Picture a November contest between Sen. Barack Obama and Rudy Giuliani. Not only would it feature the first African-American major-party presidential nominee against the first Italian-American, it would resonate with regional history in a unique way.
Giuliani's single loss at the polls, in 1989, made David Dinkins New York City's first black mayor - until Dinkins, staggered by the Crown Heights riots, lost the rematch to Giuliani in 1993. For the next eight years, political relations between City Hall and black communities ranged between cold and contentious.
In his push for the White House, Giuliani clearly has been bent on facing Sen. Hillary Rodham Clinton, who'd be the first female major-party presidential nominee. His fundraising letters specifically tout him as the Republican best suited to stop her. His campaign appears....
Dan Janison
.... to calculate that the heavy Clinton family baggage would offset his own. Obama, however, may offer a different story for the ex-mayor, or any Republican.
In 1989, Giuliani seemed psyched and ready to unseat Mayor Ed Koch, but Koch foiled those plans by losing the Democratic primary to Dinkins, who then won in November. In 1997, on the other hand, Giuliani secured support from many white Democrats and cruised to a second term by defeating Ruth Messinger - the city's first female Democratic mayoral nominee.
In Saturday's televised Republican debate, you could see the ex-mayor jury-rig his message as GOP contenders were asked about Obama. Giuliani gave the general knock: "He's never run a city, never run a state, never run a business." He put down Obama's need for "on-the-job experience" and warned he could bring "bad change" on taxes and in foreign policy.
We got an early taste seven months ago when Giuliani described the Democrats as "waving the white flag" in Iraq. Obama shot back: "Rudy Giuliani today has taken the politics of fear to a new low and I believe Americans are ready to reject those kind of politics." Polls show Obama at the moment leading Giuliani by 10 points.