The debate, to be moderated by MSNBC's Chris Matthews, appears to be unprecedented in the annals of presidential politics in that no other candidate has ever before challenged himself to a one-on-one face-off.
But speaking from his campaign headquarters in New York today, Mr. Giuliani appeared upbeat about his prospects of beating himself.
"I know exactly what to expect from me, and I will be prepared," he said. "May the best Giuliani win."
Plans for the debate are already well under way, including a stage set with two podiums, which Mr. Giuliani will shuttle back and forth between when switching from his pro-abortion stance to his anti-abortion one.
Campaign insiders say that the Giuliani-Giuliani debate is a "win-win" for the campaign, since it will show that the former New York mayor can appeal to voters on both sides of the abortion issue simultaneously.
But some observers raise a red flag of caution, remembering a similar plan from the 2004 presidential race in which Sen. John Kerry (D-Mass.) was to have debated himself on the war in Iraq.
The plan for the Massachusetts senator to debate himself on Iraq was ultimately scuttled by Mr. Kerry himself, who memorably told reporters, "I was for the idea of debating myself before I was against it."
Elsewhere, JetBlue founder David Neeleman said that he does not know exactly when he is departing the company because he is departing on JetBlue.
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