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Who

One of the mayor's closest confidantes, Sheekey is Michael Bloomberg's Deputy Mayor for Intergovernmental Relations, a roost from which he served as chief cheerleader for a Bloomberg presidential bid up until early 2008.

Backstory

A native of the D.C. area and a lifelong Democrat—his father worked at the Department of Education during the Carter administration, his mother was affiliated with the liberal advocacy group Common Cause—Sheekey went to college at Washington University in St. Louis, and spent the first half of the '90s working for Senator Daniel Patrick Moynihan. In 1997 Michael Bloomberg hired Sheekey to serve as chief Washington lobbyist for his growing financial media empire; along with fellow Bloomberg LP employee Patti Harris, Sheekey soon became one of Bloomberg's closest advisors.

When Bloomberg decided to run for Mayor a few years later, he tapped Sheekey, then in just his mid-30s, to run the campaign. With no shortage of cash on his side (Bloomberg put up some $74 million to finance his mayoral bid), Sheekey helped secure an improbable victory over Mark Green and subsequently joined the administration. In 2003 he left to help plan the Republican National Convention on behalf of Bloomberg; despite talk that Sheekey planned to move to the lucrative business of political consulting and assist with Arnold Schwarzenegger's campaign, Bloomberg persuaded him to return in 2005 for his mayoral reelection, which he rode to an easy victory. In 2006, the mayor tapped Sheekey for the newly created post of deputy mayor for government affairs.

Of note

Although his job title is vague, Sheekey's assignment is broad, and Bloomberg looks to him for advice on matters both large and small. He's helped architect the Mayor's center-left positions on hot-button issues of national import, like gun control. Sheekey was also tasked with building political bridges for Bloomberg across town and with cultivating relationships with various unions and special-interest groups.

But he's gained the most attention for relentlessly advancing the notion of a Bloomberg campaign for president. Sheekey floated trial balloons in the press while Bloomberg played coy with reporters; he oversaw a research team that analyzed the requirements for getting on the ballots in every state, identified areas in the country where Bloomberg would perform best, and assessed just how much the whole shebang would cost. Although Bloomberg ultimately decided against a run, Sheekey still emerged from the aborted campaign a victor: Just the talk of a bid substantially raised his own profile, which he'll no doubt parlay into a sweet assignment when Bloomberg's mayoral term expires, or perhaps even before then.

Keeping score

Sheekey made $196,574 from the city in 2007. He earned more than $700,000 for managing Bloomberg for Mayor in 2005, which made him one of the highest-paid campaign managers in American history.

Personal

Sheekey and his wife Robin live on Central Park West with their twin daughters, Dillon and Samantha. They live in the same building as Robin Hood Foundation head David Saltzman.

No joke

Sheekey is so hard to get in contact with that the mayor's staff gave him a cell phone solely for calls from Bloomberg himself. Sheekey calls it the "bat phone."