New Haven Politics
Some Final Reflections on Robert Dahl

Legendary Yale political scientist Robert Dahl, who died at 98 last week, made a name for himself as the high priest of the pluralist theory of democratic politics and governance, in which political actors function as intermediaries between competing factions without being captured by any of them. In doing so he made the structure of power in New Haven a defining case study in American political science. From a normative standpoint, pluralism was an imperfect elaboration of the ideals of democracy, and in the Dick Lee era that Dahl studied it led to such grave errors of judgment as the bulldozing of whole neighborhoods in the Orwellian name of ‘urban renewal.’


[Robert Dahl.]

Still, Dahl’s model described a vibrant democratic system in which the role of money in politics was muted and there was no ruling elite, at least not a permanent one. Citizens might not agree with every decision of government but they could always be proud of it, confident that their leaders were acting in good faith on a level playing field where political and economic interests of all stripes grappled as equals. Dahl’s last book was published in 2006, before “Too Big to Fail,” “Super PAC” and Citizens United” had entered the lexicon. In 2014 would he say — would he have said — that his faith in pluralism was unshaken, and would anyone believe him?

Learning To Stop Thinking Like An Appropriator
Transitioning from the legislative to the executive branch of government is never easy, but it causes the most severe seasickness for those who begin the journey as appropriators. 

Mayor Toni Harp appears to be regaining her footing with an outside-the-box appointment of one of her opponent’s top supporters and well-reviewed handling of the first major snowstorm of 2014; but nobody would deny she’s had a rocky start. While filling department head positions and navigating distractions caused by her former running mate (who is now city town clerk) have been challenging, they will pale in comparison to the unpleasant and thankless (sisyphean?) task of putting together a balanced budget for the upcoming year.
The mayor’s budget is due March 1 and will be followed by three months of finance committee hearings and negotiation with the Board of Alders. The critical date is actually February 5, when Governor Malloy releases his state budget proposal, which could be devastating to New Haven if it cuts funding levels for municipal aid. (A resolution from the Board of Alders, even a strongly worded one, is unlikely to substantially influence Malloy’s generosity or lack thereof.)
Harp’s first budget will pit instincts honed over many years as a member (and later co-chair) of the appropriations committee against the demands of running a city — and not just any city, but one that already has one of the highest property tax burdens in the region. It has long been understood that the sensitivities and sensibilities of the appropriator and the chief executive are differently calibrated. One of the seminal topics in American political science is the arcane set of unwritten rules by which appropriations get made: Richard Fenno’s 1966 book “The Power of the Purse: Appropriations Politics in Congress” remains a classic in the field, but you also have the committee-dominance model of Shepsle and Weingast, the floor-dominance model of Krehbiel, the party cartel theory of Cox and McCubbins, and Aldrich and Rohde’s conditional party government mode of appropriations. These various models mostly unite on the fact that the highly ritualized work of appropriators is governed by its own logic.
As an appropriator, Toni Harp is used to people coming to her for handouts.  The reason that the appropriations chairmanship she held for a decade is so coveted, second only to leadership in importance, is that it’s the first and last place hundreds of state-funded agencies and programs bring their collection plate. For a decade she was the rainmaker who could fertilize the parched fields, or leave them out to dry. Like King Lear dividing his realm among his daughters, she might choose to favor certain parties over others, but that shouldn’t be confused with fiscal discipline. If taxes went up, as they did in 2011 (by $1.5 billion), it wasn’t Toni Harp that got blamed. 
The mayor’s job is more demanding and less forgiving, at least where budgets are concerned. Every appropriator is also a legislator, and the legislature as a whole is accountable for sound fiscal management; but with 187 legislators for the state or 30 alders for the city, that accountability is diffuse in the sense that failure is always an orphan. Not so for mayors, who sink or swim by their budgets and bond ratings. If taxes goes up, the mayor gets blamed, and nothing will end a new mayor’s honeymoon faster than a ballooning mill rate. 

Where you stand depends on where you sit. Whether she likes it or not, the new mayor will have different priorities than when she was an appropriator — and that probably means a different set of friends and enemies. As she tiptoes through the budgetary minefield, the new mayor may find herself having to throw some old friends under the bus.
Field Collapses for “Launching-Pad” Senate District

The collapse of the field to replace Toni Harp in the state senate is probably best explained as a case of intense pressure from party bigwigs for unity going into a difficult re-election year for Governor Malloy.  With numerous bruising primaries in the 2013 municipal election cycle, party leaders have legitimate cause for concern about squabbling Democratic factions in many of Connecticut’s electorally important urban areas. From that standpoint it is hardly surprising to see Jackie James and late entrant Juan Candelaria getting ‘taken care of’ at City Hall or otherwise nudged out of the race. What is surprising about the sudden absence of competition is how strategically important the 10th senate district (covering part of New Haven and most of West Haven) has become: since it assumed more or less its present form in the post-1970 redistricting, it has been the launching pad for the careers of Joe Lieberman (served 1970-1980), John Daniels (served 1980-1990), and Toni Harp (served 1994-2014). After becoming Majority Leader of the State Senate, Lieberman went on to become Connecticut’s Attorney General and served four terms in the US Senate. Daniels defeated John DeStefano in a Democratic primary in 1989 and served two terms as New Haven’s first African-American mayor. Harp became the powerful co-chair of the Appropriations Committee in Hartford and just became New Haven’s 50th mayor. It is hard to think of another district in the state legislature that has a comparable record of occupants graduating to higher office.


If Gary Holder-Winfield wins the seat as expected in a special election on February 25, and holds on to it this fall, he will immediately join the top rank of possible contenders (Ted Kennedy Jr. and State Senator Gayle Slossberg are others that come to mind) for Rosa DeLauro’s congressional seat upon her retirement. Holder-Winfield would also become perfectly positioned to take another shot at the New Haven mayor’s office, which he briefly sought in 2013 before dropping out and endorsing Harp.

Unsolicited Advice for Mayor Harp: Manage Expectations (But Not Too Much)

If Mayor Harp were remotely interested in my advice for her first hundred days in office, I would remind her that politics is a game of managing expectations that entails consistently and patiently explaining to the electorate that deeply rooted institutions and structures of governance are often beyond the ability of any one person, even a chief elected official, to control; and that no politician ever takes office in a historical vacuum.

After a well-run campaign that heightened public expectations, New Haven’s first black mayor, John Daniels, was hobbled by several political hot potatoes he inherited from his predecessor Biagio DiLieto. One was a twice-postponed property revaluation that threatened to double or even triple many property-tax bills. Daniels responded to the massive budget deficit created by DiLieto’s postponed revals and tax giveaways to real estate developers, combined with the early 1990s recession, by laying off about 300 city employees. Budget austerity was painfully disappointing for some of Daniels’s strongest supporters, but what else could he have done in a crisis situation? Meanwhile, a federal order to replace old-style public housing projects with scattered-site housing led to Daniels’ good-faith effort to situate public housing in the predominantly white Eastshore neighborhood, an effort met with massive controversy and resistance that further handicapped his administration. And then of course there was the unfortunate reality that Daniels entered the mayor’s office just as America’s crack epidemic was taking off. As New Yorker writer William Finnegan poignantly recounted in chapter one of his book Cold New World, New Haven was hit as hard as any comparably sized city in the country. 


[John Daniels’s portrait in City Hall.]

Daniels left much to be desired as a leader and administrator, but in his defense he faced a ‘perfect storm’ of chronic structural impediments, on top of several catastrophic lightning strikes, none of which were of his own making. And it would be foolish to deny that racial prejudice added to the headwind he faced in his two unhappy terms. Needless to say, history is not a great respecter of the norms of political correctness. While Daniels couldn’t wave a magic wand and make all the structural challenges melt away, he probably could have done a better job managing expectations. 

Will New Haven’s second African-American and first female mayor find herself crippled by circumstances beyond her control? Will her historic mayoralty, like Daniels’s, become collateral damage of a lousy economy and a fiscally irresponsible, long-serving predecessor? To put it another way: with a full plate of daunting challenges dropped in her lap, how can she best manage expectations for her administration?

Harp needs to walk a fine line between lowering expectations and renouncing accountability altogether. Consider the following: you don’t have to be an accountant, municipal bond trader, or even an East Rock taxpayer to know that the City of New Haven’s finances are a mess. But to hear some people tell it, what is visible on the surface of the Department of Finance’s monthly reports is only the tip of the iceberg. In this telling, which was almost a shibboleth for the Kerekes campaign in 2011, the DeStefano administration covered up its gross mismanagement of taxpayer dollars by taking shady deals off the books or otherwise hiding debts and exaggerating assets. Harp and her team won’t know how bad things really are until a thorough financial audit is concluded. That could take months or even years. Maybe we will never know. 

That is what some will people around town will tell you, in what you might call a perverse form of managing expectations. But the ‘Mayor Madoff’ conspiracy theory is, in essence, a manifestation of DeStefano Derangement Syndrome. Is it possible that New Haven’s financial picture is actually worse than it appears? Anything is possible, but we already know that the city has the third highest net direct debt per capita debt burden of the country’s 250 largest cities — as computed by the Wall Street Journal according to publicly available data. It is no secret that the city’s bond rating was downgraded by all three different ratings agencies in the last year, because of a $500 million unfunded pension liability and a negative fund balance, with borrowing costs going up accordingly. Is the ‘tip of the iceberg’ not distressing enough?

Imagining DeStefano as a Madoff-like villain who dressed up the City’s precarious finances with smoke-and-mirrors accounting misses the point. Everyone knows where the big-ticket liabilities come from: namely, rising pension and health care costs. (Problems on the revenue side are equally daunting, but that is another discussion.) To suggest that a post-DeStefano forensic audit of New Haven’s financial problems will reveal anything new is to diminish the plenty-depressing reality of what we already know. 

During the campaign Harp was ambiguous about whether she would support defined-contribution pension plans for public employees. She indicated openness to a “hybrid” pension plan of some kind, but her wariness to offend public employee unions who supported her campaign heavily raised — and raises — questions about her seriousness and willingness to rectify New Haven’s long-term financial picture. In a profile of Harp just published by the Wall Street Journal, Harp already seems to be declaring victory on the pension front. Is this willful blindness, or perhaps managing expectations to an absurd extreme? Harp can try to blame DeStefano if, or when, her inability or unwillingness to adopt meaningful reform damages her political standing; but ultimately she will have nobody to blame but herself. Managing expectations is important, but not to the point where you relieve yourself of accountability for anything at all. 
Comeback Kid: How Martin Looney Became the Kingmaker in New Haven Politics

At the end of 2001 Martin Looney had reached the nadir of his professional career. He had lost a bitter primary to longtime rival John DeStefano in September, winning less than 40% of the vote and only a handful of wards on the east side of the city. The primary had been a slash-and-burn affair with many bridges burnt. His ally, Nick Balletto, would soon be deposed from his position as chairman of New Haven’s Democratic Town Committee for disloyalty in supporting Looney over DeStefano. 


Twelve years later Looney, who became Majority Leader of the State Senate in 2004, has emerged as the pre-eminent kingmaker in New Haven politics. When DeStefano announced last January he would not run for an 11th term, Looney was instrumental in getting his senate colleague Toni Harp (who entered the upper chamber with Looney in 1994) to throw her hat in the ring, once Jack Keyes (Looney’s law partner) decided against entering the race. Looney helped to line up support for Harp, including finding her a campaign manager (Jason Bartlett) who had run Looney’s mayoral campaign back in 2001. As Harp’s relationship with the unions has become slightly strained, Looney’s position has strengthened. He has become a broker between the different factions in her administration, her most powerful and experienced political adviser, and closest ally in Hartford. With Jackie James resigning from her position as chairwoman of the DTC to accept a post in the Harp administration, Looney’s longtime aide Vinnie Mauro is poised to become the DTC chair. That will give Looney significant leverage over local political matters as well as control over the largest bloc of Democratic delegates at state conventions. 
And of course Looney remains the second or third most powerful figure in the state legislature, which holds the purse strings for half of New Haven’s budget.
If anyone is now the “boss” of New Haven, it is Marty Looney, New Haven’s comeback kid.
Does Anyone in the Harp Administration Tweet?

So what’s with all the taxidermied old fuddy-duddies in Toni Harp’s fledgling mayoral administration? That is the question du jour in New Haven politics. To the extent that Toni Harp is resurrecting New Haven’s “old guard” Democrats from the grave by turning 165 Church Street into a geriatric ward for the likes of Chief of Staff Tomas Reyes (Board of Aldermen President 20 years ago) and Economic Development Administrator Matthew Nemerson (Chamber of Commerce President 20 years ago), it is not because of nostalgia for a brilliant heyday that never was (goodness knows the pre-DeStefano early 1990s weren’t a golden age), or because she believes (per Reyes) that experience matters above all else. It is, as they say, less ‘man bites dog’ than all that. Politics is about relationships, whom you trust, who’s in your rolodex or Favorites list on your iPhone. Because Harp ‘graduated’ from city government in 1993 when she was elected to the state senate, her relationships at the state capital have become diverse and multi-generational, but her point of reference for New Haven politics has been frozen in time, grounded in an era before the existence of social media, even before the existence of e-mail. 

To use what is either a very revealing or very frivolous generational marker for the Harp administration, there is a distinct absence of people on Team Harp who are users of Twitter. The popular social network of 140-character messages may have become an indispensable tool for politicos of the Cory Booker generation (paraphrasing Cole Porter, even the Pope and President of Iran do it), but neither Harp nor Reyes use Twitter at all (though Harp had a campaign account). Nemerson (@mattnemerson) hasn’t tweeted since June 24. Transition Team co-chairs Ed Joyner and Mark Sklarz don’t tweet. Longtime aide Phyllis Silverman doesn’t tweet. Harp campaign manager and new director of youth services Jason Bartlett doesn’t tweet. If there is any major figure in the Harp administration who uses Twitter, I don’t know about it. 
Using Twitter may not have anything to do with effective governance, but in the Age of Booker it’s a pretty solid indicator of who’s tuned in (for better or for worse) to the prevailing political zeitgeist, at least when it comes to technology and communications.
UPDATE: After this post was written, Mayor Harp joined Twitter (@mayorharp).
More Thoughts on the Upcoming State Senate Special Election…

A few thoughts about the special election to replace Toni Harp in the state senate, which is likely to NOT be the last special election in New Haven in 2014:

1) The election will most likely be held February 18 or 25 (assuming it takes place on a Tuesday — New Jersey recently held a special election on a Wednesday.) It will be 46-56 days after Toni Harp resigns from office, which is expected to take place January 1, when she is sworn in as mayor. If she resigns before that, the election could be held sooner, which might help Gary Holder-Winfield, who has been preparing to run for the seat since he dropped out of the mayoral race this summer. New Haven is already scheduled to hold ward co-chair elections on March 4 — but it doesn’t seem possible to push the special election that far back.
2) State senators represent approximately 100,000 constituents, slightly less than the size of New Haven (130,000). Yet while more than 20,000 people voted in New Haven’s mayoral election last month, the turnout in the special election will almost certainly be less than half of that. In the four state senate special elections that took place in Connecticut in 2012, 5000 votes was the approximate winning total in all four (which were all two-person races). With more than two candidates in the race for the 10th senate district (there are currently two, but more may emerge), the winning vote total could be as little as 3000. In November, mayoral candidate Justin Elicker won nearly 1/3 that many votes in a single ward (ward 25) that is part of the 10th senate district.
3) The CEP public financing grant for a special election is less than the grant for a regular general election, and less than a full grant because the 10th is considered a “party-dominant” district. In 2011 the senate special grants were $66,000 in non-party dominant districts. Because fundraising cannot begin before Harp resigns, and the candidates will need to reach the contribution threshold by the end of January in order to have their CEP funds available for the critical final weeks of the campaign, all the qualifying contributions will have to be collected in a short time period, about one month. As a mayoral candidate, Holder-Winfield took four months to gather enough contributions to qualify for a grant from the New Haven Democracy Fund. He will also have to gather petition signatures for the senate race, as he is not expected to receive the party nomination.
Reflections on the DeStefano Era (And the Limitations of Term Limits)

Like all long-serving politicians, ten-term New Haven Mayor John DeStefano was defined not so much by a particular set of values or policies as by his evolution, his pivots, his accommodations to the political zeitgeist. From Winston Churchill to Strom Thurmond to Jerry Brown, the most tenacious of long-serving career politicians are by definition chameleons whose stock-in-trade is adaptation to the demands of the era, even if it means swapping one ideology, or political party, for another. But DeStefano really seemed to raise political survival to the level of an art form, as he outlived scandal after scandal, a bitter primary against a popular rival, a doomed run for governor, stinging defeat at the United States Supreme Court in a discrimination case that cost the city $5 million, and the coming and going of at least two different political machines. Along the way he evolved from an Ed Koch / Dan Rostenkowski Democrat to a thoroughly contemporary exponent of urban neoliberalism in the vein of Booker and Bloomberg, mirroring the tectonic drift of the national Democratic party. Perhaps it wasn’t so much an ideological leap as the cultivation of a deeper-pocketed set of friends, and a new set of enemies armed with a sense of betrayal.

But DeStefano didn’t just surf the zeitgeist. Sometimes his pivots were genuine acts of learning from mistakes. In that sense DeStefano’s leadership is actually a good argument against term limits: not because he was an ‘indispensable man’ who resurrected New Haven from its Detroit-like early-1990s depths with the far-sightedness of his vision and the force of his will, but because like all great political survivors he was a master of course-correction. DeStefano wasn’t quite a great mayor, but he will be remembered well fifty years from now, because he was that rare species of politician capable of failing upward.

And you don’t need to read this opposition research memo prepared for the 2006 Jodi Rell campaign to know that there were a lot of mistakes and failures to learn from: the 1990s corruption scandals that seemed to miraculously circle around the mayor but never touched him; the collapse of community policing; the Ricci case; the disastrous Long Wharf Mall proposal, that even DeStefano himself later admitted was a boneheaded idea doomed to implosion from the start.


But after the federal subpoenas started flowing, he replaced the rotten apples in his administration with competent technocrats. His 1989 loss to Daniels and close-call against Looney in 2001 hobbled his confidence enough that he could never quite ditch the likes of Boise Kimber and other ‘machine’ parasites who provided succor to his campaigns, but as mayors in Hartford, Bridgeport and Waterbury were being perp-walked out of city hall in handcuffs, New Haven looked squeaky clean by comparison. After realizing that huge tax subsidies were financially unsustainable and promoted bad development, he changed the way development deals in New Haven were structured. After years of defending an indefensible status quo in New Haven’s public schools, he initiated a nationally recognized school reform effort with — no mean feat — genuine buy-in from teachers and community groups. After years of being criticized for his top-down management style, he learned to listen more to the neighborhoods. His brush with humiliating defeat in 2011 — almost losing to political newcomer Jeffrey Kerekes, and losing control of the Board of Aldermen to a union-backed faction — forced him to heed calls from the neighborhoods to bring back community policing. By the end he even seemed to warm to the idea that meaningful public participation in big city planning projects was a good thing, to the point of holding a public design charrette on overhauling the downtown street grid.

It is easy to dismiss some of DeStefano’s evolutions as acts of political expediency. His belated embrace of “education reform” after 15 years in office was clearly informed by federal government funding priorities, in precisely the same way his signature $1.5 billion school construction program would never have gotten off the ground if the state weren’t footing 80% of the bill; and his commitment to “new urbanist” ideas like highway removal extended only as far as the nearest TIGER grant. Of course, sometimes the free money proved not to be free. And many people felt that the tail wagging the dog — DeStefano coming around to doing the right thing only when the financial and political incentives were right — was probably not the best way to run a city.

On the other hand it would be foolish to suggest that going on national television, as DeStefano did in 2011, to argue for undocumented immigrants having the right to vote in local elections was about fishing for grant dollars or electoral advantage. His strong support for immigrant rights may have helped replace some of his support in the black community, which had been eroding for years, with Latino support, but the net political impact was clearly harmful when he ran for governor and neutral at best in New Haven. He certainly didn’t need to subject himself to the torrent of abuse and hate mail he received in response to the resident ID card program and the voting proposal unless he really believed in the larger cause as bedrock of his mayoral legacy. When DeStefano really cared about an issue, as he did with immigrant rights, he looked like a great mayor; and left many exasperated progressives wishing he pursued more issues with that kind of sustained creativity and zeal.

DeStefano’s long tenure is sometimes used as an argument for term limits. But if he had been kicked out of office ten years ago because of an arbitrary cap on a mayor’s ability to serve consecutive terms, he would have been denied the opportunity to learn from his mistakes, and the city would be worse off because of it.


Final Observations on ‘Bellwether’ Wards And a Politically Divided City

A few observations about yesterday’s historic election in New Haven:

* Turnout seems to have bottomed out in New Haven municipal elections and is headed in the right direction again. More than 20,000 votes were cast on Tuesday, about 35% higher than in 2011 and the most in a municipal election since 1989. As turnout in municipal elections has fallen over the last couple generations, the disparity between turnout in presidential versus off-years has grown. That disparity is now declining as well.
* Elicker increased his vote total by about 6000 from the primary to the general, while Harp increased her total by about 4000, so Elicker almost certainly won the majority of votes of people (mostly unaffiliated and Republican, but some Democrats as well) who voted only in the general. If he had received all of the votes of people who voted for Henry Fernandez and Kermit Carolina in the primary, and no other votes, he would essentially have tied Harp or narrowly lost.
* Both Elicker and Harp did very poorly in some wards, but Harp had a higher floor. Elicker got fewer than 100 votes in seven different wards. Harp’s lowest total in any ward was 188. Harp lost Ward 18 (Morris Cove) by more than 600 votes, but she still got nearly 300 votes there.
* The city is politically (and racially, economically, socially, etc.) divided. Wards 8 and 26 were “bellwethers” where Harp won by narrow margins similar to her citywide margin. They also happen to be racially diverse; and interestingly they are the home wards of Mike Smart and Toni Harp, respectively. But in most wards one or the other mayoral candidate won big.
* Both charter revision questions were approved overwhelmingly, which is probably testament to the substantial resources the party machine invested in getting them passed, dispatching pollstanders in every ward with “Ask Me About Charter Revision” buttons and palm cards advocating a yes vote on both questions. It was sometimes painful to watch complex aspects of municipal law being explained to voters by pollstanders who were often fuzzy on the details of charter revision themselves. But they proved reasonably effective in getting people to vote!  In Hartford there was no such effort, and fewer than 2% of people voted on the charter questions.

Toni Harp: The Female Obama?

One of Toni Harp’s keys to success on Tuesday was a very strong base in New Haven’s African-American community, especially among African-American women, for whom Harp’s candidacy resonated on a deeply personal level. But equally important was the consistency of her appeal across New Haven’s 30 wards. That’s not to say she didn’t lose some wards by considerable margins — for example, Morris Cove’s Ward 18, where Elicker trounced her by more than 600 votes (the highest discrepancy between the two candidates in any ward). Yet while Elicker received fewer than 100 votes in seven different wards, Harp’s lowest total in any ward was 188. Without exit polling we can only speculate about the racial breakdown of Tuesday’s vote, but the ward-level results indicate that while Elicker clearly won the white vote, Harp did not elicit the kind of ‘white backlash’ that often dooms minority candidates. As with Obama in 2008, that speaks both to her personal qualities — Harp may be polarizing in some respects, but she is not racially polarizing — and to the campaign that she ran, which mirrored Obama’s with her exceptional knack for maintaining a strong bond with her African-American base without compromising her ability to attract support from the political and economic establishment, including a lot of rich white people. Comparing Harp to John Daniels across a generation gives a whiff of the meaning of “Post-Obama Era.” Both Harp and Daniels became mayor of New Haven after serving as state senator from the tenth district. Following the Tom Bradley model, Daniels’s historic campaign in 1989 to become the city’s first black mayor successfully attracted white liberals into a winning multi-racial coalition, but Harp went beyond that, as Obama did, in securing support not only from across the entire Democratic Party establishment, including the local party machine (which virulently opposed Daniels), but also from wealthy white donors representing business and real estate interests. She proved to be a prodigious fundraiser, collecting checks from an impressive variety of political action committees, and her cautious campaign, in which she hewed to the center and surrounded herself with people intended to reassure the business community and bond markets, was (like Obama’s in 2008 and even more so in 2012) very much an establishment affair. When Daniels was elected, he said “The Daniels administration will belong to the people of New Haven, not the so-called bosses… or the big campaign contributors.” He might have been referring to some of the people at Harp’s victory party at Kelly’s 24 years later.

[Photo credit: New Haven Independent.]
In Harp’s first campaign (for alderman) in 1987, she ran on both the Democratic and Green Party tickets. In addition to the African-American community, her base skewed heavily towards left-wing peace and social justice activists, the same folks who gave Daniels the white support he needed in 1989. At various times she has been attacked for associating with Communist Party members and institutions. But over her many years in office she evolved and society evolved, so that by the time of her mayoral run in 2013 she was the establishment figure, while the white male in the race was the scrappy, controversial, underfunded outsider. It’s almost impossible to imagine that occurring a generation ago. Race still matters in New Haven politics, as it does everywhere else, but there is something gratifying in the fact that, in the post-Obama era, it doesn’t seem strange at all that a black woman could be the frontrunner from the moment she entered the mayoral contest, a fundraising powerhouse and electoral juggernaut who made history simply by winning a race everyone thought she would win.