21 Most Intriguing: Cliff Sloan

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Publisher, Slate.com

Challenge this motion if you can: Cliff Sloan, publisher of the digital journalism juggernaut Slate.com, is the only person in the publishing industry who clerked for a Chief Justice (John Stevens) and argued five cases in the Supreme Court. Make an objection to that generalization if you want—he graduated from Harvard Law, so chances are he could argue you under the table.

But Sloan’s “Your Honor” days are over; he has traded his legal jargon for that of the digital publishing world, which he joined in 2000 when he became the Senior Counselor of Washington Post/Newsweek Interactive. Not long after that, the group acquired Slate.com, and he was the not-so-obvious choice for the top position. Sloan took it and never looked back, and what a wild ride it’s been. After all, he endured the dot-com bubble’s historic burst and still guided the online magazine to the pinnacle of its category. And with blogs and other magazines’ Web portals nipping at his heels, he keeps ahead of the competition with innovations such as the just-launched video magazine Slate V.

If that’s not enough intriguing-ness for one man, how about that James Bond caliber name to get a conversation started? But apparently being named Clifford isn’t all fun and games, especially when you share your moniker with a big red cartoon canine.

“Apparently there’s a Clifford the Big Red Dog book for every stage of your life,” he says.

Playground initiations can be so cruel, but Sloan can certainly claim rights to the last laugh.


Message Board

Jonathan Alter, Columnist and Editor, Newsweek
We were roommates at Harvard for three years and remain close friends. Cliff has always been whip-smart, ebullient and a lot of fun to be around. He was also more popular with girls than the rest of us. When we were all living in Washington in the early 1980s, my wife and I introduced Cliff to [now-wife] Mary Lou. It was kind of like that 1970s' sitcom, "Bridget Loves Bernie" - Irish-Catholic girl marries Jewish guy, except with Justice John Paul Stevens in attendance. Cliff is still exactly the same, only with less hair.

Eliot Spitzer, Governor of New York
Cliff and I became fast friends in law school, and we remain close friends to this day. He is, without a doubt, one of the smartest, most incisive thinkers of our generation. But I do remember this time in school when we were out jogging together, and for some reason he ended up running into a tree. That evening was spent in the emergency room. But really, he deserves every affirmative adjective out there.


What have you done this year?

  • Organized the second annual Slate 60 Conference on Innovative Philanthropy at the Clinton Presidential Library, honoring the world’s top philanthropists with President Clinton and other leaders in philanthropy.
  • Saw my two daughters’ high school softball team win their league championship, with my daughters as two-thirds of the
  • starting outfield.
  • Heard Van Morrison sing and jam at a small private concert following the Oscar Wilde Awards in LA at an event hosted by
  • the US-Ireland Alliance (my wife’s organization).
  • Oversaw the launch of Slate V, a new online video magazine from Slate.
  • Arranged for Slate the first-ever Presidential candidate mash-up with discussions with all Democratic candidates on September 12, to be hosted by Slate, The Huffington Post, and Yahoo!
  • Joined one of my closest friends as he was sworn in as Governor of New York.
  •  Worked on my forthcoming book (with my co-author David McKean) about the fight between Thomas Jefferson and John Adams that led to the case creating the modern Supreme Court.
  • Tried to train a new puppy with my 13-year- old son (unsuccessfully).

Playing Favorites

  • Food: Anything Indian; anything spicy
  • Music: Eva Cassidy, Kiff Gallagher, Maura O’Connell, Louis Armstrong, U2, Van Morrison, Ledisi
  • Web site: theonion.com, huffingtonpost.com, Scotusblog.com, mlb.com
  • Must-read Book(s): Anything by Philip Roth, Wallace Stegner's Crossing To Safety, Kazuo Ishiguro's Never Let Me Go, Michael Lewis' Moneyball, Jean Edward Smith's John Marshall, Jonathan Alter's The Defining Moment
  • Magazine(s): The New Yorker, The Atlantic
  • Must-watch TV: The Wire, The Office, 24, The Colbert Report , any Cubs game
  • Must-watch Movies: The Imposters, Napoleon Dynamite, anything with Susan Sarandon in it
  • Desert Island CDs: Eva Cassidy, “Live At Blues Alley”, Kiff Gallager, “Will and Surrender”, Van Morrison, "Pay The Devil" U2, "How To Dismantle An Atomic Bomb" Ella Fitzgerald, "Pure Ella", Harry Potter CD’s narrated by Jim Dale
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