Who Is Cliff Sloan, Obama’s Pick to Close Guantanamo Bay?

News that President Obama selected Skadden partner Cliff Sloan as the State Department’s special envoy to shut down Guantanamo Bay was, at first, surprising.

Sloan is an esteemed Washington lawyer with diverse government and private sector experience—but he’s not known as a national security attorney. He’s probably best known as a legal expert on media and cyberspace. Before joining Skadden in 2008, he was publisher of Slate magazine and general counsel of Washingtonpost.Newsweek Interactive, the Post’s online subsidiary. He’s taught courses on cyberspace to law students at Georgetown, George Washington University, and American University.

Further bolstering his reputation as media savvy are the several appearances he’s made on Comedy Central’s The Colbert Report, including a two-part segment where Sloan “vetted” Colbert for a possible appointment to the Obama administration. Watch Part 1 and Part 2.

But Sloan is also a constitutional expert, having co-written a book about the landmark Marbury v. Madison case, The Great Decision: Jefferson, Adams, Marshall, and the Battle for the Supreme Court. And The Colbert Report appearances show something else about him: Sloan is an affable guy. Likability and a reverence for the Constitution are no doubt required for anyone to have even the slightest shot at untangling the massive legal mess that is Gitmo.

Sloan is indeed charming in person, and his past experience working with stalwarts of both the right and the left show that he’s capable of ascending partisan politics. Sloan served in the Clinton White House as associate counsel to the president, and clerked at the Supreme Court for liberal-leaning Justice John Paul Stevens. But he was also an assistant to US Solicitor General Kenneth Starr during the George H.W. Bush administration.

Obama obviously needs a coalition-builder for this particular job—Republicans in Congress have previously blocked the White House’s efforts to close the prison, and just this month, House Republicans proposed legislation that would keep Guantanamo
open.

When considering Sloan’s track record navigating both sides of the political spectrum, it’s actually not so surprising the President looked to him. Whether the strategy works is another question.

The administration certainly hopes it will, and it has already begun hyping Sloan’s bipartisan cred, collecting statements from his wide variety of supporters. In written testimonials about Sloan, retired Justice Stevens said he is “fully capable of performing the most difficult assignments, including the one that the President has wisely selected him to undertake.” Starr called him “an admired and gracious friend” and a lawyer with “enormous ability and complete integrity.”

Fred Fielding, White House counsel to George W. Bush, said “Cliff possesses the requisite gravitas, imaginative intellect, and tactful perseverance” required for the job, and called Sloan’s selection by Obama “a wise choice.”

Secretary of State John Kerry, a friend of Sloan’s for a decade, also emphasized in a statement that Sloan’s “intellect and skill as a negotiator is respected across party lines.”

Marisa M. Kashino

Senior Editor

Marisa M. Kashino joined Washingtonian in 2009 and was a senior editor until 2022.