72 Minutes With Mark Penn
❧ Breaking down campaign strategy with the former Clinton Svengali turned Microsoft attack dog.

December 27, 2013
By Reid Cherlin

"I have five or six key lessons from politics,” says Mark Penn, the veteran pollster and adviser to both Clintons, in his glass-lined capital office, “and one of them is that you’ve got to be explaining who you are, what makes you unique, and what sets you apart.” Penn, 59, is known for what insiders call “contrast,” the kind of slashing, negative advertisement that can dig a candidate out from a fifteen-point hole. As the chief strategist on Hillary Clinton’s 2008 race, he was the man behind the “3 a.m. phone call” ad that helped tank Obama in the March primaries. He’s also the guy who not so subtly brought up Obama’s past cocaine use in a televised interview and whose sideline as a consultant for a foreign government got him dropped in the home stretch of Hillary’s campaign. Not that Penn spends much time revisiting those memories. “The only thing I would like to have changed was the outcome,” he says.

His Beltway profile suffered, but his reputation as a pugilist apparently did not. In July 2012, he signed on full-time as a strategist for the faltering Microsoft. The mission was to shake up the company’s long-standing reluctance to push back publicly against its rivals, Apple and Google, who have been eating up market share. In July, a month before Microsoft announced that CEO Steve Ballmer was on the way out, the company reorganized, putting Penn in charge of advertising, in addition to his strategy portfolio, signaling that Microsoft intended to fight at last. “Let’s understand that competitive is in our bag now,” he says as he reclines in his office chair. “People like brands that stand up and say, ‘Hey, no, no, no—let me show you what we do here’”...

Read on at New York Magazine ➝