As waiters serving lobster and shrimp return to the kitchen at Valbella in Riverside, Conn., John DeStefano begins to explain why he wants to be governor in Connecticut.

“New Haven has done one thing to me,” DeStefano tells a group of potential supporters at the fancy Italian restaurant. “It’s made me an optimist.”

DeStefano relates an anecdote about a first-time homeowner who, he explains, did not know how to nail a picture to a wall because she had spent her entire life living in public housing made of concrete. He talks of attending a funeral for a six-month-old baby who was shot and killed only weeks after he became mayor — and how since then, the city’s murder rate has plummeted. He speaks of a restructured police department, a decline in the high school dropout rate by nearly half, and the fact that over half of Connecticut’s biotech firms are in New Haven.

Serving over a decade as mayor of the Elm City, DeStefano tells the crowd of about 25, has taught him that “with the right ideas and the right leadership, you can build better places.” So, the 49-year-old Democrat continues, he wants to change Connecticut, too. He calls for a “Marshall Plan” for the state’s transportation system, a renewed focus on job creation, and a pledge that all Connecticut children will be ready for kindergarten.

Almost two years still remain until Connecticut Democrats will choose a nominee for the 2006 governor’s race, but nearly every day, DeStefano is making this pitch. As his party begins to look at a potentially crowded field of candidates looking to become the first Democrat to occupy the governor’s mansion since 1991, the mayor is telling the party’s decision-makers, opinion leaders, fundraisers and anyone else willing to pay attention that he wants to change Connecticut just like he says he changed New Haven.

But at Valbella, most of the locals listening to DeStefano, even at this $1,000-a-plate fundraiser, have only just been introduced to him. As DeStefano works the room in the restaurant, many of those meeting him for the first time echo local architect Mark Strazza, who says he is impressed with the mayor’s pitch about New Haven but just does not “think it registers with a lot of people.”

For DeStefano, the Valbella crowd illustrates both the opportunities and the challenges he faces as he embarks on his first campaign for statewide office. The mayor argues that by the time voters begin paying attention, he will already have the three things he says a winning campaign needs: a powerful message, an effective political operation and the money to run all across Connecticut. But first, DeStefano has a lot of introducing to do.

Moving outward

Without traffic, Riverside is only a 50-minute drive down Interstate 95 from New Haven. But in many ways, it is much farther removed from the Elm City. Compared to the average New Haven family, a Riverside family is likely to be about three times as wealthy. About half of New Haven’s population is black or Hispanic; Riverside is about 90 percent white.

But if DeStefano is to run a competitive race, he will have to find a way to attract voters in towns like Riverside, Putnam and Torrington, places different in many ways from the city where DeStefano has lived and has worked since he was born. As a result, even while the field of candidates is still uncertain, this stage in the race represents a key time for the six-term New Haven mayor.

Roy Occhiogrosso, a top Democratic strategist in Connecticut who managed Bill Curry’s unsuccessful race against recently resigned Gov. John Rowland in 2002, said a candidate who lacks statewide name recognition must demonstrate his credibility early.

“The downside is that if you are the mayor of Stamford or New Haven, you are really well known there, but outside of that, you are not,” Occhiogrosso said. “But that’s a downside only if you don’t have the money or energy to run a strong campaign throughout the state.”

DeStefano, of course, is not venturing outside of New Haven for the first time. He has long been one of the most visible mayors in Connecticut, most recently as the chair of a commission focused on reforming the state’s tax system and reducing sprawl. DeStefano can even boast of his experience in Washington, D.C., having served as the president of the National League of Cities last year.

But in Connecticut’s recent history, no mayor has made a direct leap from a City Hall to the governor’s mansion. DeStefano’s fundraising so far serves as an example of the challenge he faces in extending beyond his base. Today, DeStefano will announce at an event in New Haven that he has raised over $1 million. But of the $683,000 his campaign had reported in contributions at the last campaign filing deadline in June, over half of the money came from New Haven County.

Still, DeStefano says he is not worried. His campaign has divided the state into about 20 “affinity groups” of towns, working on establishing an organization in every region of the state. The mayor has also set ambitious goals for fundraising that will require him to attract donors from across the state, arguing that a successful candidate will need to raise $7 million by November 2006 — far more than any Connecticut Democrat has ever raised before.

Maintaining a winning record?

In Riverside and at his other events across the state, DeStefano’s campaign hands out mock baseball cards with the mayor’s face on it. On the back are “key statistics” from DeStefano’s tenure as mayor: crime cut by 44 percent under his watch, 20 new schools built, a $12.5 million budget surplus overall.

But the year-by-year statistics on the card stop at 2002. In 2003, for the first time in a decade, the crime rate inched up by one percent. After years of balanced budgets and tax cuts, DeStefano has pushed through three consecutive property tax rate increases. The mayor’s school-building has come under fire by some critics who argue that it has done little to improve the quality of education.

Many of the New Haven’s successes and failures are due to factors well outside DeStefano’s control — decisions in Hartford, the national economy, long-term demographic shifts — yet credit and blame often fall on the mayor. And even as DeStefano travels the state, he faces the constant stress of his current job, not to mention a reelection campaign in 2005.

Three candidates have declared their interest in challenging DeStefano for mayor next year — former aldermen Tom Holahan ’63 GRD ’72, Willie Greene and an ex-city spokesman, Gary Jenkins. DeStefano aides said the mayor welcomes a campaign that allows for a discussion of the city’s issues, but all three are considered long-shot candidates. Yet at the same time, the candidates are pointing to DeStefano’s statewide ambitions as a sign that he is becoming out of touch with the local community.

Ward 4 Alderwoman Andrea Jackson-Brooks, a former DeStefano aide who opposed the mayor in his closest reelection fight in 2001, said while the mayor can take some credit for helping to redevelop the Elm City, residents are worried that he has lost focus.

“I hear it everyday,” Jackson-Brooks said. “People are very concerned that he’s not as accessible as he was, he’s not as visible as he was, he’s not as knowledgeable as he was.”

But DeStefano argues that the division between being a mayor and being a gubernatorial candidate is not so large. Being a good mayor, he has said, is necessary to running a successful statewide race. At the same time, he explains that his campaign for governor is focused directly on the issues that will make New Haven a better place.

“I think folks will worry if the dropout rate goes up, crime dramatically increases, if neighborhoods are not safe,” DeStefano said in an interview in his office. “That’s the point when I’ll be concerned.”

At the same time, DeStefano must ensure that he is associated with policies beyond those directed at helping New Haven. The statewide issue he has become most identified with, property tax reform, would likely aid the largest cities, even if DeStefano argues it is a key means of fighting sprawl and overdevelopment across Connecticut.

Service Employees International Union Local 1199 President Jerry Brown, a prominent Connecticut Democrat who has worked closely with DeStefano on organizing drives at Yale-New Haven Hospital, explained that the mayor must demonstrate that he understands the problems Connecticut faces outside its central cities.

“It’s getting outside the image of ‘OK, he wants to become the governor because he wants New Haven and Hartford and Bridgeport and Waterbury to get more resources,'” Brown said.

The 500-pound gorilla and other obstacles

At this point in the race — with 35 months until the August 2006 primary and only a handful of voters even aware of who is running — there are few objective measures of how well a candidate is doing. No polls have been taken and virtually no endorsements have been made. The sole rough estimate of how a candidate is doing is the quarterly financial statement.

If money is the measure of a campaign in its early stages, then DeStefano, Malloy and Bysiewicz can all claim that they have demonstrated their credibility as candidates. DeStefano and Malloy will likely both have raised over $1 million by the end of the month, and Bysiewicz has gathered about as much, even though her “exploratory committee” can only accept donations up to $250 rather than the typical $2,500. As impressively, these candidates have done so while preparing for a race that is on the backburner for even many Democratic activists and remains entirely off the radar screen for the average Connecticut voter.

Yet Bill Curry, the two-time Democratic nominee for governor, said the candidates may also run into the limits of what they can do this early in a campaign.

“You can raise your visibility, but very little. You can organize, but it isn’t really a three-year organizational task. And you can raise money. But in each case — certainly for the mayors — there is a certain amount of money that the people they do business with give them, and that will be the case until we change the system,” said Curry, who still has not made a decision whether he will run for governor again.

Whether or not DeStefano’s criss-crossing of the state today will matter in two years may also depend on who else enters the race. The state’s senior senator, Chris Dodd, has long been thought to be interested in running for governor, and several Democrats said in interviews they thought he might at least consider a campaign. A more likely candidate is Connecticut Attorney General Richard Blumenthal LAW ’73, who has been linked to possible gubernatorial runs for over a decade.

“He’s a 500-pound gorilla. In Connecticut politics, people have been waiting a long time for him to run,” said John Droney, a well-connected Democrat who co-chaired Bill Clinton’s Connecticut campaign in 1996.

Blumenthal said in an interview last week that he will not make a decision until after November’s elections. Until then, he said, he is focused on the presidential race and his current job in Hartford. Although he said he finds many aspects of the governor’s office attractive and believes a Democrat would have a good chance of winning the general election in 2006, he said he still has enough time to continue to consider his options.

“It’s a tremendous challenge and opportunity to do a lot of good for people,” Blumenthal said. “[But] my focus right now is on being the best possible attorney general I can be.”

In interviews, DeStefano, Bysiewicz and Malloy all said they fully intend to run for governor, and that they are not waiting for Blumenthal to make a decision. Beyond Dodd and Blumenthal, others could enter the fray, too. State Treasurer Denise Nappier, Lt. Gov. Kevin Sullivan and Curry represent only a partial list of possible candidates.

Until November, most Democrats, like Blumenthal, will still be focused on the presidential campaign. After then, several Democrats said in interviews, attention is likely to turn towards the governor’s race — not least because any Democratic nominee may face a formidable opponent.

This spring, when DeStefano announced his candidacy, Rowland was facing a possible impeachment trial over allegations of corruption. In July, he resigned and was replaced by Lt. Gov. Jodi Rell, who has since earned some of the highest approval ratings in Connecticut history. While Rell has not yet announced her plans for 2006, Democrats said they are particularly concerned with choosing the ideal nominee because of the possibility of facing a popular incumbent.

“People can’t take her lightly,” said John Olsen, the president of the Connecticut AFL-CIO and a major figure in the state’s Democratic Party. “She has the approval rating now because she’s not John Rowland, but I think she’s working very hard at it.”

An uphill battle

In interviews, several people active in the Connecticut Democratic Party from across the state said they believe that DeStefano has a chance at achieving the nomination. But they nearly uniformly agreed that DeStefano would face an uphill battle.

If Blumenthal enters the race, several said, the attorney general would be the heavy favorite. Wealthy, highly visible and one of the most popular public figures in the state, Blumenthal would likely draw significant support from both the Democratic Party establishment and rank-and-file voters. But even if Blumenthal stays out, Bysiewicz and Malloy, along with anyone else who decided to enter the fray, would pose a formidable obstacle for DeStefano, Democrats said.

Malloy has the advantage of having a base in Fairfield County, one of the wealthiest areas in the country. At an event in New Haven in late August, Malloy explained that his ability to compete in a general election helps underscore why he is a strong contender.

“I think I will have the broadest appeal to Democratic voters who really see this as an opportunity, if we play our cards right, to get a Democrat elected,” Malloy said at the event.

Bysiewicz, for her part, has run successfully on two statewide tickets before. The secretary of state’s office may not be a very high-profile position, but Bysiewicz still has the advantage of having already appeared on ballots in all 169 Connecticut cities and towns — an experience neither DeStefano nor Malloy has.

“[Bysiewicz] is not as well-known as Blumenthal, but she’s much better known than DeStefano,” University of Connecticut pollster and political science professor Ken Dautrich said.

At the same time, DeStefano has clear executive experience and a reputation, as SEIU’s Jerry Brown said, as a “policy wonk.” He has a clear regional base in an area of the state that is important in a Democratic primary. And he can point to a distinct record in New Haven, as he does in Riverside and across the state.

For now, though, only a few people are listening. Whether DeStefano can convince them that his tenure in the Elm City shows he can make the uncharacteristic jump from mayor to governor could go a long way in determining if he appears at the top of the Democratic ticket in 2006.

“This is not a race that’s going to be won this week or next month or even next year,” DeStefano said. “At the end of the day, what I’ve learned in New Haven is that it is basically up to you.”

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