From his improbably successful run for mayor in 2001 until now, Mike Bloomberg has leaned on three trusted aides: Kevin Sheekey, the ever-creative political strategist who gave the city the 2004 Republican National Convention and gave the world the abortive 2008 Bloomberg-for-president campaign; Ed Skyler, who rose from campaign press secretary to deputy mayor, overseeing a host of key agencies; and Patti Harris, Bloomberg’s loyal gatekeeper since 1994. Last month Sheekey quit, and last week Skyler left for a job at Citigroup. Only Harris remains, and she’s added big responsibilities outside of City Hall, running Bloomberg’s foundation.
Bloomberg, of course, has never lacked for confidence. Yet in his political career he’s been smart enough to know what he didn’t know, and Skyler and Sheekey proved invaluable guides and enablers—and were among the very few people in his world willing to stand up to him. In October 2009, Bloomberg was diffident in his first debate against Bill Thompson. His campaign team grew anxious, knowing that the race was tight and believing Bloomberg needed to attack in the next debate. So they turned to Skyler, a man who wasn’t officially part of the reelection effort but whom the mayor trusted completely, to prep Bloomberg and persuade him to come out punching.
Staff changes were expected, and desirable, for the third term, since it promises to be grueling. “Mike built a company that was designed to absorb the departure of people,” says Bill Cunningham, a political strategist who left after Bloomberg’s first term. “He’s taken that mentality into government. Mike is a systems kind of guy, an engineer, and he thinks in terms of boxes to fill and the results he wants to achieve.”
Yet Bloomberg’s management style will be tested by the recent departures. “The thing that they are going to find so hard to replace in Skyler is his ability to communicate with the mayor,” an insider says. “They will be able to find someone to move the nuts and bolts, but someone who has the ability to move the mayor on the most difficult discussions—that will be very, very, very hard to replace. Ed was the mayor’s compass. Mike had ideas about what he wanted to do, but Ed pointed the direction.”
Sheekey was the big thinker who pushed Bloomberg to pursue national issues like gun control and global warming. He isn’t going very far, taking a loosely defined job at Bloomberg the company. Former Hillary Clinton communications director Howard Wolfson, who helped run Bloomberg’s 2009 campaign, will assume Sheekey’s portfolio. “It’s unclear exactly where Howard is on the political spectrum, but he’s certainly pretty far left of Kevin, who is a centrist, Moynihan-type Democrat,” a business leader says. “It’s a concern among Mike’s corporate friends.”
The larger worry, for non-billionaire citizens, isn’t that Bloomberg will be unduly influenced—it’s that his mind will be impossible to change if the new staffers aren’t invested with real power. “If a great idea comes up, and the mayor is against it at the start, who is going to carry the water now that Sheekey, Skyler, and Dan Doctoroff are gone?” a City Hall insider asks. “The replacements are starting with limited ability or experience to get it done.” After eight years in office, Bloomberg, the once-proud amateur, has learned a great deal about the political game. But it’s a tough one to play all by yourself.