Along with many other observers, I assumed that whatever problems a Giuliani presidential campaign might face, fundraising wouldn't be one of them. New York City is home to many of the nation's leading political donors (of both parties), large Republican givers are often moderate-to-liberal on cultural issues, Giuliani's speaking gigs have put him in touch with many corporate leaders, and he is just the kind of guy CEOs like. On the other hand, I wondered about Giuliani's ability to put together a first-rate campaign staff. He has always relied heavily on a tight-knit (some might say sycophantic) inner circle, often noted more for personal loyalty than for knowledge of national politics or even intelligence or integrity. He's not the easiest man to work for, and hates to share the limelight (as Bill Bratton, perhaps the most successful policymaker in recent history, discovered).
Recent weeks have turned these judgements on their heads. Rudy has hired some prominent staffers, many of them veterans of the RNC or national campaigns. He's still not on the same level as McCain or Romney, but it's a start. Meanwhile, a December fundraiser at a Times Square hotel seems to have underperformed, with mostly "Rudy people" in attendance. At the same time, McCain's campaign announced the support of several leading NYC-area Republican fundraisers / socialites: Henry Kissinger, Henry Kravis, Georgette Mosbacher and Lewis Eisenberg (the last two loom especially large in moderate GOP circles). If Rudy can't raise money from rich, socially liberal Republicans on the Upper East Side, who can he get it from?
To me, the most interesting aspect of the leaked memo was the number of top fundraisers Giuliani was targeting last fall who have instead signed up with other candidates. The document was absolutely correct in arguing that Giuliani needs to raise $100 million or more this year. Should he run, he will face a barrage of negative attacks, both from social conservatives and from the NYC tabloids. (And don't forget Donna Hanover!) He'll need to respond. To raise that kind of dough, that will require both a strong network of fundraisers and months of commitment from the candidate himself -- both of these seem questionable now. Expectations will be high for the rollout of his campaign; Rudy has to go big or not at all. A Sam Brownback or Frank Keating can start small and nurture the grassroots for weeks on end; Giuliani doesn't have that option.
And if McCain's crew is starting to pressure donors to "get on the bus" before it's too late, it won't be the first time. In 1999, an old friend who was working for another Republican candidate, who had to withdraw due to lack of funds, told me that the George W. Bush campaign was leaning hard on top Republican moneymen not to give to any other candidates.