Unleashed From City Hall, Kevin Sheekey More Free to Fight Bloomberg Battles

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Big money, September 11, and Mark Green’s stumbles were the keys to Mike Bloomberg’s huge upset win in the 2001 mayoral race. But it was Kevin Sheekey who knew how to successfully combine those elements on behalf of a political rookie. Nine years, two City Hall terms, and one shadow presidential bid later, Bloomberg — who has never exactly lacked for confidence — is a whole lot more sure of his own political instincts and skills, and Sheekey has wearied of the nuts and bolts of budget negotiations with the City Council. Other politicians had been trying to lure Sheekey to run their campaigns, so today the mayor gave him the Bloomberg-world equivalent of a golden parachute, a lucrative job at Bloomberg LP. The move is being couched in the usual blah blah about the value of fresh faces for Bloomberg’s third term, but there are a number of other, more intriguing ramifications.

In late January, the mayor invented a vague City Hall job for Howard Wolfson, the Hillary Clinton consigliere who helped run Bloomberg’s surprisingly close reelection campaign. Wolfson and Sheekey agree on many things, but it was always difficult to see two such large personalities co-existing in close proximity. Wolfson, who is married to Nancy Pelosi’s chief of staff, will now assume responsibility for the part of Sheekey’s portfolio for which he never got enough credit — dealing with other elected players, especially in Albany — but Wolfson will also become Bloomberg’s day-to-day political strategist.

Sheekey’s new job at “the company” is supposed to include similar government-relations tasks. The biggest opportunity, though, may be in the reams of raw political data, from the awarding of government contracts to electoral demographics, that Bloomberg LP has been amassing. Sheekey will try to figure out how to shape that information into a marketable commodity — or into a valuable resource for a well-heeled candidate. One advantage to going private is that whatever he’s up to will become harder to determine.

Sheekey was plenty elusive and cryptic as a deputy mayor, but he was a city employee, subject to basic disclosure requirements. He now has even greater freedom to lay the groundwork for Bloomberg ’12, should President Obama continue to disappoint and Sarah Palin somehow become the Republican nominee. But even if the White House play never materializes, Sheekey will have more room to explore other political opportunities that might benefit Bloomberg and the city, such as backing vulnerable U.S. Senate candidates this fall.

As much good as Sheekey did for Bloomberg, and as trusted an adviser as he became, there have lately been tense moments in the relationship. When the mayor gave up on a 2008 presidential bid, he took out his frustration by crankily and publicly blaming Sheekey for the speculation. Last year Sheekey, among others, made little secret of his opinion that Bloomberg shouldn’t run for a third term, though he became a staunch soldier in the battle to rewrite term limits.

Sheekey always credits Bloomberg for encouraging him to “think big thoughts,” but the dynamic often worked the other way around, with the operative supplying not just clever ideas but the tactics to implement them. Sheekey enjoys the political game more than anyone in the mayor’s inner circle, so it’s unlikely he’ll go away completely. But Bloomberg is sure to miss him.