Orin Kramer, King of the New York Obamasaurs

For all his quirks, though, Mr. Kramer is widely recognized as a serious financial and political thinker. A graduate of Yale University, where he roomed with former New York Governor George Pataki, and then Columbia Law, he is an accomplished investor and policy wonk. He entered President Jimmy Carter’s administration at the age of 31 as an associate director on the domestic policy staff, and became the White House’s point man for dealing with New York’s fiscal crisis.

Mr. Kramer is still active in public policy. He monitors New Jersey’s $82 billion public pension fund, wrote the strict 2004 regulations preventing outside managers of New Jersey money from making campaign contributions and is the subject of articles in Pensions and Investments. (“Kramer Eerily Clairvoyant,” read one headline.) He’s close to Governor Jon Corzine, and remains a player in New Jersey power politics.

But it is Mr. Kramer’s reputation as a prodigious fund-raiser that matters most to the Obama campaign.

Once a major donor to the presidential campaign of Al Gore, and then a national finance chairman for John Kerry’s presidential campaign, Mr. Kramer was a natural fit for Hillary Clinton’s camp. But he had something of a relationship with Mr. Obama. They were first introduced in 2003 by Mr. Corzine, then the head of the Democratic Senatorial Campaign Committee, during Mr. Obama’s Senate campaign. Mr. Kramer and his wife, Columbia art history professor Hilary Ballon, met Mr. Obama for lunch at the Four Seasons in New York, and Mr. Obama stayed in touch, even calling to comment positively about an article Mr. Kramer wrote about tax policy in The American Prospect.

(Mr. Kramer said the calls spoke more to Mr. Obama’s political instincts than the originality of his own thinking on taxes.)

In the weeks before the presidential campaign got underway, Mr. Kramer, like other highly sought-after Democratic bundlers, received briefings from Mark Penn, Mrs. Clinton’s senior strategist, and David Plouffe, Mr. Obama’s campaign manager. Mr. Kramer told both men, and others, that he was convinced the country was hungry for change and that Mr. Obama amounted to an extraordinary political talent. He received daily calls from the Clinton campaign and his friends supporting her, but in January 2007, when he was already leaning for Mr. Obama, he ate a steak dinner with the candidate at a Ruth’s Chris Steakhouse near Dupont Circle with the core of Mr. Obama’s New York support, including fund manager Jim Torrey, Mr. Mathis, Citibank executive Michael Froman and private-equity manager Jamie Rubin. In the airport on the way back to New York, he called Jonathan Mantz, Mrs. Clinton’s finance director, to break the bad news.

“When he called me to tell me he was going to do this, he said, ‘Does the word suicidal come into mind?’” said Hassan Nemazee, a friend of Mr. Kramer who was one of Mrs. Clinton’s national finance chairs. “It showed tremendous political acumen.”

Mr. Kramer’s decision shocked the donor establishment in New York.

“Jonathan [Mantz] was really upset. I was really upset,” said Maureen White, one of Mrs. Clinton’s major donors, who is now actively raising money for Mr. Obama. “I don’t think I had gone through a presidential campaign in recent memory that I hadn’t talked to Orin every day. I jokingly said that the only thing I held against Obama was that he took Orin away.”

Ms. White said Mr. Obama greatly benefited from Mr. Kramer’s decision because “even if you look at their national finance committee, very few of them have been involved in a major way in a presidential campaign before this one.”

“The Clinton people worked very hard to make sure there was no leakage in their own base,” said Mr. Schlosstein. “If you put together a list of the top five fund-raisers, Orin would be on it. It was a high-risk decision. As a consequence relatively few people did that.”

Mr. Kramer maintained friendly relations with his friends in Hillaryland, even placing friendly wagers on the Pennsylvania primary.

“It was a $100 bet that we would win by ten points,” said Mr. Nemazee. “I called him up that night and said, ‘We’ve won by 10 points.’ It was announced on CNN and Fox and everybody that we won by ten. The next day there was an envelope with 100 dollars cash in my office. And a day later I get a call from Orin: ‘I can’t believe you Clinton people. This is why we hate you so much. You win by 9.4 percent and instead of rounding it down to nine percent, you round it up to ten and take our hard-earned money.’”

Mr. Nemazee returned the hundred dollars.