How Howard Wolfson went from Team Clinton to Team Bloomberg

May 20, 2013

The crash of Hillary Clinton's 2008 presidential campaign drastically changed political trajectories, sending people to unexpected and mostly impressive places. (Read the full piece on where the chips fell here.)


Howard Wolfson. AP Photo/CBS Face the Nation, Karin Cooper

But perhaps no one ended up in a more surprising place than Howard Wolfson, Clinton’s kamikaze (as Chris Matthews called him) and a lifelong Democratic warrior.

For starters, the urge to get away helped the famously flying-adverse Wolfson, who once bailed on his future wife at a British airport to take the QE2 ocean liner home, get over his fear. But it also helped him get over the Democratic Party.

As buzz builds for a 2016 Clinton campaign, it’s worth remembering that the 2008 experience was so searing for Wolfson that he found solace with Mr. Parties-Don’t-Matter himself, New York City Mayor Michael Bloomberg.

Here's a full accounting of how Wolfson became part of Team Bloomberg.

Wolfson's recruitment was handled by the mayor's right hand man, Kevin Sheekey,  over drinks at Kennedy’s, a pub on 57th street in Manhattan. Sheekey, knowing that Bloomberg was more vulnerable to losing a bid for a third term than most people in the city thought at the time, recounted how he sought to bring his potentially most dangerous enemy into the fold.

“Howard now that the campaign’s over, what are you going to do?” Sheekey asked Wolfson, who answered that he expected to go back to DC as a consultant.

“Howard you can’t go back to DC,” Sheekey said.

“Why not?” said Wolfson.

“Howard no one has said more negative things about the incoming African American president than you and I’m including John McCain.”

Wolfson paused and looked up at Sheekey.

“I think that might be right. So what are you saying?”

Sheekey pitched him on the idea of working on Bloomberg’s reelection campaign

Which, Sheekey argued, would open the door for him in anything he wanted to do in his hometown. Wolfson paused again and said to Sheekey, “you know, I’ve said a lot of negative things about Mike Bloomberg too.”

Sheekey asked what Howard thought of the mayor and Wolfson responded, “Mike Bloomberg has been a great mayor, and he should be reelected and the city needs him.”

“If you say that to that Mike Bloomberg,” Sheekey concluded. “We’re not going to have a problem.”

Wolfson is now the deputy mayor of New York City and the public face of the city's bike lanes.

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Ed O'Keefe | May 20, 2013