Barack Obama has a tough dilemma. If he staffs his administration with talented outsiders, he satisifies citizen demand for “change,” but the problem is that outsiders don’t have a clue about how to govern in Washington (case in point: Jimmy Carter’s 1977 Georgia team). Yet if Obama staffs his administration with insiders who do know how to govern (clearly, his chosen option), he undercuts his “change” mantra – mostly because so many of those insiders logged time with the Clintons, and, on occasion, became soiled by the association.

Case in point: Eric Holder, who reportedly has been tapped to become the nation’s first black attorney general.

On balance, Holder, the deputy attorney general under Bill Clinton from 1997 to 2001, may well be a fine pick. A former judge (appointed by Ronald Reagan), and prosecutor, he is lauded by Republicans as well as Democrats. He’s a tough-on-crime guy who wins praise from prosecutors and police. He is naturally being assailed by both liberal commentators (one of whom says that Holder’s post-9/11 remarks sounded “as if he had just stepped out of the Bush camp”), and by conservative commentators (one of whom calls Holder “a conventional, check-the-boxes creature of the Left”) – and, frankly, I consider that kind of pan-ideological scorn to be a compliment.

But he’s also a prime example of how tough it is to work for the Clintons without getting mucked in the process. Nearly a decade later, he is still trying to scrub himself clean.

The lesser known incident occurred in the summer of 1999, when President Clinton commuted the sentences of 16 convicted Puerto Rican terrorists who had been responsible for six deaths and dozens of injuries in more than 100 bombings on U.S. soil between 1974 and 1983. Call it a sheer coincidence, but it just so happened that, at the time of Bill Clinton’s decision, Hillary Clinton was busy mapping a Senate bid that would require major support from New York’s populous Puerto Rican community.

Bill acted in defiance of opposition from the FBI, the Bureau of Prisons, federal prosecutors, and a number of senior Democrats. But his Justice Department didn’t give him any grief; indeed, as the press reported at the time, deputy attorney general Holder supported the clemency option.

More notorious, of course, was the Marc Rich affair. As Clinton was heading out the door in January 2001, he granted a pardon to an unrepentant fugitive crook who was being sought on fraud and racketeering charges, not to mention trading with the enemy. At the time, Rich’s own biographer called him “the most wanted white-collar criminal in America.” Call it sheer coincidence, but it just so happened that Rich’s ex-wife had been a generous donor to the Clinton presidential library and Clinton legal defense fund.

(I remember, at the time, speaking with a distressed Democratic strategist who said, “It’s hard to defend what appears to be indefensible. The pardon was a bad call, and this is a bad story for us.” That was David Axelrod, known today as Obama’s genius strategist.)

Anyway, back in that winter of ’01, Eric Holder was required to sign off on his boss’ brainstorm, and he did so – by paying it minimal attention. As Holder confessed in 2001 congressional testimony, “Some bells should have gone off, some lights should have gone on…If I’d known, obviously, that it was going to turn out this way, I mean, I certainly wouild have done things differently…I wish that I had assured that the Department of Justice was more fully informed and involved in this pardon process.”

And something else happened on the day Rich was pardoned. Clinton commuted the sentences of two Weather Underground bombers, Susan Rosenberg and Linda Sue Evans. Seven years later – at a Democratic debate in April 2008 – candidate Obama assailed that Clinton decision. What’s ironic, however, is that Obama’s choice for attorney general signed off on that Clinton decision.

Really, these Clinton entanglements seem endless; perhaps “change” is partly about the opportunity to start afresh. If Eric Holder ultimately becomes attorney general, no doubt he will hope that F. Scott Fitzgerald was wrong when the novelist insisted that there are no second acts in American lives.