Among the myriad sensitive matters requiring Eggleston's expertise, Boehner's suit is an unexpected challenge he must prepare for without knowing exactly the legal arguments it will make. In his first interview since coming to the White House this spring, Eggleston predicted the matter will be quickly dismissed by a judge for a lack of legal standing.
"As I used to tell clients in private practice, anybody can sue anybody over anything," Eggleston told The Associated Press from his West Wing corner office. "The fact that he's going to say that he's going to bring some lawsuit is not going to affect what the president is going to do."
Eggleston's guidance of the legal limits of Obama's executive actions draws from experience working across all three branches of government early in his career. He clerked for Chief Justice Warren Burger, a conservative chosen by President Richard Nixon, and later worked for the House Select Committee investigating the Iran-Contra affair. He was in President Bill Clinton's counsel's office during oversight hearings into the Whitewater real estate transactions and later helped fight subpoenas of presidential aides in the Monica Lewinsky investigation.
In private practice, he represented white-collar clients, including the outside directors at Enron after the company's financial collapse. His political clients included Chicago Mayor Rahm Emanuel as a witness in the corruption trial of former Illinois Gov. Rod Blagojevich. He also represented former Cabinet secretaries Federico Pena and Alexis Herman when they were facing investigations that did not result in charges.
Sara Taylor Fagen, President George W. Bush's former political director, hired Eggleston when she was subpoenaed in a congressional investigation into White House involvement in the firings of U.S. attorneys. The White House advised her not to testify, but Eggleston escorted her to Capitol Hill and sat by, telling her which questions she could answer without violating Bush's claims of executive privilege.
"He completely led the White House counsel out of a tricky situation when it should have been the other way around," Fagen said.
Obama didn't know Eggleston until outgoing counsel Kathy Ruemmler recommended him as her replacement. After he was chosen, she arranged a Camp David retreat for administration lawyers to get to know Eggleston. She "played Charlie Rose," interviewing him before the group about growing up the son of a lawyer in Indiana, his experiences with Clinton and his management style.
Eggleston advises Obama on diplomatic policy, congressional investigations and judicial nominations, including preparation for a possible Supreme Court vacancy. He's also a national security adviser on issues such as counterterrorism operations, like the capture of terrorism suspect Ahmed Abu Khattala, and the fallout of government surveillance disclosures by whistleblower Edward Snowden.
Eggleston's financial disclosure report shows he has assets worth between $15 million and $43 million. He says part of how he's built that wealth is that he is not much of a spender — he has one home in Chevy Chase, Maryland, and drives an 8-year-old car. He paid college tuition only for his daughter, a member of the Teach For America corps in Rhode Island, while his son is attending Eggleston's alma mater, Duke University, on a soccer scholarship. He traveled to Tuscany last year as part of a cycling group he helps organize, but his other summer trips have been to the more modest destinations of Vermont and Iowa.
Eggleston said he has no qualms about coming back into government service amid so many challenges.
"To me, that's even better," he said with a smile.
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