Master of the City

Co-written by Jacob Wolf-Sorokin

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John DeStefano Jr. took over as mayor of New Haven in January 1994, assuming the helm of a city overwhelmed by economic woes and soaring crime rates. Blighted proper­ties dotted the city like pox on skin. Escalating violence had spilled over from the dilapidated buildings on the edge of town into the downtown district. The Yale campus was hardly immune. In the late 1980s, more than 1,000 major crimes were committed annually at Yale. Major crimes, includ­ing cases of larceny, rape, and theft, peaked in 1990 with 1,439 such reports.

Few expected DeStefano, the 49th mayor of New Haven, to last so long in this atmosphere of chaos. In New York City, where crime rates and economic despair were more pro­nounced than in New Haven, voters dispensed with Mayor David Dinkins after one term. Dinkins, who failed to suppress the Crown Heights riots in August 1991, was seen as weak and ineffectual. “Dave, Do Something!” screamed a New York Post headline. On the very day of DeStefano’s vic­tory, Dinkins was defeated in 1993 by a swaggering Republican prosecutor, Rudolph Giuliani.

As DeStefano, the longest serv­ing mayor of New Haven, prepares to pack up his corner office on the second floor of City Hall, parallels to Giuliani are apparent. Just as the tough-love practitioner transformed New York City, especially its well-heeled districts, so too DeStefano improved the Elm City. The city is undeniably a safer place in which to live, work, and study. In 2012 alone, the city welcomed 53 new businesses, a jump from 38 the previous year.

Yet, the contenders to replace DeStefano in this year’s mayoral race will not be short of ammunition with which to attack the outgoing mayor. New Haven remains one of the most dangerous cities in America. In 1995, DeStefano launched the 15-year, $1.5 billion School Construction Program, which aimed to replace or renovate every New Haven public school. The project endures, but for all the ribbon-cutting ceremonies, school performance remains lackluster. Thirty percent of students do not graduate high school. Economic development, meanwhile, has delivered uneven returns. The resurgence of downtown has brought few gains to Dixwell and Newhallville, neighborhoods with large minority populations beset by high unemploy­ment. Up to 25 percent of residents in these neighborhoods are unemployed — three times the national average.

As the debate over John DeSte­fano’s record as mayor drags on in the months leading up to the November elections, supporters and detractors agree on at least one point: DeStefano is a gifted politician. How else could this man have remained in power for as long as he has?


1Successful politicians win elec­tions by appealing to their base. Presi­dent Barack Obama’s base of women, minorities, and young voters propelled him to victory in both 2008 and 2012. For the Obama campaign, which faced a still-miserable economy, demograph­ics was destiny. The strategy was designed to take advantage of the Republican Party’s aging and narrow­ing voting base.

Electoral bases need not be as diverse as Obama’s coalition. Often, political support falls neatly into ethnic categories. In John F. Ken­nedy’s first run for Congress in 1946, the young war hero faced off against Joseph Russo, Michael Neville, and several others in a Democratic primary campaign in Charleston, Boston. In the predominantly working-class district, Irish Americans and Italian Ameri­cans voted for kin. Joseph Kennedy, the father of the 28-year-old Kennedy, allegedly paid a local janitor — also named Joseph Russo — to enter the race and siphon off votes from the “other” Russo. This confused voters and split the Italian-American vote, helping to secure the Democratic primary for Jack, who went on to win the general election by a landslide. Even the aunt of the politician Russo voted for his janitor doppelganger.

The Italian-American commu­nity has enjoyed preeminence in New Haven politics for decades. According to the 2000 census, Italian Americans comprised New Haven County’s largest ethnic group. Of the five mayors since Richard Lee’s long tenure ended in 1970, three have been Italian American. U.S. Rep. Rosa DeLauro has represented the New Haven area since 1991. The colorful Joel Schiavone emerged in the 1990s as one of the largest developers in the city, largely responsible for rehabilitating the buildings on Chapel Street. Angelo Bartlett “Bart” Giamatti served as president of Yale from 1978 to 1986.

DeStefano’s father, a police officer, walked the beat with Biaogi “Ben” DiLieto, former mayor of the city in the 1980s, when the two were on the force together. DeStefano served as a high-level aide for DiLieto. The city helped two private developers, the Fusco Corporation and Schiavone, renovate and reopen Shubert Theater and other nearby buildings to jumpstart the area downtown.

DeStefano’s close relationship with the Fusco family reflects the close-knit Italian-American connections that have defined New Haven politics for so long. In 2000, DeStefano appointed a committee to select a contractor to develop Long Wharf, the city’s waterfront district. The committee unanimously picked New England Development Corp., a nationally known Massachusetts firm that specializes in mall development. But according to the Hartford Courant, before the committee announced its decision publicly, DeStefano offered his own suggestion: Fusco Corporation.

The Fuscos’ qualifications for the job were dubious. The family business had never landed such a lucrative and ambitious gig. A string of recent fumbles, including a $118 million unpaid mortgage owed to the state and a lawsuit pending over management of another property, raised concerns. The company also said it would need a hefty public subsidy to complete the project. Nevertheless, the selection committee sided with DeStefano, sparking allegations of favoritism.

“No question, [the Fuscos] bought that deal,” Anthony Dawson, a longtime New Haven alderman who later ran against DeStefano for mayor in 2011, told the Courant staff writer, Janice D’Arcy.

A network of politicians, officials, university administrators, and powerful developers, largely from the Italian- American community, was the foundation for DeStefano’s rise to power. But the preeminence of Italian Americans in New Haven politics is waning. Much of the population has migrated to the suburbs; the city is now only 10.5 percent Italian American. New ethnic groups, especially those from Puerto Rico and Latin America, have grown steadily in numbers; of New Haven’s 130,000 residents, 27.4 percent are of Hispanic or Latino origin. Add an additional 35.4 percent representing the African-American population, and the ethnic electoral map crystallizes. As these groups have grown in numbers and political influence, DeStefano’s own community and source of strength has diminished.

In 2005, DeStefano supported a challenger’s bid to unseat Jorge Perez, a Latino alderman, as president of the Board of Aldermen. DeStefano’s camp won the battle (although Perez was later reelected), delivering the board presidency to Carl Goldfield. A number of Latino politicians campaigned the next year against DeStefano as he sought the governor’s mansion. DeStefano’s defeat was due, in part, to his lack of Latino support.

Ever the master politician, DeStefano reinvented himself, combining progressive policies with smart politics to court leaders and woo voters from this key demographic. He scored big political points by introducing the Elm City Resident Card, designed to protect the 10,000 to 15,000 undocumented immigrants in the city. Left-leaning proponents of immigration reform from around the country heralded the program. When DeStefano ran for reelection in 2011, Latino leaders like Tomás Reyes, former president of the Board of Aldermen, state Rep. Juan Candelaria, Fair Haven Alderman Migdalia Castro, and Fair Haven Alderman Ernest Santiago stood by his side. Candelaria, who campaigned against the mayor during his gubernatorial bid, cited the mayor’s more proactive approach to school reform in explaining his change of heart. Castro applauded the Elm City ID card and the mayor’s support of the statewide DREAM Act to give the children of illegal immigrants access to in-state tuition rates.

2The mayor and his economic development team have also funneled millions of dollars into Fair Haven, a Hispanic neighborhood traditionally plagued by persistent crime, poverty, and drug problems. Fair Haven has benefited from the redevelopment of vacant land and buildings, the development of a waterfront park, and the improvement of the public infrastructure. These developments have helped make the DeStefano-Latino relationship “exemplary,” Westville Alderman Sergio Rodriguez told The Politic.

DeStefano has also allied himself with powerful players within the black community, notably with the controversial pastor Boise Kimber. The alliance began back in 1989 when DeStefano first ran for mayor. Most of the black community was united against him. Voters in usually low-turnout wards waited for hours to cast a vote in order to elect John Daniels, who was hoping to become New Haven’s first black mayor. Rev. Kimber manned a lonely campaign outpost for DeStefano in Newhallville. It was based at his spiritual home, the First Cavalry Baptist Church.

Kimber helped round up votes again for DeStefano in 1993, this time with greater success. And in 2001, when DeStefano faced a tough challenge from state Sen. Martin Looney, Kimber worked hard to pull the crucial black vote and keep him in office.

DeStefano has returned the favor many times over. The mayor testified on Kimber’s behalf in court after the latter was convicted of stealing an elderly woman’s funeral money. According to a Dec. 18, 2009, article from the New Haven Independent, DeStefano gave a Kimber-run group federal money to build homes in Newhallville. The money included open-ended $30,000 annual payments to Kimber for unspecified “consultant” services; no detailed supporting paperwork was submitted.

A year after DeStefano’s 2001 reelection, the mayor appointed Kimber the chairman of the city’s Board of Fire Commissioners. Within a year, Kimber had to step down after he angered firefighters by telling them that people with “too many vowels” in their names might not be hired by the department – an obvious reference to the Italian-American community. No longer the board’s chairman, he stayed on as one of the commissioners, and in that capacity, received wide media attention in connection with the 2009 Supreme Court case Ricci v. DeStefano. That suit involved 20 New Haven firefighters, 19 of them white and two of them Hispanic, who had passed the test for promotions to management. New Haven officials invalidated the test results because none of the black firefighters who passed the exam scored high enough to be considered for the positions. The complainants — the white and Hispanic firefighters — claimed they had been denied the promotions because of their race. The court found in their favor.

Of Kimber’s involvement in the Ricci suit, New York Times columnist Ross Douthat, a conservative, wrote: “In the backroom dealing … the original decision to deny promotions to white firefighters was heavily influenced by a local African-American ‘kingmaker’ with a direct line to New Haven’s mayor.”

Yet despite Kimber’s obvious influence, his support was certainly not enough to secure the entire African-American community. Indeed, black New Havenites are too politically fragmented to operate successfully as a predictable bloc of voters, a reality that has benefited DeStefano.

“The black community fights too much amongst itself,” a member of the Democratic Town Committee, the executive body of New Haven’s Democratic Party, told The Politic. The DTC member asked to remain unnamed to avoid any political repercussions. “Take, for example, Varrick Church and Beulah Church on Dixwell Avenue,” the member said. “Both are politically active. Varrick is establishing a charter school to serve the Dixwell and Newhallville communities. But the churches just don’t get along.”

Screen Shot 2013-04-24 at 2.13.35 PMThe DTC member continued: “There are two black candidates running or considering to run for mayor this year: Gary Holder-Winfield and Kermit Carolina. Many folks within the black community believe that this mirrors the divisions within our community that undermine our strength.”

The New Haven African-American community’s inability to unite and attack has saved DeStefano more than once, most recently during the 2011 mayoral race. In a four-way Democratic primary that included two African- Americans, the incumbent finished with a plurality of just 43 percent of the vote. With an opposition divided, DeStefano triumphed.


The biggest news story from the 2011 elections, however, wasn’t DeStefano’s tenth mayoral victory. According to many city insiders, the real winners were the Yale University employees’ unions. Local 34, Yale’s pink-collar union, and Local 35, its blue-collar union, had accused the DeStefano administration of stifling democracy and paying too little attention to average taxpayers and workers. They pushed for new voices in city government.

On Sept. 13, the night of the Democratic primary, the unions captured 14 out of 15 races in which their aldermanic candidates faced City Hall-backed contenders. A few months later, in March 2012, the unions delivered once again, winning races for ward co-chairs in Dwight, Fair Haven Heights, Dixwell, Newhallville, and East Rock.

DeStefano, the master politician, didn’t skip a beat. Rather than fight the evident shift in his city’s political sentiments, he incorporated the union platform into his own. In his State of the City address in early 2012, DeStefano announced his support for a “jobs pipeline,” an idea first proposed by the Board of Aldermen only a month earlier. The pipeline, which has not yet fully formed, will comprise a set of coordinated programs that train and link job-seekers with employers.

Moreover, DeStefano didn’t wait until after his inauguration to make his first move. The unions had campaigned to bring back “community beat” policing, the practice famously caricatured by Officer Krupke in “West Side Story” musical, whereby police get out of their cars and walk the streets. DeStefano got there first. A mere month after the union’s electoral victories, the mayor appointed Dean Esserman — former chief of police for Providence, R.I., Stamford, Conn., and the New York Metropolitan Transportation Authority’s Metro-North Police Department — as the New Haven Police Department’s new chief. One of the changes Esserman implemented within the Police Department was to resuscitate this abandoned practice. In the face of new and harsher political realities, only three years after denouncing the old-style community policing approach, DeStefano reversed course.

Rob Smuts ’01, the city’s chief administrative officer, is confident of the strength of the relationship forged between the union-backed aldermen and the mayor. “We have to have a good working relationship with the Board of Aldermen,” he told The Politic. But it hasn’t been easy. “There are 30 part-time alderman, each of whom has a day job. We have to do a lot of work to make sure they all feel included.”

Bruce Alexander, Yale’s vice president for New Haven and state affairs, echoed Smuts’ sentiments to The Politic. The city has seen progress in many areas, he said, from downtown development to policing to school renovations. And all of this has been a result of the consensus DeStefano has been able to build.

“He held the city together in important ways,” said Alexander. “I give the mayor a lot of credit for his ability to manage the politics of the various groups in the city.”


Lyndon B. Johnson, brilliantly brought to life in Robert Caro’s Master of the Senate, was the consummate politician. He knew whose back to pat, whose hand to shake, which buttons to push, which levers to pull. The Texan said of himself: “I do understand power, whatever else may be said about me. I know where to look for it, and how to use it.”

Johnson saw steps ahead of his Senate colleagues. He had the vision and ruthlessness to wrestle autonomy away from the powerful Senate committee chairmen and appropriate that influence for himself as majority leader. As Caro writes:

“This would be difficult, for deceiving the southern senators meant deceiving men who were expert parliamentarians, expert legislators, masters of their craft. Masters. But not geniuses.”

DeStefano is not unlike Caro’s Johnson. He knows where to look for power, and he knows how to use it. He is not an idealist. He is a technician of power – tough, slippery, effective, a politician in the mold of Giuliani, the Daleys of Chicago, and Johnson.

Screen Shot 2013-04-24 at 2.13.45 PMPerhaps the best word to explain DeStefano’s long reign is “inclusivity,” but not in a kumbaya, feel-good way. Consider this rather elaborate simile, preached at a funeral for the Spanish King Philip II, in an 1598 sermon:

“The life of a king resembles that of a hand-loom weaver. … You may think that the weaver’s life is easy, because he works at home, sheltered, close to his loom; but in reality the task is very hard. He labors with his arms, but see his feet working the pedals while his eyes remain glued to the cloth lest it become tangled. His attention is divided among the many threads, some going here and others there, keeping his eye open lest any break.”

DeStefano has been at his loom for 20 years, trying to keep each of the threads in New Haven’s elaborate fabric from tearing. This has meant keeping the various constituencies happy, with appointments, policies, and economic investment. Each time one of the threads threatens to snap, DeStefano has acted just in time.

DeStefano’s successor will inherit both his triumphs and his failures. His political instinct and agility, however, is not transferrable with the simple swearing of the oath. Such a gift is possessed by only the rare politician. It’s one thing to win a city’s election. It’s quite another to become its master.


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  1. Informative and well written.
    “the 2009 Supreme Court case Ricci v. DeStefano. That suit involved 20 New Haven firefighters, 19 of them white and two of them Hispanic.”
    Wouldn’t that make 21 firefighters total?

  2. You forgot corrupt in your article’s explanation to how he remained in power for 20 years. Also that the former mayor was the last of the New Haven political machine, that hand-picked aldermen and city hall members. No mention of the 2011 summer campaign where 20 people ran in opposition of all things Destefano for the Board of Aldermen (19 of whom won in their wards). No mention of his weekly walks from City Hall to Bruce Alexander’s office, either.

    I think it is a joke that a mayor so hated by his city’s residents is now teaching a class at Yale. Was this visiting professor status allowed because he sold off New Haven to Yale whenever he could? As well as always putting Yale’s interests in front of that which would have benefitted the city and its residents?

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