The Senate Super Bowl of ‘06: Rudy vs. Hillary

The word around New York is that our former mayor, Rudy Giuliani, has decided to challenge Sen. Hillary Rodham Clinton when she seeks reelection in 2006 -- a matchup we almost saw in 2002 before he withdrew for personal reasons. Giuliani won’t confirm or deny it (as recently as Friday he told radio host Don Imus he hadn’t made up his mind), but two well-placed GOP insiders say it’s “basically a done deal.”

This would be the Super Bowl of Senate races and a dramatic “wild card” lead-in to the 2008 presidential election. Only one of the principals could advance to the next level.

For Giuliani, challenging Clinton is a necessary step if he hopes to be a national GOP player. He could, if he chose, run for governor in 2006, but that wouldn’t do him much good on the national stage. He would still be a pro-gay, pro-choice “Rockefeller Republican.”

But Senator Giuliani would be a different matter. He would have slain the dragon, and slaying the dragon would bestow upon him exalted status. Major points of difference with the GOP’s core constituencies -- like the sanctity of life (abortion) and the evolution of mankind (stem cell research) -- would become much less disqualifying.

Red State Republicans -- those from the GOP stronghold states -- could learn to love Rudy in a New York minute if he beat Hillary.


And make no mistake about it, Giuliani wants them to love him. He wants to play on the national GOP stage. His leadership in the city after the World Trade Center massacre made him a national hero, and he has leveraged that status skillfully these last two years. He has published a bestselling book, established a lucrative consulting practice, built a strong political bridge to the Bush administration and emerged as a huge GOP campaign asset. Indeed, after President Bush, Giuliani was widely seen as the most productive Republican campaigner of the 2002 midterm election cycle.

Like most political observers, Giuliani assumes that President Bush will be reelected in 2004, and he intends to campaign hard on his behalf and on behalf of the GOP’s efforts to gain more seats in Congress. This will take him down South, a lot, where five Democratic Senate seats are up for grabs because of retirements.

The combined account of his 2002 and 2004 political chits should enable Giuliani to raise a ton of money for a campaign against Clinton in 2006 and to enlist an army of volunteers. The GOP faithful, from coast to coast, will be rooting him on as if he was Ronald Reagan reincarnate. If he unseats Hillary Clinton (which will difficult, but certainly not impossible), he would instantly become an acceptable vice presidential nominee choice, particularly if Florida Gov. Jeb Bush (by way of disclosure, he is my first cousin) heads the 2008 GOP ticket.

As for Clinton, the looming Giuliani candidacy complicates her calculations regarding 2004. Clearly, she will need to stay focused on New York. But if her party comes calling, she may wind up being a vice presidential nominee on a Howard Dean or Richard Gephardt ticket. A national race might elevate her stature -- but being part of a losing ticket can tarnish one’s brand and diminish future prospects. She probably will protect her base first and worry about the national pieces later.

Regarding 2006, the only acceptable result for Clinton is victory. By then, former Vice President Al Gore will be in the final phase of his reinvention and an all-but-announced candidate for the 2008 Democratic presidential nomination. If Clinton defeats Giuliani, she reasserts her claim as the front-runner. If she loses, Gore becomes the front-runner and the dream of a Clinton restoration dies.

It’s been a long while since politics has been a big New York story. No one cared if George Pataki beat Carl McCall or if Chuck Schumer beat Al D’Amato. And on a national level, it couldn’t have mattered less. Who wins the Giuliani-Clinton race matters a lot, and on a lot of levels.

Think of this as a movie trailer. The movie should open on schedule just after election day, 2004.

John Ellis, a partner in a venture capital firm in New York City, is a contributing columnist for