“New York has better playgrounds than any city you will ever visit,” he said. “Everywhere you go, in any borough, there are great playgrounds here. D.C. doesn’t have any. The jungle gyms are much better here, too. It is a great place for little kids.”
Sheekey is well versed in the similarly rough-and-tumble world of big-city politics as well. Perhaps the experience will help in his current position as campaign manager for New York City Mayor Michael Bloomberg, who is running for reelection this year.
“He is running as a Republican in a Democrat town,” admitted Sheekey, who is not shy at all about touting his Democratic bona fides himself. He knows he may have a tough sell at hand, despite the mayor’s incumbency.
Sheekey is quick to praise Bloomberg’s first term, when he took the reins of a numbed city less than a month after the Sept. 11 attacks.
Sheekey, who’s 37, had been working in the capital for Bloomberg L.P., the mayor’s financial information services company, for two years when he was tapped to be an advisor for Bloomberg’s first race. The millionaire had been mulling a run at office, and Sheekey’s political savvy was just what he needed.
Sheekey’s parents grew up across the Hudson in Union City and Jersey City and were involved in politics. His paternal grandfather worked for Jersey City’s notorious Mayor Hague of “I am the law!” fame.
Along with his wife, Robin, whom he met in the first grade, Sheekey remained in D.C. after joining the Bloomberg campaign and commuted to New York on weekends.
Sheekey remembers assuring his wife that there was no way Bloomberg would win the election, and life would soon return to normal. It was hardly the case, however, and the situation was only complicated further when the couple became parents a week after the Sept. 11 attacks. The family picked up and moved to Manhattan.
“I tried to keep her calm,” he said of his wife. “D.C. is a very livable city, but there is no place in the world like New York.”
He recounts a famous line about Washington having “Southern sophistication and Northern charm.”
‘The worst of both worlds,” he said, laughing.
Upon arriving in New York for the first Bloomberg campaign, Sheekey quickly found that politics is no easier here than in his hometown.
“New York is a lot of things: it’s exciting, it’s diverse,” he said. “But I would never say New York is easy.”
While the couple’s twins, Samantha Ryan and Dillon Arthur, enjoy all that the city has to offer, their father is working on securing the mayor’s position for another four years.
It was his time spent in Washington that gave Sheekey the experience to run a big-city campaign, where he worked for Queens Rep. James Scheuer for 10 years and then with the late Sen. Patrick Moynihan.
After graduating Washington University in St. Louis, Sheekey said, he “started out as a receptionist and battled through promotions to get to Scheuer’s chief of staff, and then moved on to Moynihan’s office and battle promotions to get to chief of staff.”
After a considerable amount of time on the Hill, Sheekey thought the private sector was the way to go.
“I wanted to leave, and get out of politics,” he said. “I’ve failed miserably,” he added, laughing.
Luckily, he’s well prepared for his new assignment. He got a crash course in New York and politics, as well as the often contentious relationship between the two, while president of last summer’s Republican National Convention’s Host Committee.
“What did that teach me? Well, I learned how to put on an $85 million, four-day event,” he said. “New York City is the only place you could have done it.”
“I got to meet a sitting president, and witness a nomination. I had a front row to history.”
The Democrat first became chummy with Republicans while working in Washington, but said he takes care not to be drawn into the fray between parties.
“My background is not a partisan background,” he said, crediting Moynihan’s diplomacy in helping him handle partisan issues.
“Moynihan was not a democrat with a capital D. When I worked on Capitol Hill, I often had better relationships with Republicans than I did with Democrats because of the senator, and who he was.
“Public life was something [Moynihan] was raised to do. He was able to solve problems decades before anyone knew about them.”
While there are few surface similarities between the late senator and the mayor, honesty is a one common thread Sheekey has noticed.
Sheekey tells proudly of how Moynihan was the only Democrat willing to suggest that then-president Clinton should be investigated over the Whitewater scandal.
“Who else would say that?” he asked. “It was typical Moynihan — he’s not going to lie.”
Sheekey said he feels Bloomberg and Moynihan also “share an honesty that transcends politics.”
As far as his own politics, Sheekey doesn’t shy away from a difficult stand of his own.
“I guess I like it uncomfortably in the middle,” he mused. “It is much more difficult to run in the middle — I call it the honest middle.”
He will say, however, that “after 18 years, I am vowing this will be the last. After this I am going out to make an honest living.”
Sheekey said it was the importance of this coming mayoral election that kept him on board.
“The message is finding how we as a city continue to march forward,” he said. “Sometimes you love New York in spite of yourself. And you live here because you really want to.”