Trading Places

John DeStefano is confident, and there’s no reason he shouldn’t
be. Since he became mayor of New Haven in 1994, he hasn’t faced
a serious challenge to re-election, reigning from his office
overlooking the Green with apparent immunity. Despite frequent
allegations of corruption and numerous scandals in his administration,
potential opponents have mostly opted to stay out of the fray.

Martin Looney is confident. He is a popular state senator who
has been active in local politics for a quarter-century. He also
has a successful law practice, teaches classes at two local colleges,
and thinks he can unseat DeStefano in 2001. And why not? Jim
Newton proved that the mayor was vulnerable by winning almost
40 percent of the primary vote in 1999-and that was without any
major endorsements and with relatively little money. Looney has
much more of each.
This September, DeStefano and Looney will face off for the Democratic
mayoral nomination. DeStefano hopes to take credit for New Haven’s
recent economic improvement-he promises it will continue if he
is re-elected. Looney claims that eight years of corruption and
scandal have been enough; the city has improved, he argues, in
spite of the current administration. Ask the candidates to get
much more specific, and the details become fuzzy.
Traditionally, candidates for mayor of New Haven have fallen
into two categories: the candidate supported by the Democratic
party and the candidate who claims to be the outsider. Usually,
they are easy to tell apart: Two years ago, Jim Newton did not
have the support of any party leaders, while the mayor’s campaign
was managed by the Democratic town chairman, Nick Balletto. But
this time, with the mayor challenged by a well-liked state legislator,
the incumbent may end up playing the role of the outsider. Balletto
has declared himself neutral, and local Democrats are slowly
dividing into two camps, preparing for what could become a hostile

"I’m getting a little pissed off." The mayor’s distinct
voice travels from his office through the reception area. It
is late October, and he is on the phone discussing the situtation
of a local homeless shelter. "Who’s in charge of this? They’ve
had four years to deal with this already," he yells into
the receiver. The phone conversation ends, and a couple of minutes
later, the mayor steps from his office. "Can I go to the
bathroom?" he jokes with one of his assistants. "Yeah,
it’s allowed," the assistant replies.
The mayor has not run the city of New Haven for the last seven
years on charisma and congeniality. He doesn’t court the press,
and much of the time the media has responded in kind. But DeStefano
doesn’t seem to mind-he simply tells his mom not to read the
New Haven Advocate. DeStefano’s supporters know that he doesn’t
go out of his way to be delicate, or even tactful. "He’s
gotten calloused about making decisions that have to be made
but will piss people off," says Matthew Nemerson, former
CEO of the New Haven Chamber of Commerce. "And he doesn’t
tell them he’s sorry about it. [DeStefano] has presented an image
of himself that is tough and unemotional. A lot of people have
assumed he’s arrogant and uncaring," Nemerson adds. "I
don’t think that’s true, but he comes off that way."

Martin Looney sits at a conference table in his Orange Street
office across the street from City Hall, with his hands folded
on the table. At 52, Looney is seven years older than DeStefano.
His smile and his smaller stature make him a less intimidating
presence than the mayor, and while DeStefano expects people to
know what he’s accomplished and dismisses those who do not, Looney
wants to explain to everyone why he should be mayor.
"I think the city is prepared for a change," Looney
says. "There is a loss of energy," he adds, speaking
of DeStefano’s City Hall. With two decades in the state legislature
and prior experience in city politics, Looney thinks he is just
the person to bring a new attitude into the city government.
And Looney and his supporters offer other reasons why the mayor
should lose his job. DeStefano, they say, does not play well
with others.

Last year, DeStefano sent a letter accusing Looney of shirking
his duty as a state senator by not bringing adequate state funds
to New Haven. According to DeStefano, he was merely doing his
job. "As quarterback of the city . . . I’m here to see that
this is a healthy community," he says. But Looney, and some
members of the Board of Aldermen, see the letter as "symptomatic
of his overall approach of being divisive and harsh rather than
Looney claims that the mayor’s inability to work with others
has cost him the support of many of his former Democratic party
allies. "There’s been a sort of estrangement and alienation
from a number of people in the community, and obviously the mayor’s
trying to turn that into an advantage by saying that the fact
that he doesn’t have a relationship with x, y, and z is because
of his own actions," he says. But in Looney’s eyes, the
mayor’s break from the Democratic Party’s machine does not signal
a reformed City Hall; rather, the mayor has created his own system
of patronage-a machine that revolves less around the party and
more around those individuals who give to the mayor’s campaign.
Looney pledges to dismantle that machine. "My approach to
government will be inclusive, participatory, responsive to segments
of the community," he says. "It will signal an end
to factionalism, and a unified party and administration."

In the last year, some local Democrats have noticed a change
in the mayor. " He became more charismatic, more popular,
more responsive," Alderman Julio Gonzalez said last fall,
before he joined the mayor’s campaign. "I really feel there
has been a change in the tone of the administration."
Gonzalez is not alone in his newfound enthusiasm for the DeStefano
administration. The race for the nomination has not only split
the Democratic party, but has also strengthened the convictions
of each side. Local leaders who had previously shown lukewarm
support for the mayor are preparing to actively campaign for
him. Bill Dyson, who represents New Haven in the Connecticut
Assembly, will support DeStefano because, in his opinion, the
Looney camp has offered no agenda, while DeStefano has "made
a vast improvement."
The mayor is hesitant to say that he has changed significantly
in the last year-that would be an admission that his first six
years were much less productive and energetic. But he knows he
learned something from Jim Newton’s strong showing in 1999: "Two
years ago voters sent me a message [that] they were concerned
with city government," he says of the last election.
Gonzalez and Dyson attribute the mayor’s new attitude to his
rift with Democratic leaders like Balletto. As Dyson explains,
"[DeStefano] is slowly but surely surrounding himself with
people that he trusts." Indeed, the people surrounding each
candidate have become as much of an issue in this campaign as
the candidates themselves. During his first six years in office,
it seemed that DeStefano could not avoid scandal. He managed
to come through nearly unscathed each time, while members of
his administration took the fall. In the process, the look of
City Hall has changed. Chief Administrative Officer Jim Horan
had not lived in New Haven prior to working for the mayor. The
head of economic development is no longer a veteran of New Haven
politics, but a young graduate of Yale Law School named Henry
Supporters seem to think DeStefano has broken free of his debts
to the party that got him the job. "When you first get elected
there’s a tendency to bring in the people who brought you to
the dance," DeStefano admits. But the general feeling in
New Haven is that the Democratic Party does not work the way
it used to. If the mayor can convince New Haven that he is the
one responsible for turning an oligarchy into a meritocracy,
he will be mayor again next year.

With people like Balletto seemingly on his side, Looney may
find it difficult to distance himself from the traditional ways
of the Democratic machine. "Rewarding friends in the city
is something [the old party bosses] did well," says Robin
Kroogman, an alderwoman who will likely support Looney. She faults
the mayor for hiring staffers from outside the city, pointing
to Fernandez, Horan, and parks director Robert Levine, who moved
from Virginia to New Haven to take the job.
DeStefano’s supporters believe that the mayor’s administration
has found the necessary balance between the reformer, grassroots
liberals, and the traditional, Party-oriented Democrats. "On
the one hand, the mayor gets criticized for working with Party
regulars; on the other, he’s criticized for not working with
them," Nemerson says. "If you study urban politics
in America, all of the successful mayors . . . present themselves
as reformers who are going to do things in a market-based way,
while cutting as many deals as they can." While it might
not seem right, patronage always has and probably always will
play some role in New Haven politics. It’s a part of the DeStefano
administration, but it would surely be a part of the Looney administration
as well.
In fact, the Looney team features many former players from DeStefano’s
City Hall. For example, Patti Cofrancesco, formerly a top city
lawyer, was fired by the mayor after signing off on questionable
city loans to another city employee, Andrea Jackson-Brooks. Now,
Jackson-Brooks is on the Board of Aldermen, Cofrancesco practices
law in New Haven, and both are expected to support Looney.
Why would Looney, who has usually been known as a reformer, join
the Party team? His first job in city government was as aide
to Mayor Frank Logue, a non-machine candidate in the 1970s. Martin
Looney has had his eye on City Hall for a long time, and the
rift in local Democratic leadership might give him the best opportunity
anyone has had to unseat DeStefano. "[Looney] is a good
guy with a clean record who’s right on state issues," Gonzalez
says. "I just don’t see how he could govern without appeasing
that [Party] base."

Mayor DeStefano thinks voters don’t care about political maneuvering-they
want the soccer fields mowed and the schools improved. "When
you’ve got an incumbent, [the voters] are going to look and say,
‘Am I satisfied or not?’" In his opinion, the people of
New Haven are better off now than they were before he became
mayor. "There’s no doubt that New Haven is a more confident
place than it was a year ago."
The mayor is right about most voters: They don’t care about politics,
who’s running whose campaign, and who’s supporting whom. They
will decide the election based on how their lives are right now,
and they care about schools, parks, and policing. But they also
want a City Hall free of debts to political bosses and corporate
donors-something neither DeStefano nor Looney can promise.


Michael Gerber, a senior in Ezra Stiles
College, is a contributing editor of

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