Is Rudy Picking on a Weakling?

It may turn out to be a red herring for the ages, but Thursday afternoon brought a report – citing a single, unnamed source – that Rudy Giuliani would within the next 48 hours announce his candidacy for the U.S. Senate seat now held by Kirsten Gillibrand.

Let’s assume the news is true.

If he really is running for the Senate, then Rudy ought to first be applauded for making an unexpectedly shrewd political calculation. All year, he’s flirted (very unconvincingly) with a gubernatorial bid. His interest, it’s been clear, has been directly linked to David Paterson’s prospects of being the Democratic nominee – which are (and have been for months) non-existent.

Meanwhile, he’s shown absolutely no outward interest in the Senate race – even as it’s become clear that Gillibrand, an appointed incumbent who is still struggling to win New Yorkers over, would be a much riper target than Andrew Cuomo, the mega-popular attorney general who’s set to supplant Paterson as the Democrats’ gubernatorial standard-bearer.

In fact, he’s gone out of his way this summer and fall to shoot down suggestion that he run for the Senate – a far cry from the maybe-I-will-maybe-I-won’t gubernatorial coyness.

So word of his apparent interest in the Senate on Thursday really did come out of nowhere (something that immediately raised suspicions that Rudy’s camp was floating the Senate story to soften the blow from a New York Times report earlier on Thursday that he had finally decided to officially withdraw his name from the gubernatorial mix).

But the Senate race really is an excellent fit for Rudy. Even in the wake of his gruesome 2008 White House campaign collapsed, it’s been apparent that he hungers to secure a high-profile elected office. But at 65 years old, he’s running out of chances – meaning that 2010 really would have to be his year to get back in the game, if he’s ever going to.

And that means either running for governor or for the Senate. And with Cuomo, by far the most popular politician in New York, regularly besting Rudy by double-digits in gubernatorial trial heats, that leaves the Senate race as his only ’10 option.

Earlier this year, a campaign against Gillibrand wasn’t very attractive for Rudy, or for any Republican. The circumstances of Gillibrand’s January appointment by Paterson were hardly ideal, but she was attractive, intelligent, knew how to raise money, and had cultivated a moderate, upstate-friendly reputation that would surely help her in a general election. Plus, she had the White House (and Chuck Schumer) running interference to clear the Democratic primary field for her.

It stood to reason that Gillibrand’s poll numbers would be very healthy by the end of 2009 and that she’d win with ease in ’10. In the post-Gingrich era, don’t forget, Republicans haven’t come within ten points of winning a Senate race in New York.

But the Gillibrand race looks far different now. For one thing, she’s utterly failed to connect with New Yorkers. In the latest Siena poll, her favorable rating is a lukewarm 34 percent, and only 33 percent of voters rate her performance as excellent or good; 45 percent rate her work fair or poor. In a hypothetical match-up against George Pataki (who until now was seen as a more likely Senate candidate than Rudy), she’s locked in a dead heat.

Rudy, on the other hand, has a 62 percent favorable rating. He’s roughly as popular statewide as Schumer is (although their support comes from different areas), and in a well-timed Marist poll released Thursday, he leads Gillibrand in a trial heat by 14 points – 54 to 40 percent.

What’s even more significant for Rudy is that the ’10 political climate in New York figures to be as favorable for a Republican candidate for federal office as it has been in nearly two decades – since the 1994 G.O.P. revolution. For the last 15 years, Democrats in New York and other blue states have gotten fat off the G.O.P.’s domination of Washington, with voters immediately rejecting Republican candidates solely on the basis of their party label.

But that won’t be the case next year. With Democrats running the show in D.C., blue state swing voters will at least be open to listening to Republican candidates. (This is how Republicans just won the governorship in New Jersey, where the Democrats’ run-against-the-Washington-Republicans strategy failed for the first time in years.)

In a year like 2006 or 2008, Giuliani’s strong favorable numbers (and Gillibrand’s weak ones) wouldn’t have counted for much; he still probably would have lost to her in New York, with voters blinded by their anti-G.O.P. rage. But they will count for a lot in 2010. Giuliani absolutely can defeat Gillibrand. It wouldn’t be unreasonable to make him the favorite if he does jump in.

The strong prospect of a Giuliani victory raises two questions: (1) How will Democrats react? and (2) What will Rudy do if he’s elected?

On the first question, the most likely scenario is that the White House (and Schumer) will double down on their efforts to fortify Gillibrand, leaning on Democrats in the state and around the country to raise gobs of cash for her and making sure that no opportunity-sniffing Democrat gets any last-minute ideas about challenging her in next September’s primary. Gillibrand has been their candidate since January; it’s not like they’re going to bail on her now.

But this may look very foolish next November. She seemed like a promising candidate back in January, but Gillibrand has proven herself to be awkward and inept as a statewide politician. Her shift from the center to the left (to head off a primary challenge) was awkward and her communication skills are dreadful. Forget swing voters; Democrats aren’t even close to sold on her: the Siena poll had her racking up only 47 percent against Jonathan Tasini, her hapless token primary opponent.

Giuliani’s emergence should prompt Democrats to seriously reconsider the wisdom of nominating Gillibrand. Not that it will, of course. Not only is the White House wedded to her, there just aren’t any obvious Democratic heavyweights who could jump in at this point and take her on. Cuomo would have the stature to do it, but he’s busy performing a rescue mission for the party in the gubernatorial race. There’s no clear alternative to Gillibrand for Democrats, so they’re probably stuck with her.

The second question – about what a Senator Rudy might do – is more interesting. Thursday’s report suggested that he’d turn around and run for president in 2012, and that he probably wouldn’t seek re-election in 2012. (The ’10 race is actually a special election to fill the two remaining years of the term Hillary Clinton was elected to in 2006.)

There’s plenty of superficial logic to this: Rudy obviously wants to be president and even after last year’s campaign, he’s still trying – hard – to win over the national party’s conservative base. And since his ’08 campaign didn’t end well, Rudy would need to post a comeback victory for some other office before setting out to run for the White House again. So why not run for the Senate?

But the idea of Rudy running for the G.O.P. nomination again is also baffling. He spent $57 million on his ’08 campaign – and won one delegate. That’s the worst dollars-for-delegates ratio in history.

Second-chance White House candidates usually build on respectable showings, but Rudy’s campaign was a complete and total train wreck – right up there with John Connolly’s in 1980 and Phil Gramm’s in 1996. No one ever talked about them running again, and for good reason. Why on earth would a follow-up campaign by Rudy fare any better than the first one?

But maybe Rudy doesn’t see it this way. He wouldn’t be the first person blinded by ego and ambition. And even if he does understand that he won’t be president, that doesn’t mean the Senate would be miserable for him. What he’d lack in seniority, he’d make up for in star power. He’s have an opportunity to be the public face of the Senate G.O.P. – well-attended press conferences, regular appearances on Sunday morning news shows, and so on. It would give him new stature and relevance. He can’t milk the “America’s Mayor” thing forever, right? Is Rudy Picking on a Weakling?