It was not clear what prompted Mr. Flood to sign on. The president’s legal team for the special counsel investigation has been marked by turnover and uncertain strategy, complicated by a client liable to dismiss his lawyers’ advice. That factor prompted Mr. Trump’s lead lawyer on the case, John Dowd, to quit this year. Rudolph W. Giuliani, the former mayor of New York who is a longtime confidant of the president, has come on board pledging to negotiate an interview for the president with the special counsel.
Emerging as part of those negotiations, a set of questions from the special counsel, Robert S. Mueller III, shows that he wanted to quiz Mr. Trump on an exhaustive array of subjects, including his contacts with Russia as well as his mind-set leading up to and during a number of acts that could construe an attempt to obstruct the inquiry itself.
Mr. Flood was part of a team of lawyers who represented Mr. Clinton during his impeachment proceedings. Though he did not have a high-profile role, Mr. Flood did attend the Senate’s deposition of Mr. Clinton’s lawyer and confidant, Vernon E. Jordan Jr.
Mr. Flood was also the lead lawyer in the White House Counsel’s Office during George W. Bush’s second term in dealing with congressional investigations, including the examination of the Bush administration’s decision to dismiss seven United States attorneys. In private practice, Mr. Flood represented former Vice President Dick Cheney.
Mr. Flood is well regarded in the conservative legal world and has connections with key players that could make him more effective than his predecessors on the legal team, including a good relationship with Donald F. McGahn II, the White House counsel.
Mr. Flood is himself seen as a prospective replacement for that job, potentially providing a smooth exit ramp for Mr. McGahn, who has clashed privately with Mr. Trump and whose departure has long been rumored.
Mr. McGahn spearheaded the effort to bring in Mr. Flood. Mr. McGahn and his personal lawyer, Bill Burck, who is close with Mr. Flood, convinced him over the past several weeks to join the administration.
Mr. Cobb arrived at the White House last summer as some of Mr. Trump’s friends and advisers encouraged the president to fire Mr. Mueller. Mr. Cobb feared that the special counsel was on the verge of issuing subpoenas demanding documents and testimony from White House aides, a move that could have locked the administration in a contentious court fight it was certain to lose. Instead, he repeatedly declared the White House to be in “full cooperation mode.”
He said publicly that the White House had no interest in firing Mr. Mueller, and told friends privately that he would not remain in the administration if Mr. Trump moved to fire the special counsel.
“There is not and will not be any consideration of terminating the special counsel, Bob Mueller,” Mr. Cobb said in an interview in October. “I think the path that he chose of trying to minimize conflict and maximize cooperation is one that benefits the country.”
Mr. Cobb’s hiring appeared to have a soothing effect on the president last year. He repeatedly assured Mr. Trump and the public that the Mueller investigation would end quickly — first by Thanksgiving, then by the start of the new year. Whether that was wishful thinking or an effort to calm an irascible president, Mr. Cobb’s prediction proved incorrect.
Behind the scenes, as Mr. Cobb rushed to turn over records to Mr. Mueller, his relationship soured with the White House counsel, Donald F. McGahn II, who thought Mr. Cobb should have more thoroughly reviewed documents and been willing to assert executive privilege. Mr. Cobb in turn thought that Mr. McGahn’s early response to the investigation had been too slow, bringing the White House to the verge of a subpoena.
Mr. Cobb, a longtime white-collar defense lawyer, was not a supporter of the Trump campaign and never viewed himself as part of that team. He has donated money to both Republicans and Democrats and supported Jeb Bush for president in the 2016 election.
He joked that he had “rocks in his head” as he took the job, and told friends that he expected to stay at the White House only as long as it took to turn over all the information to Mr. Mueller and arrange staff interviews with prosecutors. That job is nearly complete, with only Mr. Trump’s interview with prosecutors still being negotiated.
As for Mr. Flood, he has already had a whiff of the drama that follows Mr. Trump. Following a New York Times report in March that Mr. Trump was in discussions to hire Mr. Flood, the president attacked the article and one of the reporters who wrote it.