The New Haven and Yale of 20 years ago are a far cry from the city and University of today.

Twenty years ago, a committee was searching for a replacement for then-interim University President Howard Lamar. Across the New Haven Green in City Hall, John Daniels, the Elm City’s first black mayor, struggled with seemingly insurmountable budget problems and New Haven’s ranking as the seventh-poorest city in the country. Unemployment rates soared in the face of a gutted manufacturing sector, and with tough economic times came other ways of making a living. In New Haven, that meant a growing drug trade and higher crime.

High unemployment may have contributed to a record high of 34 homicides in 1991, a rate unmatched until 2011. Among those 34 homicides was Yale student Christian Prince ’93, who was shot to death on the steps of St. Mary’s Church on Hillhouse Avenue in February of that year.

When Mayor John DeStefano Jr. and University President Richard Levin took office within a few months of each other two years later, neither had an easy job. Levin faced old, deteriorating buildings, persistent labor union strikes, an $18 million deficit and fresh fears about the safety of Yale’s campus in the wake of Prince’s death. DeStefano, meanwhile, had to fight the typical urban problems of deeply entrenched crime, poverty, unemployment and school dropout rates from a mayor’s office that had built a reputation for inertia.

“Intangibly, the spirit in New Haven was a downbeat civic spirit. It was one of ‘How do you manage decline?’” said University spokesman Michael Morand ’87 DIV ’93, a former Ward 1 alderman.

In the past decade, a revitalized downtown, a jobs-heavy science park, a newly created “jobs pipeline” and a plan to redevelop Route 34 to focus on New Haven’s emerging biotechnology industry have lifted the city’s economic prospects. Today’s town-gown relations, too, would be nearly unrecognizable to anyone 20 years ago — in place of the antipathy that defined the past, Yale and New Haven now cooperate on initiatives like the New Haven Promise scholarship program and the Yale Homebuyer Program, which saw its 1000th participant last year.

While Levin announced his retirement in August, describing his 20th anniversary in office as “a natural time for a transition,” DeStefano, who will pass the record for longest time served by a New Haven mayor on Oct. 4, has shown no such inclination to leave. An invitation to DeStefano’s birthday party in May asked attendees to support the mayor’s reelection — complete with a campaign email address — and the mayor recently visited a senior housing complex carrying “DeStefano for Mayor 2013” bags.

Despite widespread acknowledgement among city residents that the mayor has played a significant role in the city’s recent upswing, DeStefano won his election last fall by the narrowest margin of his tenure — 55 to 45 percent — despite higher name recognition and a vast cash advantage. At the same time, a slew of labor union-backed aldermanic candidates defeated many DeStefano allies on the Board of Aldermen during last September’s primary election, giving Yale’s unions a majority on a board that has traditionally been perceived as a rubber stamp for the mayor.

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“After 20 years, people are a little tired of one-party rule, and maybe even one-person rule in this case,” said Charlie Pillsbury, a former Democratic Party activist who ran twice for the Board of Aldermen as a Green Party candidate.

With his hold on office growing increasingly tenuous each election cycle, DeStefano’s next race may be his last — forcing a city whose politics have become synonymous with a single person to consider a future without him. DeStefano’s success next fall will depend on how his legacy is judged, a subject on which local citizens, political observers, city officials and DeStefano himself disagree.


New Haven’s decline began decades before DeStefano entered politics.

Former Mayor Richard Lee, who began his 16-year stint at City Hall in 1954, focused his efforts on lifting New Haven out of poverty by enacting federally funded urban renewal projects, razing lower-class neighborhoods and replacing them with new infrastructure, most notably highways. At the time, New Haven — which received far more urban renewal funds per capita than any other American city — was hailed nationwide as a “model city.” Lee, admirers claimed, had created the first slumless, modern city, and many expected other cities to follow the Elm City’s example.

But the feeling of success was short-lived, as employment declined and urban renewal was revealed to be less successful than initially expected. Poverty soared, and many city residents fled the city for the surrounding suburbs. When Lee left office in 1970, his attempts at urban renewal were largely regarded as failures. His early optimism was destroyed by the city’s accelerating descent into poverty and crime: “If New Haven is a ‘model city,’ God help America’s cities,” he said, according to a book by School of Management professor and former New Haven Chief Administrative Officer Douglas Rae.

DeStefano began his political career in Lee’s shadow. He worked for nine years as one of Mayor Ben DiLieto’s chief budget aides, before running against John Daniels in the 1989 Democratic primary following DiLieto’s retirement. DeStefano lost by a wide margin in an election that drew about 70 percent of the city’s voters.

Jim Farnam, who worked for the DiLieto administration for 10 years until 1989, said DeStefano’s defeat was caused by an unusual coalition of DiLieto’s detractors and black voters. DeStefano, he said, was perceived as “DiLieto’s guy,” a costly association.

But Daniels had been “dealt a tough agenda,” Farnam said, and DeStefano decided to run again in 1993 after Daniels announced his retirement.

“[DeStefano] was perceived as a technocrat with his accounting background,” Farnam said. “The perception was that he was some kind of a manager who would come in and fix things. There were a lot of issues that people had with some of the things Daniels did.”

With the backing of the Democratic machine, DeStefano defeated John Yopp with an overwhelming 80 percent of the vote in the Democratic primary.


DeStefano faced a series of political challenges immediately after he took over the mayor’s office on the second floor of City Hall, including a court ruling ordering the city to pay the Board of Education millions of dollars in a settlement. But being new to the role, DeStefano said, meant people went easy on him.

“I was new. It’s good being new,” DeStefano said. “I think an advantage I had was I had been around in the bureaucracy for 10 years and sort of knew my way around.”

He saw a few successes during his first term — including two budget surpluses, $2 billion in savings during labor negotiations, an end to tax hikes and an overall expansion of city services — so his reelection seemed guaranteed. Having delivered on many of his campaign promises, DeStefano defeated Republican challenger Ann Piscottano with 72 percent of the vote.

But one of his most noticeable successes, the drastic drop in the homicide rate, was not the result of any of his own efforts. It was thanks mostly to the Daniels-era arrival of New Haven Police Department Chief Nick Pastore, who implemented a community policing strategy that encouraged officers to form connections with the communities they patrolled. Neither does DeStefano deserve full credit for the dramatic turnaround of New Haven’s relationship with Yale, the mayor admits. In a break from their predecessors, DeStefano and Levin had made a point of working with, and not against, each other, and both leaders took the mayor’s overwhelming margin of victory as a clear mandate to continue their partnership.

“I’ve developed an excellent working relationship with Mayor DeStefano. I find him a person with tremendous energy and with a real vision of improvement for the city,” Levin told the News at DeStefano’s 1995 victory party. “I look forward to another two years.”

By the 1997 election, New Haven had seen such dramatic improvement under DeStefano that he ran unopposed in the Democratic primary, winning the general election with 79 percent of the vote against four independent challengers.

“We haven’t won the total battle yet, but the mayor’s done a good job,” Morand told the News at DeStefano’s victory party that year, but his opponents complained about DeStefano’s reliance on the “old machine” of the Democratic Party.

During his 1999 reelection campaign against James Newton, DeStefano argued that New Haven had completed an “about-face” under his stewardship. During his 1997-’99 term, DeStefano spearheaded the renovation of nearly all of the city’s schools. Will Ginsberg, who worked with DeStefano in DiLieto’s administration before heading the Science Park Development Corporation, called that initiative “nothing short of extraordinary.”

These successes were enough to win DeStefano reelection against Newton, though he did so by his tightest margin yet, and lingering memories of the 1998 disappearance of $2.3 million of federal funds for DeStefano’s anti-blight Livable City Initiative (LCI) tarnished his image in that race.

The scandal threatened to overwhelm City Hall — a U.S. Attorney’s Office investigation of the initiative was underway — but DeStefano saved face by dismissing top LCI officials and placing Henry Fernandez LAW ’94 at the agency’s helm. That move allowed DeStefano to stave off Newton’s charges of corruption, winning his fourth term by a wide margin, with 62 percent of the vote to Newton’s 38 percent.

In 2001, DeStefano faced State Senator Martin Looney in the city’s Democratic primary in the most expensive campaign in New Haven history, with over $450,000 raised for the mayor’s reelection fund. Looney, who had then served 21 years in the state legislature, insisted that New Haven residents wanted a change after eight years under DeStefano, and criticized the mayor for his corruption scandals, poorly-performing schools and a failed proposal for a Long Wharf galleria.

But DeStefano asked voters to remember how far the city had come under his stewardship, emphasizing his point in a speech at Bella Vista the night before the election.

“Look at where we started eight years ago,” DeStefano said, the News reported. “I think I’ve done a pretty good job.”

Voters agreed, and the DeStefano won reelection with 62 percent of the vote in the primary. Looney, though, argued that his loss was in part to blame on the terrorist attacks on the World Trade Center that had occurred the same day, which he said suppressed turnout.

In the shadow of those attacks, which took place just 90 miles south of New Haven, DeStefano told attendees at his post-election party that his victory was a “clear and strong message” from voters on his record.


After winning his 2003 election against an independent challenger with 88 percent of the vote — an all-time high — DeStefano decided to try his hand at higher office, launching a campaign for governor against Republican incumbent Jodi Rell.

He said he saw the campaign as a “natural extension” of the changes he had enacted in New Haven. But after spending most of his campaign funds in a bitter primary battle with then-Stamford Mayor Dannel Malloy, DeStefano’s cash-strapped campaign was overwhelmed by Rell’s attack advertisements and he only received 35 percent of the vote. It was DeStefano’s first and only run for state office.

His gubernatorial campaign was perhaps the high-water mark of DeStefano’s time in office — in its aftermath, critics called him an absentee mayor and some of his previous successes began to unravel.

Pastore, the driving force behind community policing, resigned in 1997 after admitting to fathering a child with a prostitute. With his absence came a shift in department priorities away from community policing. This was not a conscious choice, DeStefano said, but rather the result of revolving police leadership.

But an increase in the city crime rate lagged a few years behind the change in police strategy, and it took nearly a decade after Pastore’s exit for the city to recognize it had a crime problem.

“It’s the old story that if you throw a frog into a pot of boiling water it’ll jump out, but if you put it in a pot of cold water and turn up the heat it’ll boil to death,” DeStefano said. “I think that sometimes in your life or in a community’s life, change is imperceptible and so incremental so as to not be detectable … I think, with community policing, my antenna didn’t pick that up.”

The city’s schools, too, lost their upward trajectory. While educational facilities were new, scores remained below state and national standards.

Another area of mixed success was election reform. After the expensive race against Looney and his administration’s corruption scandals, DeStefano pushed for the creation of the New Haven Democracy Fund, which provides public matching funds and grants to mayoral candidates who agree to certain restrictions on fundraising. DeStefano, who trumpeted the Fund as a victory for clean and transparent elections, used money from the Fund in his two following reelection campaigns.

But in 2011, facing an anti-incumbent mood and a tough challenge from budget watchdog Jeffrey Kerekes, the first challenger to qualify for Democracy Fund money, DeStefano abandoned the Fund. He claimed it “[didn’t make sense]” any more, an explanation New Haven Independent editor Paul Bass called “phony.”

“[DeStefano] completely sold out on public financing,” Bass told the News. “He abided by it until he had a serious challenge, but he immediately gave it up when he thought his job might be threatened.”

Without the limits imposed by the Democracy Fund, DeStefano outspent Kerekes by a factor of about 20, ultimately winning the race by less than 10 percent for the first time since he was elected.


With almost 20 years in office behind him, DeStefano has seen his share of difficult days. But his success at remaining in office may have stemmed just as much from skilled political gamesmanship as it has from tangible achievements.

A large part of that prowess is evident in his ability to build coalitions, a skill that he used to win his first election in 1993 and which he has continued to refine. The mayor, Morand said, has been remarkably good at governing a city without a racial or ethnic majority, adding that DeStefano can be friends with — or enemies with — someone regardless of their class, neighborhood or ethnicity.

“[DeStefano’s] very astute in the way he’s kept his coalition together,” Farnam said. “He’s managed to keep the black community largely supporting him over any other challenger because of his relationships he’s built up over years in the community, his relationship with [African-American superintendent of New Haven Public Schools] Reggie Mayo, who helps deliver the sort of older, old-line black community.”

This penchant for coalition-building has earned him a robust fundraising operation that kicks back into gear every two years. But much of this fundraising, according to Bass, is “hypocrisy.” A large portion of the money DeStefano receives in every campaign is donated by city employees and contractors doing business with the city, a practice that Bass said goes against the spirit of the clean election laws DeStefano has advocated.

“I think the way he raises money is legally corrupt, the way he shakes down people who depend on him for their livelihood,” Bass said. “It’s morally bankrupt because of the way he positions himself as a reformer who pushes for clean elections.”

But DeStefano disputed those charges, pointing out that neither his campaigns nor his office has ever been found guilty of corruption. As for fundraising, he argued that his campaign has never knowingly broken the law.

“We follow the rules as they’re set out, we follow them to the letter,” DeStefano said. “When we make a mistake, we try to correct it.”

More recently, DeStefano heeded the political winds following last year’s Democratic primary, where he won a plurality but failed to secure a majority. With a slate of labor-backed candidates calling for a return to community policing after a year of high crime, DeStefano brought back community-policing champion Dean Esserman, one of Pastore’s former assistant chiefs, to head the NHPD.

Then, with a new Board of Aldermen focused on the creation of a “jobs pipeline” to prepare and connect New Haven residents with local jobs, DeStefano adopted the idea in his February State of the City speech. With his weight behind the initiative, it was enacted by a unanimous vote of the Board of Aldermen earlier this month. While many new aldermen were elected last fall on a wave of anti-DeStefano sentiment, DeStefano and the Board have seen eye to eye on almost every policy question.

“DeStefano’s very good at seeing how politics change, how the issues change and understanding what kind of policies and coalitions keep him in power,” Bass said. “He’s good at reinventing himself, paying attention to issues and responding to what people want.”

For all his political skills, DeStefano considers policy more than most public officials, Bass said, and is effective at achieving the results he wants. It was the mayor’s interest in progressive policy that led to some of the more notable achievements of his tenure, including the school reform effort that led to what many have called a breakthrough teachers’ contract in 2009, as well as the Elm City Resident ID Card, which provides documentation to city residents whether or not they reside legally in the U.S.

This interest in progressive policy, DeStefano said, came out of his work at City Hall under DiLieto in the 1980s.

“In order to be here 20 years and be relevant to the people who live here, I think you have to be open intellectually and emotionally to what people are facing, and recognize the challenges of 2012 are different from the challenges of 2002 or 1992,” DeStefano said. “If you’re going to be able to stick around, you have to be able to engage things.”


Acknowledging the desire among many city residents for a fresh face in the mayor’s office, DeStefano said his time in office has offered him a perspective on “what works and what doesn’t work.” Still, he said, longevity breeds complacency.

“It’s important to grow with your city: people who live here and work here are different than the people who were here 20 years ago,” DeStefano said. “I think when you’ve been around for a long time you run the risk of isolating your relationships.”

Over the next 20 years, New Haven will face a whole new set of problems. Cheap housing stock, DeStefano said, will will continue to attract many to the city, where they will likely face a gap between the skills they possess and the type of work available. With New Haven’s growing reliance on its education and medical sectors, DeStefano said he sees that gap quickly widening.

This issue, however, may not be DeStefano’s worry much longer. While no one has yet declared their candidacy in next year’s mayoral race, an August phone poll by Yale’s unions for their internal use asked city residents for their opinions on DeStefano, Kerekes, Fernandez, State Reps. Gary Holder-Winfield and Toni Walker, State Sen. Toni Harp, Board of Aldermen President Jorge Perez and Greater New Haven NAACP President Jim Rawlings. Most of the names in the poll are recognized citywide, suggesting potential mayoral candidates in next fall’s election.

DeStefano, though, said he has set no limit on the time he would spend in office. He will leave City Hall, he said, once he decides he is no longer serving a useful purpose and enjoying his position — or if he should lose an election.

“I don’t think it’s so much the time [spent in office], I think it’s whether you’re relevant and whether you can derive satisfaction,” DeStefano said. “Whether you’re actually a part of solutions and helping people accomplish their aspirations, whatever that may be: starting a business, going to school, having a splash pad in their neighborhood, getting their potholes fixed.”

While he said he is most proud of New Haven’s transformation into an “opening, welcoming community” to immigrants and other groups, DeStefano said he won’t be giving much thought to his legacy once he leaves office. The only people whose opinions concern him are his wife, children and other loved ones.

But that hasn’t stopped others from opining on the mayor’s tenure.

“You can quibble with any one thing or things he’s done,” Farnam said. “But overall he’s guided the city well through very tough times.”

“He’s not only been mayor for 20 years but he’s provided strong, effective leadership in this community for 20 years,” Ginsberg added. “Not many communities have been that fortunate, I think — what he chooses to do with [that leadership] remains to be seen.”