John DeStefano Jr. has ruled New Haven for two decades, making the mayor’s office as powerful as it’s even been. He’s made enemies, but achieved a lot along the way. Feet down the tiled hallway from New Haven Mayor John DeStefano Jr.’s polished office, a group of volunteers, fueled on coffee and personal agendas, worked in a conference room last April to revise the city’s charter— their very own constitution. Many of them had the same goals as the original drafters of the Constitution—to restrict the powers of the king. The city’s splintered charter revision commission mirrors the schism of opinions on the 10-term mayor. There are those who believe his hand in everything from education to development has done the city well, while there are those who dub him a dictator who reigned over the Elm City. As DeStefano prepares to leave his downtown office and swap his political title for one in the banking industry, his legacy features a long list of successes as well as failures, obstacles and reforms that will still be works in- progress well after his departure. His reputation as a political powerhouse has been a result of years of careful, persistent mining of relationships—such as with longtime Yale president Richard Levin. It’s been manifested in major city policy changes as well as 10 elections where the incumbent was unbeatable. The night after he made history in November 1993, securing the widest margin of victory of any mayoral race in city history, the mayor-elect sat confidently in an office chair at campaign headquarters on Whalley Avenue, his feet resting on the desk. “I’m really excited to start governing,” he said hours after securing victory. Governing is precisely what he’s done, and like all elected officials, he’s faced the challenge of doing too much or not enough. Although there are serious issues facing New Haven—including high taxes and crime rates—it has become a model for school change and immigration reform under DeStefano’s thumb. In August, the city held a ribbon-cutting opening a new school in East Rock, the 37th project funded by the city’s $1.6 billion school reconstruction plan started in 1995. Yet the city still languishes to close its achievement gap, one of its primary education goals. Shovels are also in the ground to bring companies to the city as promised 20 years ago, and reforms in other areas, including the police department, abound. He has spearheaded immigration reform in his culturally diverse metropolis, making it among the first in the nation to offer undocumented immigrants identification cards. Within his first days in office, DeStefano spoke of the biotech industry as a possible savior to the city’s weak economy. That vision may not be fully realized until 2015, after DeStefano’s departure, when Alexion Pharmaceuticals finally opens its doors as anchor of one of the New Haven’s largest developmental undertakings, Downtown Crossing. That project—another ambitious vision—will replace the Route 34 highway corridor with boulevard streets and commercial and residential development. Convincing the state Department of Transportation to eliminate an entire state highway for economic development is just another example of DeStefano exerting his political clout on New Haven’s behalf. The move angered motorists; the mayor spun it with rhetoric about job creation and increased business opportunities, and it eventually was approved. DeStefano’s biggest political challenge came in 2011, when Jeffrey Kerekes, a budget watchdog, volleyed to unseat him, charging that people were tired of DeStefano’s overarching rule, telling supporters, “I will treat this city as one I live in, rather than one I reign in.” DeStefano bested Kerekes by 1,600 votes. In November, voters will not only elect DeStefano’s successor, but when they vote on the charter revisions, they will be voicing their opinion on how much power a mayor should wield. “We have a very strong may orally run city—and DeStefano took full advantage,” says Gary Doyens, member of New Haven Citizens Action Network, a citizens’ watchdog group. “He consolidated power and strength. He wielded it from zoning and policy to the board of aldermen and all the committees. There wasn’t anything he didn’t control directly or indirectly.” HOW TO READ THE CHART The chart at right shows the Connecticut's eight cities. The best possible rating is 1 and the worst is 8. For information on the sources used to compile this chart, please see page 49. Thanks largely to thriving local economies, good local schools and relatively low crime rates, Stamford and Norwalk earned the top two spots in our inaugural ratings of the state’s eight biggest cities. It’s probably not a coincidence that Stamford, which is growing faster population-wise than any other city in the state, earned the top spot. The City That Works is the state’s hub for financial services jobs, with UBS and RBS providing hundreds of high-paying jobs downtown. NBC Sports recently moved its headquarters from New York, and Bridge water Associates, a hedge fund with more than 1,000 employees, is scheduled to move to Stamford from Westport. Stamford also has the lowest crime rate in the group and ranks second in both culture/leisure and education. Norwalk, just two towns to Stamford’s east, tops the group in education and civic engagement and ranks second in economy and third in crime.