Stirling drove people to the polls.

At age 15, Errickson moved into room 404 full time. Her mother had started fighting with her then-boyfriend in the Winthrop Avenue house, and Harold was quick to give Errickson—and her own boyfriend at the time—separate rooms in the hotel.

Errickson to this day seems proud of her independence. “I lived in a hotel going to high school,” she said matter-of-factly. “How many kids did that? Noooone.”

She ate at the Old Heidelberg bar downstairs, where meals were basically free, and schmoozed with adult residents. She kept her cats in the attic and had to put a pillow over her head to go feed them so the bats living there wouldn’t flap at her. She cut her friends’ hair in the ballroom in the back. (One time, in fact, she was both cutting hair and fending off bats that had entered the lobby.)

She graduated from high school in ‘72, opened her hair salon in the lobby in ‘77—the decor all gold and white and baby blue, and some of the furniture poached from the items of formerly-evicted tenants that Harold and then Stirling had hoarded in the attic and ballroom—and somewhere in between moved into room 512, where, she recalls with perhaps a tinge of urban lore, Rita Moreno once stayed.

In 1980, Errickson moved out and far across the country to Mesa, Arizona, where she still lives with her daughter and husband. 

She shared that she never “really realiz[ed] just how crazy it was” growing up like that. 

When Harold died in 1987, Leah, Stirling, and Dorian each took part ownership. Stirling managed the place full time, which gave him the upper hand in decision-making when it came time for sale.


Down in the basement was the Old Heidelberg, a staple starting in 1958. Stern still remembers it well. 

It was a college joint, a comfortable mix of part-bar, part-bistro. Errickson recalls steak-for-two that could have filled four, something like a chicken Cordon Bleu, and “a huge shrimp cocktail.” Stern opted for the steaks or the burgers, but mostly he was there for the company.

“Every Thursday night was college night, and we used to go in there when I was in college and try to meet girls,” he shared. It was the place to be—for students, some nights; for Yale parents, others; for the Shapiro family, always. 

When the original Old Heidelberg was run into the ground in the mid-2000s, it was replaced by the flagship restaurant of a Thai chain spreading across the state.

Under the management of Thai Taste, however, much of the space stayed the same. It had these memorable mahogany walls and wood beams. It was too expensive (or too much work) to get rid of the long bar on the left, which was ultimately used for storage. One local Yelp reviewer described it as an Old Heidelberg fan might have remembered the former restaurant: a “kind of a dark out of the way space.” It felt old, “rustic,” Stern recalled. 

Although the food was often well reviewed, Stern, who had worked as a housekeeper at one point when staff was short, was skeeved. “Rats like this,” he recalled, demonstrating by putting his hands farther apart than one would like to believe. “Water rats…. Disgusting.” 

The “new Old Heidelberg” in the Graduate aims to harness the good while cleaning away the bad. The original tables and chairs had been preserved in the extensive basement behind Thai Taste, and all they needed was a fresh coat of shellac.

It certainly was a place to be. In the Yale Class of 1981 Facebook page, alumni prompted to think about the Old Heidelberg remembered the sign above the bar erroneously as “I.I.T.Y.W.T.M.W.Y.B.M.A.B.,” and debated over individual letters. (The real sign, which reads “I.I.T.Y.W.I.M.W.Y.B.M.A.D.”—“If I tell you what it means will you buy me a drink?”—took me and a few strangers several embarrassing minutes and too-good-to-be-true hints to figure it out before the bartender kindly told us. We, unfortunately for this story, did not buy him a drink.)

The nostalgia, as always, was the most exciting part. Ruggieri recalled that “Many times during the opening, we’d walk around [and] you’d hear somebody walk by and say ‘Oh, they’re opening the Old Heidelberg again?’…We wanted to preserve that.”

There’s still a ways to go. The cooking hood from Thai Taste remains unusable, and the restaurant’s offerings are still barely more than bar fare. Ruggieri hopes one day to bring it back to its former glory.


Errickson tells me she has been sick for 30 years. Most of the time, something hurts; some of the time, most things hurt. Nonetheless, between doctor’s visits, supporting her adult daughter, and living her own life in Mesa, she always made it back to the Duncan to visit her favorite spots.

The first thing she made time for was pizza. She and Stern “used to go [to Yorkside] a lot.” Before the bad news, they’d talk about everything and nothing, like no time had passed. Their health; the latest drama at the hotel. During his years at the Duncan, Stern ate a lot of frozen dinners that he would secretly microwave in his room. He would eat out, too, but going out with Errickson was a treat.

One time, the two were so deep into reminiscing that they decided to take a literal trip down memory lane. They slid into Stern’s ‘59 Volvo and drove to Errickson’s childhood home. “He could barely see. I thought I was going to have a heart attack,” Errickson remembered without a hint of sarcasm. She kept pointing and saying “uh, red light!” But the car was too special for him to let anyone else drive.

They went to Woodbridge, past her old synagogue, and to the house she grew up in. She showed him her old school. Before they came back to New Haven, they stopped at a bar called the Blue Check, where her mother “used to take us and we’d get these big red fireballs. It burns your mouth out. Don’t ask me why I liked it so much.”

Long before the Duncan went on the market, the Blue Check, too, was for sale. As Stern and Errickson sat at the picnic tables in the back, the owner chatted them up. Preparing for the inevitable, they talked about their memories of the bar and what would come next.

The two of them drove back to the city.

Sometimes when they would have these Yorkside lunches, Stern would get swordfish sandwiches—“[Mike] turned me on to them,” Errickson shared. “They’re fantastic. [Only] seven dollars!” Sometimes, they would get pizza. The food was great, but what they really loved was the atmosphere. “You got all the old pictures of all the Yale people [on the walls], the old blues and everything,” Stern recalled fondly.

“I love those people,” he said. “I know all the waitresses and the waiters and everything.” George, the owner, even put an advertisement for Stern’s book on gargoyles in the pizzeria’s front window.


We start with the ugly.

“You ever hear of John Hinckley?” Stern asked conspiratorially. I nodded, vaguely recalling something from history class, or maybe a CNN documentary, about the Jodi Foster stalker and would-be Reagan assassin. “Where do you think he stayed when he stalked?” 

That was before Stern moved in, but gossip in his day still spread like wildfire. He often heard it first: between working alternately as bellman, deskman, and housekeeper, and being a generally conversational guy, he got to know the guests. Stern remembered one who would come in from the Upper East Side twice a week to teach a course (Stern scoffs here) on “architectural shrubbery”; the man, he recalled, owned an island off the coast of Maine. He remembers Yale parents; fancy professors. He was always confused why those types came.

“If you want luxury, look elsewhere…and pay more,” Bob Neubauer wrote in an October 2017 review of the Duncan. The Yelp page for the closed hotel is replete with the same criticisms, over and over. Rarely was anyone there to man the hand-operated elevator. The lighting was creepily dark. The hallways smelled like nicotine and sweat.  Whoever was at the front desk was incompetent, or rude, or both. 

A Yelper named Robyn summed it up in May 2012: “this place is a SH-T HOLE!!!!! However, we kind of enjoyed our stay here. (In a weird way!)” 

That was only the beginning. True to his promise, Stern left nothing out of his description. He started off simple: “I gotta tell you: bugs, bed bugs, roaches, mice and an occasional bat.”

Theft was commonplace. Stern described “shrinkage,” the process whereby the bellmen and housekeepers would slowly steal sheets, or laundry detergent, or toilet paper, or soap. One day, while she was still living there, Errickson was out at night teaching ballroom dancing at the Fred Astaire Dance Studio that used to be on Temple Street. She returned home to find that someone had broken into her room and stolen almost everything of value.  

After she had already moved to Mesa, she came back to visit her hometown and stayed in the hotel. A guest had his expensive camera stolen. “I remember sitting with him for two hours in the lobby consoling him.” She could empathize. 

Stern likened the craziness to a Woody Allen film. Stirling’s “hair was already gray,” he said, “but if he knew…what happened in that place…it would fall out.” If Stirling had known what was going on, Stern thinks, he would have sold the building long ago.

Neubauer, who edits a magazine and was visiting New Haven for a conference run by Yale Printing and Publishing, remembered: “I took a walk down the hall and it had a sort of empty and kind of spooky feel…. It seemed a bit like old New Haven.” 

When he had to return a year and a half later for another conference, Neubauer looked to rebook at the Duncan—it was cheap, and he didn’t mind the adventure—but it was already closed. In his time between meetings, he walked up the main stairs under the awning and tried to peek in, nervous that the building was scheduled for demolition, but the windows were almost entirely covered up for construction. From what he could see, the inside was all building dust and disarray.


Errickson broke the news at Yorkside. It was the summer of 2016. 

“She says, ‘Stirling is selling,’” Stern recalls. 

Mike: Jesus, Leah, couldn’t you tell me when we weren’t eating?

Leah: Well, a lot of times I don’t see you when we’re not eating.

“I asked Stirling how much time before I get thrown out,” Stern remembered. “He hit the roof and didn’t talk to me” for a while. As Stern recalls it, Stirling, who was known to hold an impressive grudge when he wanted to, also told other guests not to talk to him. He didn’t want any of the permanent residents to get spooked. “I got along with [Stirling] great [otherwise,]” Stern added without pause. “It’s just one of those things.” Stirling did not respond to multiple requests for comment.

Eventually, though, everyone found out.

In May of 2017, Jocelyne Barsczewski of the Glendower Group, an arm of Elm City Communities, held a meeting with the permanent Duncan residents in the lobby. That meeting kicked off months of individual consultations, house tours, and furniture moving. At that first meeting, Barsczewski reported, the Glendower Group was responsible for 39 permanent residents. (The New Haven Independent put the number at 45.) 

Stern was confident from the beginning that he’d get a good deal. “I’ve got a disability, because I’ve got OCD and I was not only living there; I was working there and I had a photography studio there. If I wanted to make a stink, it would have been really hard to get rid of me because of all that’s involved.”

The Glendower Group, which has a track record for relocation projects in several Connecticut cities, though usually at the request of public housing authorities and not companies, ultimately assisted in relocating 21 of the 39 residents. Barsczewski would say nothing more about the remaining 18 other than “that was an agreement between themselves and Glendower and AJ Capital about a different type of departure.”

The process was careful and methodical. After the residents’ scheduled consults, they were taken to look at apartments and helped with application processes. Barsczewski expressed confidence that Duncan residents are better off now. The only one who left the New Haven area did so by choice to move near family. The five who opted to stay downtown were able to. Everyone was moved into a studio or a one bedroom. 

According to data provided by the Glendower Group, average monthly rent actually went down by eight percent; if you don’t count the one person who wasn’t paying rent at all to begin with, average rents went down by 13 percent. According to Barsczewski, several residents’ rents dropped almost $400. Mattison said that given the task at hand, the Glendower Group “did great.”

Barsczewski called the overall outcome a “blessing in disguise.”

Not everyone on the Board of Alders was so confident. As residents were being moved out, then-Ward 1 alder Sarah Eidelson ‘12 proposed a six-month moratorium on the demolition of SRO units. In short: although almost all residents were already displaced, the moratorium would prevent AJ Capital Partners from moving any further. 

The hesitation to remove these units makes sense. Mattison explained that since the 1950s, SROs have been few and far between. “Mayor Lee, for reasons one can [only] guess, hated rooming houses,” he shared. “We had better than 1,000 units in the 1920 census. We have 70 [legal units] now.” Mattison explained that due to Lee-era restrictions, illegal—and less regulated—single rooms sprang up; he guesses their number around 400-500.

Nonetheless, by April 17, 2018, the SRO moratorium floundered. The city placed its hopes instead in the Affordable Housing Task Force. 


Somewhere in the middle of this process, Stern gets a call. “Are you the Mr. Stern that lived in the Duncan?” he recalls a man on the other end asking. “Are you the guy that wrote that book about the [gargoyles]?” Stern confirmed and the man said, “So you’re the infamous Stern Boy. Come in, I wanna speak to you.” 

The man was Marc Wallman, a partner at Brenner, Saltzman and Wallman, which Stern describes as a “hotsy totsy law firm on Whitney Avenue.” AJ Capital had hired the firm to represent them on issues in New Haven. “We need your help,” Wallman said.

It was early 2019, and it was a cold walk to Wallman’s office on Whitney Avenue and Humphrey Street. In his only suit, Stern took a moment and marveled at the building—“one of those old brick mansions that’s been all fixed up.” At this point, Stern had until April 1 before it was time to move out.

He wrote a letter to the mayor at their behest, praising the work of AJ Capital and the Glendower Group. He spoke at City Hall. He spoke before the Board of Alders. Before each event, he donned the same suit and was given instructions at the Whitney Avenue office. In newspaper reports of his public appearances, Stern is optimistic and forgiving. An October 2017 article from the New Haven Register quotes him as saying “I just hope [New Haven] continues to grow and prosper.”

In the meantime, he was looking for a new home.

After several house tours with Barsczewski and increasing worry (He recalls telling her after seeing a particularly nice place, “I’m living hand-to-mouth on my money like a schmuck. I didn’t save any money when I was in Boston.”), Stern moved into a new apartment—a one bedroom on George Street near the corner of Dwight. AJ Capital agreed to pay his rent for a year. After two letters and two appearances in front of City Hall voicing his support for them, Stern reports, the company gave him six extra months of rent. He didn’t do it for the rent, though; he thought they were nice guys.

Stern always knew he had a good deal, but living outside of the Duncan felt different. Before, he had “free telephone, free cable, free tv, free internet. Everything free. [Even] free toilet paper.” At his new place, with its hardwood floors, beam ceiling, and brick wall reminiscent of his Boston pad, utilities alone could cost up to $500 a month out of pocket in the winter.

Stern has a tendency to look beyond himself in his appraisal of the Duncan. He missed the free utilities, but he didn’t miss the infestations, the impropriety, and the rest of the mismanagement that colored his previous life. That’s “one of the things [I said] when I testified at City Hall,” Stern recalled. “As far as I’m concerned, the city is much better off with the Duncan gone.”


On January 21, 2019, the Affordable Housing Task Force released its report, which detailed 44 different strategies to promote housing accessibility. “Everyone realized pretty quickly that there wasn’t just one thing that was going to fix the affordable housing crisis and we were going to need to come up with a massive number of recommendations,” Bauman said. Each suggestion alone would likely just be a “drop in the bucket.”

Indeed, SROs barely appear in the document, and only comes up most substantially in the conclusions: “The SRO inventory was and continues to be negligible at best and developing such housing is an expensive task.”

Over coffee at Claire’s Corner Copia, where he jokes that he holds informal office hours, John DeStefano, mayor of New Haven from 1994 to 2014, loosely outlined three key structural problems, which appeared again and again in conversation.

First, there is the problem of absentee ownership and dilapidation of units.

Mattison, for one, expressed concerns about shell LLCs buying up and flipping land. They “collect what they can” from renters without trying to maintain fair living conditions, and will eventually “make a killing” when it comes time to sell. 

Some units are degraded because of inability rather than negligence. Mark Abraham, the Executive Director of New Haven-based research nonprofit DataHaven, argued in an interview with The Politic that although housing stock quality was not directly related to the issue of affordability, many owner-occupier landlords in multi-family homes simply can’t afford to pay for necessary upgrades. 

Second, there is the problem of zoning. 

The city has tossed around several ideas, including reducing the parking requirement for new construction—a subject at issue, in fact, in the Duncan Redevelopment—and the increasingly-popular inclusionary zoning, which would require developers to reserve a certain number of affordable units in their buildings or pay into a general pot that would go to promoting affordability. 

The issue is a messy one, not least because affordability is calculated based on Area Median Income (AMI), which includes the suburbs—that raise the numbers and skew the results. It becomes a question, according to Bauman, of “affordable for who?”

Inclusionary zoning was a “sticky point,” she explained, because some task force members were worried about making the city “much less attractive to developers.” Nonetheless, inclusionary zoning seems promising. The task force proposed further studies to evaluate its feasibility. 

Current Ward 1 alder Eli Sabin ‘22 thinks revamping the zoning code is the way to go. “If we had laws that said you can only build cars that go 250 miles an hour, cars would be more expensive, and so that would mean that we would be cutting off a lot of working and middle class families from buying cars. That’s basically what a lot of our municipal zoning regulations do [across the United States]. They cut off working and middle class families from buying or being able to buy or rent affordable housing, because we don’t allow small units to be built in an affordable way.”

Third, there is the problem of the suburbs.

DuBois-Walton describes New Haven as “the anchor city” in the region: other neighboring suburbs rely on New Haven to provide a slew of social services, which keeps their populations more affluent and brings more need to downtown. To boot, suburbs don’t pitch in, making services worse for those who need them. 

She argues that “New Haven has an obligation to demand and call on the region and the state to make an investment in the communities that have suffered over the years.”

DeStefano explained further that the city needs room to expand: “We’ve been fully built out since before the Second World War. There is no vacant land.”

But Mattison maintains, and many agree, that SROs serve a unique role. “There are a great many people with a history of mental illness,” he explains, “that could manage a room but could not manage an apartment.” 

“Let me tell you something, Kaley,” Stern said as he leaned closer over his Tropicana. “Normally-adjusted people do not live in a room in a broken down hotel.”

Current Mayor Justin Elicker will not rule out SROs—he sees their role on the continuum—but he also won’t hang his hat on them. His administration is looking into a cornucopia of proposals, including inclusionary zoning, the formation of a statewide affordable housing fund, and rezoning to allow tiny houses. “There’s no one solution that’s going to address this problem,” he said in an interview with The Politic.

On April 1, 2019, the Board of Alders voted to implement the Task Force’s recommendations.


The theme for the party was an obvious choice. Thin-crust, zesty pizza is baked into the city’s history. “The reason it’s so good in New Haven is this tradition of family recipes really being repeated,” Colin Caplan explained. He wasn’t surprised, then, when the Graduate’s media team reached out to him to help them hold an opening Apizza Bash on October 23.  

“There’s no real way to describe” what he does. His best guess over the phone was either “pizza guru” or “pizza aficionado.” He teaches a class in Connecticut history at Wesleyan; has helped produce pizza themed content including movies, podcasts, and online articles; and runs the food tour company Taste of New Haven.

The afternoon started off with a 20-some-odd-person bus tour to the “Holy Trinity” of restaurants: Sally’s, Pepe’s, and Modern.

After the tour, several hundred people crowded into the hotel for pizza, and many migrated to the former ballroom to listen to experts present on the history of the food. Caplan gave his spiel—about the city’s Italian heritage, the local culture. He reminds me not to mispronounce “Apizza” (it’s “ah-beets”).

The Chicago-based AJ Capital influence, though, is still clear. To pair with Colin, they invited Windy City food writer Steve Dolinsky to talk about all things deep-dish, stuffed, and tavern-style. 

“These guys are from Chicago,” Catalbasoglu reminds us. There was an inevitable “disconnect between them and the rest of New Haven from day one”—one that has much less to do with pizza than it does with the tectonic shifts occurring beneath the surface of the local housing market.

They are trying. Ruggieri told me that he and associates are “constantly talking to the community, constantly talking to the neighbors,” and asking what they want. Part of that will take the form of staff going out into the city and volunteering, but the possibilities are still open. “A large percentage of our associates are from the New Haven community,” Ruggieri explained. “So we’re going to rely on them to guide us…to what they want to work towards.” Ruggieri himself has been working in the hotel business in Connecticut for about 10 years.

The pizza went fast. Dolinsky remembers boxes piled high on every solid surface in sight. The event was so popular that Ruggieri shared, “We had to go out for a second run.” 

As he settles in, he has big plans for the future. He wants to host more events; invite more people in. He parroted a phrase used by all Graduate brand hotels: “We like to say that we’re the living room for the community.” 

The next goal, he says, is a springtime study break event. Maybe mimosas.  

Stern has not been inside the new location at 1151 Chapel Street. “It might as well be any hotel in New York or Boston.”


“If you stay in a Hilton or a Marriott, you could be anywhere,” Susan Hughson ‘86 explained over the phone. But at the Graduate, where she stayed with her son and husband in October of 2019, “It felt like we were in an actual place.”

When Hughson had first booked, the Graduate wasn’t even open yet. But everywhere else was full, and she needed a place to stay for her son’s college tour. “It surpassed my expectations,” she shared. It was “The kind of place that if we were there longer, or if it were snowing or something, you’d imagine meeting friends in the lobby and hanging out there.”

Today, the building has none of its original shabbiness; or if it does, it’s intentional. Everything is perfect, down to drinks like the Boola Boola, the Saybrook Strip, and the Ward 1 at the bar—they consulted with Catalbasoglu on the last drink, which he shares “was pretty cool.” 

Renee Baldo, a Guilford resident and small business owner, stood at the Poindexter Coffee counter, biding time waiting for a friend and admiring the pastry selection. She remembers the “danish pastries…not cluttered on top of each other…scones, chocolate chip cookies,” and the shiny espresso machine. Johnny was behind the counter and, when Renee’s friend arrived, offered to give them both a tour. They come to New Haven often for dinner or a night out and were excited by the new place. Johnny’s “obviously a local,” Renee shared. “He knew the history of the building…. When I meet people like that that are excited about what they’re doing, it makes me excited.”

All of these touches come through in the space itself.

The sofa in the women’s bathroom (“Sofa in the bathroom?” you say. “Yes, sofa in the bathroom,” I say.) looks like a faded pink velvet croissant. The old phone booths in the lobby only call direct to the three corners of the pizza trifecta: Sally’s, Pepe’s, and Modern. Dominic learned how to operate the formerly often-inoperative manual elevator—the oldest elevator in Connecticut—and still practices with guests to stick the landing.

The Graduate, Poindexter Coffee, and the new Old Heidelberg have mostly been a visitor hit. Caplan described it as “the feeling of being in a place that’s got a past.”


After the sale of the Duncan, the first thing Errickson did was to buy a house for herself. It’s not bigger than the mobile home—“the metal box,” as she called it—she had been living in for the past 14 years, but it feels like something. The second thing she did was to buy a house for her daughter. 

She calls the months leading up to the sale “the horrible time.” She and Stirling and Dorian would argue regularly, each hoping for their fair due, all while she served as the go-between for the two older siblings who hadn’t gotten along in years. When at the eleventh hour, Dorian decided she wanted good pictures of the lobby before the sale went through, Errickson was livid. She had already put down a down payment on her house, which she couldn’t afford without the sale.

“I was furious. I was so mad, I was having a screaming fit—and I mean screaming. I was just walking around the house crying and screaming like someone had just cut off my right arm,” she recalled.

In the end, she got what she considers a pretty good deal. The three siblings split the $8 million sale evenly between them, according to Errickson, and she gets a free stay at the hotel whenever she wants—so long as she gives sufficient advance notice, rooms are available, and it’s not a busy season for Yale families, which basically leaves her the months of June and July. She doesn’t mind. Arizona summers get too hot for her liking, so the summer months are a perfect time to get away.

Errickson loved the Graduate when she visited. In her lilty voice, she told me, “Aw, they did a great job.” She just recommended stocking up on vacuum cleaners. The staff is still young compared to when she was there, and they’re figuring out the nuts and bolts. Like her, or Stirling, or her father Irving, “When you’re in the business a long time you just know stuff.” She’s proud of how hard they’re working.

The only thing she minded was the downstairs. When she went to the Old Heidelberg, expecting the Shapiro-run restaurant, she was shocked. “They opened serving up a pretzel and a sausage on a bun. Really? Most Jewish people don’t even eat pork! What a disaster!”

Although the sale has been a big help, her neighbors in Mesa haven’t made it all easy. “Now everybody thinks we’re rich,” she explained. People expect her to pay for everything. But she’s still on “a very fixed income.” 

She is still wracked with guilt, and, as she says, so is Stirling. The Duncan’s former manager, who has always led a private life, is working on his resume again. Although, according to Errickson, the Graduate kept him on to oversee the hotel for a stretch, his prospects now aren’t easy. “He doesn’t have a lot of confidence,” she explained. “He had to learn how to work a computer and he’s still struggling, even with a phone. Who’s going to hire him? Everything’s computer nowadays.” 

What hurts most is Stern. “I feel guilty because people like Mikey—he’s almost homeless.” She listed the people the Duncan closure has hurt like she has done it before. She screwed up this; she screwed up that. “I screwed up Mikey’s life. Mikey was very happy living at the hotel and walking everywhere. Now he doesn’t feel as safe where he lives.”

Indeed, when Stern walked out of the coffee shop after our meeting, he muttered something about being nervous for his walk home, through a less populated part of the city. He slapped me on the shoulder and said something like, “Be careful out there.” 

At the end of February, Stern’s rent payments from AJ Capital ran out. He got a three-month stopgap extension on his lease when, just weeks before his move-in date, he was denied tenancy at the Seabury public housing complex for not having a voucher. A pro bono lawyer at the VA is now working to get him a place there.

Eventually, he hopes to move to Seabury, which he describes as across the street from Brick Oven Pizza. He’s worried that in the transition period, he may have to move his things into storage and live in a rooming house. “But [before all of the bureaucratic complications began,] I got a nice place [at Seabury]. I can put my [photography] studio and everything in there. Not the kinda place I’d like to live, but no choice.”

For a short time, Errickson had considered putting her earnings from the hotel back in New Haven. “I actually looked at some real estate and I said [wouldn’t it] be great for me to buy [a multifamily home]…in New Haven. And keep the rents affordable.”

But between supporting herself and her daughter, and paying for increasingly costly medical bills, it didn’t seem to make much sense.


As is the case in local governments across the country, voting to implement a policy does not, at a snap of the fingers, make it appear. In the intervening months since the alders’ vote of support over a year ago, the members of the Room for All coalition have been growing impatient.

In the months leading up to September, and then November, of 2019, the city was mired in a contentious election between two Democrats that played out in both the primary and the general. For many, Lin of NHLAA explained, the election was a referendum on this very issue, and the winner’s success in large part came from his focus on affordable housing. In a 2019 interview with The Politic, Mayor Elicker explained that “housing and development rarely came up in [the] 2013 [mayoral election], whereas in 2019 every other voter mentioned it.”

Activists were willing to put the specifics of the Task Force proposals on hold until the votes came in. Elicker, after all, campaigned on a platform of maintaining affordability even as the city grows. 

But mayoral transitions get busy and things fall through the cracks.

The very first of the Task Force’s recommendations, on page one of their proposal, demands the creation of an Affordable Housing Commission. Although conversations about the commission have ebbed and waned over the past year, and debates over the makeup of its membership have surfaced and fallen, it is still unclear to activists whether it will ever happen. 

They feel they’ve been left in the dark. “We all should understand what the timeline for the commission is going to be,” Lin’s colleague Kerry Ellington, a community organizer at NHLAA, said. “We all should understand what the city is doing to work towards affordable housing, while it’s doing what it’s doing, which is allowing for the massive development of market-rate housing.”

Until the commission is there to oversee the city’s actions, Ellington explained, “we have no [governing] body to continue to push the recommendations.” 

Lin, of NHLAA, explained that the department tasked with bringing the commission to bear—the Livable Cities Initiative (LCI), run by Affordable Housing Task Force member Serena Neal-Sanjuro—has every incentive to slow the process. LCI, already overworked and understaffed, is expected to not only inspect existing housing stock, but also to prevent further displacement. 

“They’ve essentially been told that they’re responsible for [fixing] the entire affordable housing crisis,” Lin explained. Neal-Sanjuro did not respond to multiple requests for comment.

It’s a catch-22. Certainly, creating the commission could take needed time and energy from other LCI projects and the extra oversight of the commission could slow down existing processes. But without the commission, it is unclear how all of the work put in since 2017 to make sure that displacement like that at the Duncan doesn’t happen again can ever come to fruition.

According to Ellington, discussion after discussion is happening while the problem persists and lives are uprooted. “When we talk about displacement, we often get asked to prove it….People are being displaced left and right and we don’t hear those voices.”

The displacement from the Duncan may have been the loudest, but it is far from the only.


Johnny, or “Coffee Johnny” as he is better known in TripAdvisor reviews, tells me that I should not drink cold water first thing in the morning. “It’s a shock to your insides,” he explains. 

He is tall, so tall that he looks haloed in the overheard chandeliers of Poindexter Coffee in the back of the hotel’s lobby. He is slim and energetic, in a way that belies his age of “fifty….” He trails off laughing rather than specifying the exact number.

His own age excluded, Johnny seems ready to tell every story about New Haven. Before he became “Coffee Johnny,” he worked in maintenance—“not for me, but for my kids,” he clarifies—and jumped at the chance to leave his job and work instead at the valet stand at Yale New Haven Hospital. Ruggieri doesn’t hesitate to tell me that Johnny had great reviews on Tripadvisor at the hospital too. Johnny was born and raised here, a native son of The Hill.

He remembers the mall downtown, which Errickson used to visit for treats when she was young, and all the “mom and pop shops.” Today, he laments, there are only “boutique” sandwich shops left. Except for mainstay Vito’s Deli, of course, he hastily reminds me.

He took to working at the Graduate right away. “It’s of my era,” he says about the building. “It’s dated like me.”

Errickson misses the old days, when children could roam through downtown unattended; parades littered the streets; and everyone knew everyone, or at least could trace anyone within only a few degrees of connection.

New Haven has changed, and so has the Duncan, and the lives of everyone associated. “As crazy as it is,” Stern confided, “I sort of miss the place.”

Today, on the corner of York and Chapel, a standing street sign points lost travelers to key landmarks. Broadway Shopping District. Yale Payne Whitney Gym. Grove Street Cemetery. Hotel Duncan. The story of the Duncan has sprawled across the Model City, inserting itself in everyday questions of equity, affordability, and growth. Although 1151 Chapel Street faded into the urban landscape while it was there—residents could walk right by it without second thought—the place it has left behind has difficulty forgetting it. What remains to be seen is where the city will go from here.

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