The "what ifs" linger long after a visit with John DeStefano, now closing in on his final weeks after a remarkable 20-year marathon as mayor of the Elm City.
What if DeStefano, smothered by M. Jodi Rell during a disastrous run for governor in 2006, had managed to persuade more than Democratic stalwarts around the state that his vision was right for Connecticut?
The result could have been a Connecticut a little more like New Haven, a community of neighborhoods with a youthful vibrancy, from bikes to biotech, that shames other cities in the state.
Would we be grabbing hold of more of our young bright minds and attracting creative new businesses? Would teacher unions be working with the state on reform? Would we be carefully and strategically targeting the kind of industries we want to build our future economy around? Under Gov. DeStefano, we might even be talking about the real tax crisis facing Connecticut — reforming the colonial era property tax.
"How was I able to survive 10 election cycles? Part of it was recognizing the city was changing and reaching out to constituencies that were new,'' DeStefano explained to me as we ducked into Blue State Coffee on the edge of Yale campus one early autumn afternoon. "Leaders ought to lead. You've got to engage the electorate with ideas and direction."
And you've got to know when you can seize a moment.
When DeStefano embraced the idea of a residency card for undocumented residents in 2007, New Haven was criticized across the country. But the cards, which gave city residents the legal proof to do things like open bank accounts or to communicate with local police, are a so-what issue today. This year, the state legislature approved giving driver licenses to the undocumented while Congress moves closer to actually enacting immigration reform.
"The thing with immigrants, of course, was more a case of 'are we are going to welcome these folks?' They are central to the vitality of the city,'' said DeStefano, who announced earlier this year that he would not seek another term as mayor. "That, to me, was like going from nowhere [to going] forward to some place.''
Paul Bass, a New Haven journalist who has followed DeStefano for three decades, said the mayor's savvy embrace of immigration reform was both "his shining moment" and good for the city.
"When Danbury was kicking them out, he was bringing them in," said Bass, editor and founder of the New Haven Independent online news site.
"He's been a very good mayor. Not perfect. He learned a lot in office," Bass said. "He believes government can work. He goes against the modern American political assumption."
With New Haven's schools, DeStefano spent much of his tenure doing what mayors often do — putting up new buildings. But after years of seeing relatively little improvement in the students, he saw an opportunity in 2008, when the American Federation of Teachers was entrenched in an ugly standoff in Washington, D.C., and his own city schools were stagnating.
DeStefano, looking for that carpe diem moment again, invited AFT President Randi Weingarten to New Haven to help forge a new teacher's contract. The result, after months of negotiation, was a contract now cited as a model for all cities because it emphasizes teacher accountability — and job evaluations that include student performance — but makes educators part of the process. It stands in stark contrast to the state's education reform efforts, which unions have fought, bitterly at times.
"It was an opportunity to put this together and come up with a New Haven model and do something extraordinary," DeStefano says about the school contract. "I couldn't have done school reform in 2006. In 2008, we drove a big truck through that [open] opportunity."
So, while the "angry John" tales are legendary, the stories that matter are about a mayor willing to focus — and sometimes to re-focus — on what works in a diverse, 20-square-mile city of activists living in the shadow of Yale University.
"He seemed a little too inflexible at times,'' said state Rep. Gary Holder-Winfield, who briefly ran to succeed DeStefano earlier this year. "But you've got to give a lot of credit to the mayor. Whether you like his style or not, most people agree that he could run the ship."
There remains much unfinished work. Crime is still a major problem, though in DeStefano fashion, he has more recently re-emphasized community policing after years of cutbacks because city residents demanded it. In recent days, there have been two murders in New Haven, once again leaving politicians, including DeStefano, grasping for ways to make the city safer. This year in New Haven, the murder rate is up but overall crime rates — including non-fatal shootings — are down.
Meanwhile, under DeStefano leadership, taxes rose steadily in New Haven; this year alone local property taxes rose by 5 percent. The city's bond rating has also dropped.
And despite the national headlines for an innovative teacher contract, schools remain far behind in student achievement. As in the Hartford area, the New Haven region's poverty is concentrated in the city.
What seems different here, when compared with other cities in the state, is a larger sense that things are happening, that potential looms on the horizon. The intense competition to be DeStefano's successor proves that.
At the Downtown Crossing development, the new headquarters of Alexion pharmaceuticals will soon be finished, not far from the city's expanding medical district and the nearly $500 million Smilow Cancer Hospital completed a few years ago. The city's relationship with Yale, at a low point in the early 1990s after the stunning murder of Christian Prince, a sophomore lacrosse player, improved steadily under the partnership of DeStefano and Rick Levin, the university president who retired earlier this year.
"Look at the assets that New Haven has successfully built on over the last two decades,'' said Will Ginsberg, CEO of the Community Foundation for New Haven, pointing to the stability of city neighborhoods, growth in arts and cultural activities, expansion of the immigrant community and a solid relationship with Yale. "It's happened because there is leadership and stability.''
DeStefano swears to me there are no regrets at missing out on the governor's mansion, but then offers his own critique of Hartford. He scratches his head at the state's investment in the New Britain-to-Hartford busway, keno gambling and even a Springfield-to-New-Haven commuter rail line.
"I can tell you 10 reasons why I want to get to Boston quicker. I can't tell you a reason why I need to go to Springfield,'' DeStefano said. "Make an argument to me for Hartford to develop commuter rail along I-84. That I can almost buy."
He continues, our coffee long gone, but the public policy seminar just warming up. "A lot of people would say I was controlling and too much a my-way kind of guy, often times. Well, I felt like I was a guy with strong views."
DeStefano, the son of a city police officer, the Boy Scout who grew up to become mayor, plans to go to work for a local community development bank and spend more time with his wife and two adult children.
"Here's the bad thing you find out when you become mayor,'' DeStefano tells me before we stroll across the Green. "You piss a lot of people off. By the other token they also give you incredible gratitude. In a place like New Haven, you are able to do things that impact New Haven but are also megaphones for other issues, like immigration, school reform, school construction, the partnership with the university, biotech and the knowledge-based economy.
"It absolutely the best political job in the world."
Rick Green is political editor of The Hartford Courant and a columnist.