William Thompson Jr., New York City's Comptroller, may be running for Mayor. He has certainly impressed many people with his quest for accountability with the Snapple deal, and we ask, should he be Mayor?

Will Bill?
Bill Thompson is mild-mannered, relatively unknown, and not sure he wants to run. So how is it that the city comptroller may be the next mayor?By Greg Sargent [New York Magazine, May 3, 2004 issue]

William Thompson, the city comptroller, was camped out at his favorite place for talking politics, a quiet corner table at the River Café, just under the Brooklyn Bridge. He was trying to convince me that Michael Bloomberg is vulnerable in 2005 to a challenge from . . . William Thompson.

"Does Bloomberg have a base?" Thompson wondered out loud. "There are parts of Manhattan that are comfortable with Mike, but that's about it. I don't think he has an identifiable base anywhere that's his. Is there a vision for the future of New York City? I haven't seen one. Where is this city going to be ten years down the road?"

The talk turned to the mayor's leadership, or lack of it, and Thompson, naturally, continued his assault. He started micro: On Bloomberg's refusal to go after the MTA over fare hikes, "there was no leadership from the mayor," he said. Then he went macro: "Has the president been fair to New York City after September 11? The answer is no. Mike looks at things as, 'If I don't make the president mad today, I'll have a shot at something tomorrow.' You'd like to see the mayor fight for the city.

"As the mayor, your opinion counts," Thompson went on. "You have an important national voice. Where is it?" He shook his head. "I mean, Mike doesn't get it."

You may have heard that a handful of Democrats out there want Mike Bloomberg's job. There's Gifford Miller, the precocious 33-year-old City Council speaker who couldn't disguise his mayoral ambitions if he wanted to; Fernando Ferrer, the Puerto Rican former Bronx borough president who's been running for mayor on and off since the mid-nineties; and Brooklyn Representative Anthony Weiner in the self-assigned role of scrappy Jewish outer-borough insurgent.

His low Q rating notwithstanding, Thompson is the would-be mayor with the best shot at beating Bloomberg.

Then there's Thompson. Despite the fact that he holds the city's third most powerful government office, the 50-year-old, bespectacled accountant-in-chief is not exactly a boldface name. To date, his greatest political coup has been taking on the mayor over the Snapple-in-the-schools deal, a battle that's drawn its share of attention, but not very much of it for the person who's waging it. But even if you've never heard of the man, here's why you ought to know about him: His low Q rating notwithstanding, he's the would-be mayor with the best shot at beating Bloomberg.

Do the electoral math. in the Democratic primary, Thompson starts out with perhaps the largest base-African-Americans. What's more, as the only mayoral wannabe who's won citywide office, he has shown he's got something that his Democratic rivals have yet to display: crossover appeal. Sure, Ferrer has a fat lead in the primary polls and begins with a base of Latinos that rivals Thompson's core black support. But Thompson may prove able to assemble a broader coalition than Ferrer, because he's likely to enjoy broader appeal among whites. While Ferrer won over some white liberals in the 2001 Democratic primary, it was largely due to their disenchantment with Mark Green. Thompson, because of his moderate manner and Wall Street experience (he was an investment banker in the early nineties), may attract a broader spectrum of white voters-liberals, but also outer-borough Catholics and Jews. Miller, meanwhile, is untested among those outer-borough whites-voters who would be key to a primary victory for him. If Thompson holds his base and picks up just enough moderate Jews and Catholics and liberals from the Upper West Side and brownstone Brooklyn, he could win a primary. It's worth noting that Thompson did reasonably well among whites in Manhattan and Brooklyn in the 2001 comptroller's race, against a white opponent.

In the general election, Thompson also has advantages against Bloomberg that his rivals lack. He'd be able to assemble a coalition of blacks, Latinos, and labor, yet his acceptability to outer-borough whites, who generally dislike the mayor, might induce some of them to sit out the election. Thompson would also get a boost from a growing class of black homeowners in Queens and Brooklyn. And in an era when "career politician" is a lethal epithet (ask Mark Green), Thompson's detour through Wall Street might blunt efforts by Bloomberg to paint him as a lifelong pol.

"If you're asking who has the most strength against Bloomberg, there's no question it's Thompson," says Bloomberg backer Ed Koch. "He has a black base to start with, he's been a good city comptroller, and he has lots of friends among the other ethnic groups."

Although Thompson has differed with Bloomberg on a number of fronts-budget cuts, firehouse closings, social promotion in schools, Snapplegate-his chief line of attack against the mayor seems, for now, to be about style.

"The argument against Bloomberg that works is one that talks about inspired leadership in the city," Thompson says. "It's one that talks about some of the comments that Mike makes-'There's nobody who works at minimum wage in New York'-that clearly show he doesn't fully understand the city he represents. If I didn't think that I could be a better leader than the mayor, then I wouldn't consider running."

The son of a powerful Brooklyn judge, Thompson built his career mostly out of public view. Starting in the early seventies, he rose through the Brooklyn political machine, from congressional aide to deputy borough president, did his Wall Street tour, then headed the Board of Education, before notching his 2001 surprise victory as comptroller, his first run at elected office.

Along the way, he built relationships with county leaders, powerful Williamsburg rabbis, labor kingpins, and business and real-estate executives. Those relationships, he says, helped him develop the kind of broad-based understanding of the city that he says Bloomberg lacks. The mayor's aides, for their part, say Thompson's broadside lacks substance. "If Billy wants to run for mayor, he has to tell us what he would do differently," says Bloomberg spokesman William Cunningham. "Instead, he gives us a cheap political attack and goes on his merry way."

Thompson's primary rivals, meanwhile, argue that his political math is fuzzy. Ferrer supporters say that their guy is far better known; there's no way the virtually unknown Thompson can compete. Miller backers say a Thompson candidacy helps them; it will split the minority vote, and the white vote will put them over the top.

Just about everyone is aware of Thompson's lackluster stump style. After Thompson's remarks at a recent labor dinner were met with perfunctory applause, Miller gave a rousing speech that, his preppy aura notwithstanding, had the mostly minority audience whooping. Thompson could easily become another Carl McCall-liked by insiders but unable to rev up voters.

Incumbency is formidable enough when it isn't backed by $100 million, and many are convinced that in the end, Thompson will prove far too cautious to brave the 2005 contest. Why give up a cushy comptroller's gig and risk a crowded primary, much less a general election against a $4 billion incumbent? Thompson, they say, will run for easy reelection and take his shot at City Hall in 2009.

Thompson is also wary of a repeat of 2001, when revenge-minded Ferrer backers withheld support from Mark Green after the primary. Thompson has privately raised these concerns with Ferrer. "I've said to Freddy that we all may wind up in this race," Thompson says. "It would mean that both of us have to walk on eggshells. We have to be careful not to alienate the other person's constituency."

Thompson advisers concede that Bloomberg has begun to connect with voters-an April 23 Times poll put the mayor's approval rating at 38 percent, up from 24 percent a year ago. If the mayor's popularity keeps rising, Thompson won't run. But if Bloomberg's support next fall is no stronger than it is today-the poll also said 64 percent of New Yorkers want a new mayor-then there's little doubt Thompson will join the race. After all, not running might allow another Dem to win, forcing Thompson to put off a mayoral run until 2013.

Sources say Thompson adviser Hank Sheinkopf is interviewing pollsters and will be polling by May. So what are the odds of a Thompson run? "It's 60-40," Thompson says. "If I think I can beat him, I'll go."

And if he had to decide today? He doesn't miss a beat: "Yes."