Glenn Thrush is senior staff writer at Politico Magazine.

It’s oddly fitting that Attorney General Eric Holder – a stubbornly independent career prosecutor ridiculed by Barack Obama’s advisers for having lousy political instincts— would nail his dismount.

But Holder, who began his stormy five-plus-year tenure at the Justice Department with his controversial “Nation of Cowards” speech, has chosen what seems to be the ideal (and maybe the only) moment to call it quits after more than 18 months of musing privately about leaving with the president and senior White House adviser Valerie Jarrett, a trio bound by friendship, progressive ideology and shared African-American ancestry.


It was now or never, several current and former administration officials say, and Holder – under pressure to retire from a physician wife worried about a recent health scare, checked the "now" box. “It was a quit-now or never-quit moment,” one former administration official said. “You didn’t want confirmation hearings in 2015 if the Republicans control the Senate. So if he didn’t do it now, there was no way he could ever do it.”

Holder—described by associates as President Obama’s “heat shield” on race and civil rights—sprung it on the president over the Labor Day holidays. Obama didn’t bother to push back as he has in the past, even though staffers say he winces at the prospect of a long confirmation battle, whomever he chooses for the nation’s top law enforcement job.

Holder’s announcement gives Obama several weeks to pick and vet a successor who would face confirmation hearings in the lame-duck session after the midterms. Holder has “agreed to remain in his post until the confirmation of his successor,” a top Justice Department aide said, as an insurance policy against GOP foot-dragging.

His timing also has a personal dimension. The keenly legacy-conscious Holder has never been in better standing, leaving on arguably the highest personal note of his tenure, after a year of progress on his plan to reform sentencing laws and just after his well-received, calming-the-waters trip to Ferguson, Missouri, during the riots in August. In a background email to reporters, a senior Justice Department official struck a victory-lap tone, writing, “The Attorney General’s tenure has been marked by historic gains in the areas of criminal justice reform and civil rights enforcement. The last week alone has seen several announcements related to these signature issues.”

That’s a striking contrast to the defensive posture of the last few years, when Holder became the first sitting Cabinet official to be found in contempt of Congress. Hill Republicans, who have warred with Holder for years, greeted his departure with don’t-let-the-door-hit-you-on-the-way-out glee. “I welcome the news that Eric Holder will step down as Attorney General,” said House Judiciary Committee Chairman Bob Goodlatte, in an email. “From Operation Fast and Furious to his misleading testimony before the House Judiciary Committee regarding the Department’s dealings with members of the media and his refusal to appoint a special counsel to investigate the IRS’ targeting of conservative groups, Mr. Holder has consistently played partisan politics with many of the important issues facing the Justice Department.”

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At the moment, there’s no obvious replacement, several officials close to the situation told me. W. Neil Eggleston, the new White House counsel, will lead the search with an assist from Jarrett, Holder’s longtime ally and defender. Obama and his team would probably prefer a known and trusted quantity—like Massachusetts Gov. Deval Patrick, a potential future Democratic presidential candidate who served as the head of the department’s civil rights division under Bill Clinton. But Patrick, who is friends with Obama insiders like David Axelrod, who still advises his old boss informally, has repeatedly told them he’s not interested, and – for now—he seems to mean it. When asked by reporters today, Patrick snapped, “I am going to finish my term and then head into the private sector.”

Paul J. Richards/ AFP/Getty Images

Solicitor General Donald Verrilli, Jr. is a favorite of Obama’s, and a person valued as a team player inside the West Wing—not as widely known but someone who might have an inside track, thanks to Obama’s penchant for picking trusted insiders over high-profile outsiders. But liberal critics have faulted Verilli for his halting performance defending the Affordable Care Act before the Supreme Court, as well as his mixed scorecard overall.

In recent days the president’s team has also taken a close look at California Attorney General Kamala Harris, an African-American woman who would likely pursue the same civil rights agenda championed by Holder—but may opt to stay in her state to pursue gubernatorial ambitions.

Other names under consideration, but considered less likely, according to check-ins with half a dozen current and former West Wingers: Preet Bharara, U.S. Attorney in Manhattan known for his aggressive Wall Street prosecutions; Ron Machen, the young U.S. attorney for Washington, D.C.—a job once held by Holder; Connecticut Sen. Richard Blumenthal, a former state attorney general; former Joe Biden aide Neil MacBride, an ex-federal prosecutor in Virginia who is now a partner at the law firm Davis Polk; ex-White House Counsel Kathryn Ruemmler, another Obama favorite; and Labor Secretary Tom Perez, another former head of the civil rights division—and currently the only Latino candidate mentioned by insiders.

There’s also at least one high-profile long-shot on the informal list being circulated inside Obama’s camp: former Department of Homeland Security Secretary Janet Napolitano, who left Washington in 2013 to take over the massive University of California system, according to one Democrat with close ties to the White House. Napolitano was the original choice for the job at the start of Obama’s first term – a favorite of then-Chief of Staff Rahm Emanuel. Holder, who had considered himself the sole front-runner for the job, was startled during the 2008-09 transition period when he was handed a Department of Justice binder that included headshots of himself and Napolitano as potential AGs.

The Holder-Napolitano rivalry was legendary: Once, after the former Arizona governor asked Holder about his future plans, the AG joked to a friend, “Sometimes I feel like Janet is touching me just to see if I’m still warm.”

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What’s clear is that Holder, for all the headaches he gave Obama’s team, filled a one-of-a-kind role in Obama’s administration and the president’s personal life that will likely never be filled again.

On no issue is that more true than race—a subject on which current and former Obama administration officials and confidants of both men say that Holder has been willing to say the things Obama couldn’t or wouldn’t say.

“He’s a race man,” Charles Ogletree, a longtime friend of Holder’s who taught and mentored Obama and his wife, Michelle, as Harvard Law School students in the 1980s, told me earlier this year for a profile of the attorney general in POLITICO Magazine. “He’s gone farther and deeper into some issues of race than the White House would like, but I know he has the president’s well-wishes. It’s clear [Obama and Holder] believe in the same things.”

And Holder himself recently told another African-American friend that he feels part of his job is “to talk about things the president can’t talk about as easily.”

In part, that’s why Obama long resisted calls, from inside and outside the administration during the first term, to dump Holder, including quiet rumblings by some aides who wanted Obama to ease him out after the 2012 reelection.

He is one of the few administration figures to cross the threshold from employee to friend of the famously reserved president. Holder, in fact, is one of the only Cabinet members Obama routinely invites over for dinner and drinks (Education Secretary Arne Duncan, a hoops buddy from Chicago, is another) and the only one who times his summer vacation to hang out with the president on Martha’s Vineyard.

Their wives are even closer, and Michelle Obama is a not infrequent drop-in guest for Friday pizza night at Holder’s house. Besides, the attorney general is nothing if not a loyalist, an increasingly valuable commodity to a second-term president rattled by accelerating congressional investigations. Obama clearly respects Holder’s four decades of experience as an attorney and judge and supports Holder’s positions on LGBT rights and racial profiling, often telling his staff he recognizes it’s not all Holder’s fault: The job of attorney general is a “shit magnet” for the most intractable controversies.

That was never truer than during the aftermath of the Trayvon Martin verdict in 2013, when Holder criticized Florida’s “stand your ground” laws and expressed sympathy for the slain teen’s family. A few days later, Obama appeared in the White House briefing room to echo those comments, memorably proclaiming “Trayvon Martin could have been me.”

Holder’s departure has long been speculated, and he has discussed his plans with the president “on multiple occasions in recent months,” a Justice Department official said. One sign he was on the way out, noticed recently by the Al Kamen of the Washington Post: Holder was scheduled to travel to the U.S. Attorney’s office in Scranton, Pennsylvania, the last of 93 federal prosecutors’ offices he had vowed to visit as attorney general. Holder saved the Middle District of Pennsylvania for last because he won his first case as a Justice Department trial attorney there in the late 1970s, his staffers said.

Valerie Jarrett, center, helped make sure Holder got the AG job over Janet Napolitano, left. | Larry Downing/Reuters/CORBIS

Holder, for his part, seems to be looking to keep building a racial legacy outside of government. “The attorney general has no immediate plans once he steps down,” said a top Justice Department official. “He does, however, wish to stay actively involved in some of the causes to which he has devoted his time in office. In particular, following his recent visit to Ferguson, Missouri, he has spoken with friends and associates about his wish to find a way, even after rejoining private life, to continue helping to restore trust between law enforcement and minority communities… Holder is uniquely positioned to help lead such a project.”

For Barack Obama, life without Holder means the departure of yet another close friend and trusted veteran who was present at the creation of the Obama phenomenon in 2008 and gutted it out through the administration’s toughest battles.

Obama didn’t draft a formal plan for his second term, but he did make a point of inviting most of his Cabinet members to the Oval Office for check-in sessions after the 2012 campaign, including interviews with a few he wanted out. The exception was the attorney general—and Obama didn’t give him much of a chance to say no.

After one Holder-Obama dinner in late 2012, the president offhandedly asked Holder, “So, Eric, are we good?”

Holder, who had been mulling his departure at the time, said, “Yeah,” and left it at that.