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Who

Mayor Michael Bloomberg's former press secretary, Skyler is now the deputy mayor for operations. He's the youngest deputy mayor in the city's history.

Backstory

Skyler got his start in municipal governance early, interning for the City Council in high school and taking a $22,000-a-year gig at the Parks Department after graduating from UPenn in 1995. He later moved to City Hall to work in Rudy Giuliani's press office; when Giuliani declined to run for Senate in 2000, Skyler headed off to the private sector, working in the corporate communications department at Bloomberg LP where, lo and behold, he found himself swept up in mayoral politics anew. When Michael Bloomberg officially declared himself a candidate in May 2001, he recruited Skyler to his press team, naming him press secretary after his victory and then communications director after the departure of Bill Cunningham. In 2006, the precocious Skyler's dramatic rise continued apace when he was promoted to deputy mayor for administration, becoming the city's youngest deputy mayor in history. In 2007, Bloomberg bumped him up yet another notch, to deputy mayor for operations.

On the job

Skyler is one of the select few with access to the mayor, and has a reputation as one of Bloomberg's fiercest defenders; as press secretary, he was often described as the mayor's "pit bull press secretary" for his protective ways. His unwavering loyalty has earned him high marks with his boss in the City Hall bullpen, and Bloomberg has repaid Skyler's devotion by expanding his responsibilities. Now the city's deputy mayor of operations, Skyler helps manage a number of the city's uniformed departments (like the police and fire departments) and directly oversees a handful of agencies including the Department of Sanitation (headed by John Doherty), the Taxi and Limousine Commission (headed by Matthew Daus), the Department of Transportation (headed by Janette Sadik-Khan) and the Department of Citywide Administrative Services (led by Martha Hirst).

Keeping score

Skyler made $188,304 in 2007.

Drama

Skyler's hard-charging style occasionally rubs people the wrong way. He offended off-duty police officers by dubbing them "thugs" for showing up at Bloomberg's public events to complain about contract negotiations. In 2002, he got into an argument on Thanksgiving Day with Andrew Kirtzman, a reporter for WCBS. After Kirtzman asked the mayor a combative question, Skyler got offended and a shouting match ensued, with Skyler telling Kirtzman to "go fuck yourself." The mayor stood by, looking embarrassed.

Personal

When the handsome, 6'4" Skyler was asked what it was like to be named one of the city's most eligible bachelors by the New York Post, he admitted he didn't have much time to take advantage of the designation. His bachelor pad is a 1-bedroom apartment in Andre Balazs' Kenmare Square building, which he paid $925,000 for in 2006.