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Obama’s charm offensive in his early days in D.C. has helped him crack a demographic that at one time seemed destined for total domination by Hillary Clinton: elite Washington lawyers — including many who served in Bill Clinton’s administration.

On a warm fall evening in 2004, not long after he was elected to the U.S. Senate from Illinois, Barack Obama attended an intimate Washington dinner party. Seated next to him was Covington & Burling’s Eric Holder Jr. — a high-profile litigation partner and former deputy attorney general in the Clinton administration.

The two men chatted about politics, the Justice Department and the law, and “just kind of hit it off,” Holder says.

Obama had been doing the D.C. dinner party and fundraising circuit for some time during his Senate run. Months earlier, he was at Vernon Jordan Jr.’s home, and there he met and wowed Gregory Craig, a star at Williams & Connolly and a former Clinton appointee. As Jordan puts it, Craig has “been in love with [Obama] ever since.”

Even Jordan, who remains an enthusiastic backer of Sen. Hillary Clinton and is still one of the most famous friends of former President Bill Clinton, has helped out Obama — contributing $2,300, or half what he’s given Hillary Clinton in her bid for the Democratic presidential nomination.

Obama’s charm offensive in his early days in D.C. has helped him crack a demographic that at one time seemed destined for total domination by Hillary Clinton: elite Washington lawyers — including many who served in Bill Clinton’s administration.

Holder is Obama’s national campaign co-chairman. Craig, who was an assistant to the president and special counsel in the Clinton White House, is a foreign policy adviser. Bryan Cave’s Broderick Johnson, Clinton’s liaison to the House of Representatives, is an informal political adviser.

“The reality is that I served in that first Clinton administration, and I owe them a great deal,” Holder says. “But at the end of the day, what was critical for me was what’s most important for my country and my party. And I really thought that Barack would be a superior president.”

For Holder, that 2004 dinner party got him started on the realization that old loyalties would have to take a back seat during the 2008 presidential race.

Bill Clinton nominated Holder, then in his early 40s, to become the first African-American U.S. Attorney for the District of Columbia in 1993 — a position he held for nearly four years. In 1997, Holder became the No. 2 at Justice, when Clinton appointed him deputy attorney general. He was also the first African-American to hold that position.

For Obama, Holder has worked on wooing superdelegates, as well as advising the senator on policy issues and speeches, including the one he gave at Howard University in September. Even at work in Covington’s Pennsylvania Avenue Northwest office, Holder has Obama on the brain. He says about 20 lawyers in the office keep up-to-date with campaign events on an e-mail chain.

Williams & Connolly’s Craig has an even longer history with the Clintons, whom he first met in 1971 when all three attended Yale Law School together. In 1998, President Clinton turned to him to lead the defense team fighting his impeachment.

It’s only fitting, then, that Craig met Obama through Clinton’s friend and former adviser Jordan, now senior counsel at Akin Gump Strauss Hauer & Feld. Craig was invited to a fundraiser that Jordan hosted at his home in 2003 during Obama’s run for the Senate. From there, Craig says of Obama, “I became convinced that he had the ability to bring people together, and to end the partisan bickering in a way that no one else did.”

Craig, who says he hasn’t seen or talked to the Clintons since the presidential campaign began, has helped Obama prepare for debates by offering foreign policy advice and has helped negotiate terms and format issues with debate sponsors. He’s a member of Obama’s national finance committee and has acted as a surrogate addressing foreign policy questions from the media and the public during the primaries in New Hampshire, Texas, and Ohio.

The Obama camp’s No. 1 lawyer is its lead outside counsel, Robert Bauer, of Perkins Coie’s D.C. office. He served as counsel to Democrats in the House during the 1999 impeachment trial and is also counsel to the Democratic Senatorial and Congressional Campaign committees. Bauer didn’t respond to requests for comment.

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