The Bloomberg Whisperer

Michael Bloomberg has been running for president for barely three months. But his campaign manager, Kevin Sheekey, has been running for president for him for the better part of 15 years.

After Bloomberg won reelection as New York City’s mayor in 2005, a group of his senior aides went out to dinner to celebrate; “Kevin just started talking about the next campaign, and it was a presidential campaign,” Bill Cunningham, one of those present, told me. Three years later, Bloomberg himself seriously considered a presidential race, but when a reporter asked him about that flirtation after he decided to seek a third term as mayor instead, his answer was a sly deflection. “Kevin ran for president,” a smiling Bloomberg insisted, as Sheekey looked on with the barest hint of a smirk in the ceremonial Blue Room of city hall. “I didn’t run for president.”

Now Bloomberg is running for the White House in earnest, pushing the limits of what Sheekey himself once wryly called the “Sheekey Master Plan” for a Bloomberg presidency. Perhaps even more, Bloomberg is pushing the limits of what even the most talented staffer can do with a principal who is anything but a natural star.

The verdict is mixed. The campaign’s start burnished Sheekey’s reputation as one of the sharpest political minds of his generation: The unorthodox decision to skip the early-voting states gave way to a multimillion-dollar barrage of national television ads, hundreds of paid on-the-ground field