Thompson's Options: Senator (Risky), Comptroller (Safer), Mayor (TK)

On Election Night, I called Bill Thompson the Christie Whitman of New York politics, since his startlingly narrow, 4.6-point loss to Mayor Bloomberg represented perhaps the biggest near-miss shocker since a then-unknown Whitman came within two points of unseating Bill Bradley in 1990.

And now he's doing exactly what Whitman did after that election: figuring out how to parlay it into another campaign.

In Whitman's case, that meant waiting for the next statewide contest in New Jersey, the 1993 governor's race—which she ended up winning in a squeaker over Democratic incumbent Jim Florio. But Thompson, who admitted this week that there's "a very good chance" he'll run for office again, won't have to wait that long.

There are three obvious options on his plate: a campaign for Kirsten Gillibrand's Senate seat, a run for state comptroller, or another mayoral bid in 2013. There are pros and cons to each choice.

A Senate race would be a high-stakes gamble. The payoff would be enormous: Especially if Rudy Giuliani (or George Pataki, for that matter) doesn't seek the Republican nomination, victory in next September's Democratic primary would be tantamount to winning the seat in November.

So Thompson would have to knock off Gillibrand—an appointed incumbent with poor communication skills who has failed to make much of an impression on voters and who remains distrusted by many liberal activists—and a spot in the U.S. Senate would probably be his. He'd be a national figure; not bad for a guy who was ridiculed by the New York press (not to mention many of his fellow Democrats) for almost all of 2009.

For now, there's been no polling on a potential Gillibrand-Thompson race. But it's obvious she's vulnerable. A Siena poll in mid-November showed her failing to break 50 percent against the largely anonymous Jonathan Tasini. Thompson could run against her from the left, playing up the conservative positions Gillibrand took as an upstate congresswoman (and her shiftiness in throwing all of those positions out when she was appointed to the Senate). He could also paint her as the insiders' candidate—hand-chosen by an unpopular governor and propped up by Chuck Schumer and state and national party leaders.

That said, Thompson would still be the underdog, mainly because Gillibrand, who already has more than $5 million in the bank, would have a lot more money to spend. Plus, more than half of all voters statewide still don't know who he is, according to the Siena poll. To suburban and upstate voters, he might be pigeonholed as just another New York City politician.

There would also, presumably, be enormous pressure from the White House (and Schumer) for Democrats to rally around Gillibrand, the incumbent. But this might not mean much to Thompson, who was humiliated by the White House during the mayoral race—and still almost won. (This also might give the White House pause about leaning too heavily on Thompson this time around.) Plus, if Giuliani and Pataki do opt out, the seat will be fairly safe for the Democrats, making it less urgent that they avoid a costly and divisive primary.

The downside for Thompson is that a loss would kill all of the career momentum that his near-miss last month generated. When it looked like he was going to lose to Michael Bloomberg by 15 points, no one was seriously talking about Thompson's future political prospects. By overachieving, he was able to change that. But now the pressure is on: If he can't parlay his new status into a victory, he'll be written off all over again.

This is why the state comptroller's race would be a safer (if lower-yield) bet for Thompson. As with the Senate race, he'd have to oppose an unelected incumbent in the Democratic primary—Tom DiNapoli, who was appointed by the Legislature in 2007. But DiNapoli is more vulnerable. His poll numbers are as shaky as Gillibrand's, and he isn't fortified by the establishment strong-arming from which she benefits.

In fact, there is some tension between Andrew Cuomo, the hugely popular attorney general who figures to head the Democrats' 2010 ticket, and DiNapoli, fueling talk that Cuomo would prefer to run with a different candidate for comptroller. An alliance with Thompson might be tempting for him: They get along, Thompson is more than qualified for the job, and his presence would ensure that at least one African-American is on the ticket.

Granted, a primary campaign against DiNapoli wouldn't be a cakewalk for Thompson. That same Siena poll showed them tied at 31 percent. But, especially if he were to team up with Cuomo, Thompson would have better odds than he would against Gillibrand.

The payoff would be somewhat more modest. He'd be able to use the post to raise money, but being comptroller wouldn't do much for his statewide visibility (to say nothing of a national reputation). Still, a stint as comptroller could give Thompson more credibility for a future run for a higher-profile office.

And there's Option Three—another run for mayor in 2013. This, some who know him seem to believe, is the job Thompson wants most.

Since it's four years away, there is a school of thought that he could run for the Senate or state comptroller next year, win, and then use that office as a launching-pad for a mayoral campaign. Realistically, this would be more practical with the comptroller's office than a U.S. Senate seat, which is a prize in itself. Of course, he if were to run for either job and lose, his mayoral stock—which is higher right now than at any point in this year's campaign—would take a hit, possibly a lethal one.

But. If Thompson avoids any more campaigns between now and '13, it would hurt his visibility. His surprising showing in this year's election could be all but forgotten by then and might not benefit him much with the press or the public. Even though he gave Bloomberg a scare, there are still doubts about Thompson's strength as a candidate—and suggestions that his showing was simply a function of his Democratic label and of Bloomberg fatigue. An election win between now and '13 would shift this thinking; otherwise, he might still face a skepticism hurdle in a follow-up bid.

Thompson said this week that he'll decide soon whether to run for office next year. To be sure, going after Gillibrand or DiNapoli would be a risky venture. But the old cliché about striking while the iron is hot comes to mind. Thompson's best bet is probably to capitalize on his mayoral near-miss while people are still impressed by it.