What Happened to Eric Holder?

He was a Reagan-appointed judge and a Clinton-appointed prosecutor respected by both sides. Then it all fell apart.

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Nineteen years ago this month, Eric Holder was having a very different spring in Washington. It wasn't cruel or grueling. Conservatives didn't want his scalp and liberals didn't think he was trampling on civil liberties. In 1994, Holder was just into his tenure as the federal prosecutor for Washington, D.C. The 43-year-old had come to the U.S. Attorney's job with the credentials of a quiet careerist, joining the Department of Justice in 1976 and serving 12 years as a prosecutor before Ronald Reagan appointed Holder to be an associate judge in D.C. Superior Court in 1988.

As U.S. Attorney, Holder took over the prosecution of Dan Rostenkowski--"Rosty," the Boss, the chairman of the House Ways and Means Committee. And Washington asked: Would this tall, thin, mild-mannered guy who everyone knew at the courthouse be able to put Rosty away--especially now that Holder had been appointed by a Democratic president who needed the lawmaker behind the passage of so many bills? Rosty's lawyer, the famed Bob Bennett, knew Holder, understood how tough he was and begged his client, the Chicago pol, to take a deal. Rosty refused and fired Bennett. That was a bad idea. Holder issued a searing 17-count indictment for everything from putting ghost jobs on his payroll to embezzling from the House Post Office. "Today's indictment of Congressman Rostenkowski should stand as a firm and solemn reminder that the Department of Justice has an unwavering commitment to hold accountable all those who engage in corruption," a much less gray Holder said in front of the microphones. Rosty eventually pled out and went to jail. Holder had distinguished himself that day as the Democratic prosecutor who took out a leading Democrat.

Of course, Holder now seems distinguished primarily by the mob out to get him. Arianna Huffington wants his head. So does Rep. Pete King, the New York Republican. And plenty of Democrats wouldn't mind seeing him go. He's been slammed for everything from the botched "Fast & Furious" case that left a Border Patrol agent dead to a warrant that named a Fox News reporter as a potential co-conspirator in a leak case. Thursday was a typical day for Holder. Holder's testimony before a routine Senate Appropriations Committee hearing for the Justice Department's budget was overshadowed by his announcement he would not seek Rosen's prosecution and defending but not explaining the revelation of a massive subpoena of phone records from Verizon.

The celebrated young man has become a bruised 62-year-old. Yes, his stewardship of the department includes many accomplishments from defending the health care law to putting terrorists behind bars. Yes, he still has the lean looks of the Columbia University basketball player he was. But now Holder's got that Washington-is-slowly-killing-me look, too. Still, the president still stands behind his close friend so no one close to Holder expects him to leave anytime soon--maybe the end of this year or the beginning of 2014 and only after the national security team is settled in and there's a new FBI director. But whenever he goes, Holder will leave with many friends scratching their heads over how a talent who came of age at the Justice Department and spent more time working in its halls than any attorney general in modern memory could have had such a rocky tenure.

The answer is that no one thing led to this moment. It's a combination of many factors including the impossible life of an Attorney General. Janet Reno, John Ashcroft, Alberto Gonzales--all had targets on their back and only Michael Mukasey, who came in at the end of the Bush years to clean up, was exempt and that's because he was there so briefly. The bigger problem, though, may not be the job but Holder's own inability to navigate the political shoals within his building as well as the world outside--Congress, the media and, ironically with a White House where he enjoys the closest personal relationship with the president of any Cabinet member.

"He's not very political, contrary to popular belief," observes Joseph DiGenova who was also the U.S. Attorney for Washington, D.C. A prominent Republican, a Washington fixture, and a fellow Reagan appointee, DiGenova has known and liked Holder for decades. He endorsed Holder for A.G. and said he'd do it again. But DiGenova also sees a number of missteps -- most notably Holder's failure to navigate the politics within "Main Justice," the term of art for the department's headquarters on Pennsylvania Avenue where zealous careerists can put an attorney general in jeopardy. DiGenova believes Holder should have stood up to the department's Criminal Division's unprecedented naming of Fox News's James Rosen as a co-conspirator instead of signing off on it. DiGenova chides Holder for refusing to turn over more documents to House investigators in the Fast & Furious case, which led to a contempt citation against Holder. He notes that department lawyers always advocate turning over as little as possible but an attorney general needs to know better. By contrast, DiGenova hails Holder's dropping the federal corruption case against the late Sen. Ted Stevens of Alaska as the attorney general's "finest hour"--a time when the AG knew how to rebuff the overzealous careerists in the Public Integrity Section where Holder had begun his career.

Other friends and colleagues of Holder, most of whom declined to speak on the record for fear of angering Holder or hurting him, echo the notion of Holder as politically tone deaf and not having the right kinds of people around him to help deal with explosions that are inevitable. After all, the attorney general stands at the crossroads of terrorism, war, race, civil rights, banking, and any number of messes.

"There are two things that have undermined him: He doesn't have great political judgment and he manages those issues himself. He doesn't compliment his own skills with people who do [have them]," says one longtime Washington attorney who has worked with Holder.

Filling out an Attorney General's staff with political players is tricky since the Justice Department is supposed to be apolitical. Surrounding the Labor Secretary with political operatives wouldn't raise complaints. That's not true at DOJ. When the Attorney General is a political player (Bobby Kennedy, John Ashcroft), it's less necessary. Where they're not--as with Janet Reno--it helps to have senior staff who have the legal chops to reassure DOJ staff and the political sensibilities to deal with the outside world. (Ron Klain worked for Reno and went on to be chief of staff for both Al Gore and Joe Biden played this role.) Holder had few people like that around him in the first term although he's about to get an infusion when Brian Fallon, a veteran of Sen. Chuck Schumer's office, comes aboard in the next few weeks. But some friends worry that Holder's problem won't be alleviated by picking up staff from the New York Democrat. He isn't in need of a verbal martial arts master, they argue, but a more acute radar for sensing incoming crises and managing them the DOJ way. They note that Holder was caught off guard by the blow up over the Rosen subpoena and they think his handling of it since--defending it, saying he had regrets about it, and then saying today Rosen wouldn't be prosecuted although Rosen's not been given any official all-clear notice has made a bad decision worse. "Say it is wrong or own it," says the Washington attorney.

What's most alarming among those who know Holder and like him is their despair over how the straight arrow they adore is now seen as hyperpartisan, dissembling, even perjuring. Holder, they note, was the studious son a father who immigrated from Barbados and whose mother was a church secretary and whose brother is a cop. The wiry athlete leapt from his middle-class home in Elmhurst, Queens to the city's elite Stuyvesant High and then Columbia College and Columbia Law School and eschewed big bucks on Wall Street to go straight to the Justice Department. (He once had to listen to a wiretap of a mobster referring to him by a racial epithet.) He only started to make money in 2001 when he joined the ranks of government lawyers at Covington & Burling, where he represented the odd assemblage of clients that goes with being a big-name, white-shoe attorney--the NFL in the Michael Vick case and a group of irate trustees at American University fighting over Ben Ladner, who left the school's presidency after details of his lavish lifestyle emerged. They note that he'd been confirmed overwhelmingly by the Senate before his nomination to become attorney general and even then he received the support from the likes of Republican Sens. Jon Kyl, Orrin Hatch and John McCain and endorsements from Republicans like Fran Townsend, George W. Bush's Homeland Security Advisor and Louis Freeh, the Clinton nemesis and former FBI Director.

But they also note that since he became the Deputy Attorney General in the second Clinton administration in 1997 Holder became more controversial. As with many mountains, the closer you get to the summit, the more treacherous it becomes. Some things Holder handled adroitly. He won plaudits from Republicans, and eyerolls from Democrats, for giving Clinton Prosecutor Kenneth Starr permission to expand his investigation. But he also made critics out of supporters for his role in the pardon of fugitive financier Marc Rich in the last days of the Clinton administration. At the request of Israel's prime minister and others, Clinton granted Rich a pardon and the case was not given the thorough vetting that most pardons get at the Justice Department. Holder later said that he regretted not having done more to speak out about the Rich pardon although the president had complete discretion to dole out clemency as he sees fit. Still, it became an issue at Holder's confirmation hearings and it was, perhaps, a sign of things to come. He had been confirmed 100-0 for the Clinton Deputy AG job in 1997. But in 2009, he lost 21 votes when he was up for AG. Going from the work of being a prosecutor--taking a case and managing it--to managing staffs, bureaucracies, the press, a meddlesome White House and an irritable Congress didn't seem to be what Holder liked or where he was at his best. And he faced a Republican Congress willing to pounce.

Still there were plenty of unforced errors. Remarkably, Holder began his tenure with two gaffes in a week. First, he inserted the phrase "nation of cowards" in a Martin Luther King Day address. While Holder's point about America not wanting to discuss its racial history was familiar, if not anodyne, even the president distanced himself from the clumsy comment. Later in the week Holder said that he'd push ahead with the ban on assault weapons earning the wrath of red state Democrats on the Hill and Rahm Emanuel, then-White House Chief of Staff.

Holder often found himself on Emanuel's bad side, which hardly made him unique. But he seemed to have a poor sense of when to push and when not to. After the decision to try terrorist Khalid Sheikh Mohammed in civilian court was made, the White House wouldn't let Holder sell the idea and had him keep mum, a point noted by Dan Klaidman in his book Kill or Capture: The War on Terror and the Soul of the Obama Presidency. New York politicians, mostly Democrats but including Mayor Michael Bloomberg, denounced hosting the trial. The administration backed down and Holder took much of the blame. "They wanted him to run the Gitmo group and quietly get rid of Gitmo," recalls one Holder colleague. "They completely underestimated what it would take."

In the "Fast & Furious" case, a botched gun-and-drugs operation that left a Border Patrol agent dead, Holder received a contempt of Congress citation, the first for a Cabinet member, for not turning over more documents related to the case--documents which Republicans suggested could show Holder misstated when he knew about the case. DOJ colleagues of Holder insist that they had complied with the requests from House Oversight Committee Chairman Rep. Darrell Issa and they defend the decision to withhold documents. An Inspectors General report concluded that there was no evidence that he knew about it early. Still before it was over 17 House Democrats had voted with Republicans for the contempt citation. Some friends say it was a case where Holder should have just given over more documents. "I don't understand the stonewalling," says DiGenova.

Holder is surely a victim of the times. The great work of the Justice Department from the Bureau of Prisons to the Civil Rights Division to the FBI gets little day-to-day attention, especially as the media cuts its coverage, and each dust up is magnified a hundred fold. "I've come to the conclusion that unfair attacks are inevitable," says David Schertler, who served with Holder as a prosecutor and is a prominent criminal defense lawyer in Washington. "He's a political lightning rod because the department has been at the forefront of so much since 9/11."

"The Justice Department is often at the point end of the spear and it deals with national security issues and criminal justice issues and that are particularly salient in the policy environment. I do think Eric has been has caught a lot of the flak from that," says Jamie Gorelick, who served as Deputy Attorney General in the Clinton Justice Department and on the 9/11 Commission. Matthew Miller, who worked alongside Holder as his spokesman, notes that "people who once saw him as a career prosecutor now see him as the face of the Justice Department." That's certainly true and with the investigative machinery of the House in the hands of a Republican like Issa who is eager to use it makes life more difficult. But Holder's wounds can often be self-inflicted.

Holder was never going to stay through both terms. (Reno is the only attorney general in the country's history to stay that long.) And they say he'll be gone when Susan Rice and Samantha Power get settled in with John Kerry and Chuck Hagel and after James Comey is confirmed as the new FBI Director. There are not a lot of signs, though, that Holder will be able to finish on a high note. There's unlikely to be another high-five moment, a Supreme Court nomination or victory akin to health care. (The end of the Defense of Marriage Act which would be a victory but bring its own deluge of litigation.) What he needs most now are character witnesses who will talk up the work of the 110,000-plus employees of DOJ and Holder's own public service. One of them could be the outgoing FBI director.

In 1995, Holder, with the Rostenkowski case not too far in the rear-view mirror, got a call from Robert Mueller who had finished heading the Criminal Division of the Justice Department under the first President Bush and was in private practice in Boston and bored. The vaunted Republican called Holder just wanting a job working for him as a prosecutor. Holder was stunned. Mueller's job at the Department of Justice had been several levels higher than his. It's about equivalent to a recently retired executive vice president of say, Bank of America, calling the head of a local branch and asking for a job as a loan officer. "He and Eric developed a very close relationship," recalls Schertler who ran homicide cases under Holder at the U.S. Attorney's office and was Mueller's supervisor. It showed Mueller's love of prosecuting--but also his respect for Holder. That's the Eric Holder his friends tout but that was a long time ago.