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Christopher Cipolla, 29

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If you think one job is tough, try tackling Christopher Cipolla’s legal-profession trifecta: the Harrison native operates a private practice specializing in real estate law; is the Harrison Deputy Village Attorney (appointed by Harrison Mayor Ron Belmont in 2012); and a principal in Excalibur Sports, Inc., where he handles salary arbitration for Major League Baseball teams like the Atlanta Braves, Cincinnati Reds, and Minnesota Twins. Cipolla enjoys the triple challenge. 

“I typically divide my time between my practice and the Village, and, from December to February, I add in the stress of salary arbitration. I end up apologizing to everyone in March after I’ve become my normal, pleasant self again,” he jokes. 

Cipolla’s duties for Harrison include leading collective-bargaining negotiations with the Village’s unions, including the Teamsters and the Civil Service Employees Association (CSEA). He counts as one of his proudest moments shepherding the recent agreement with the Teamsters, who had been working without a contract for three years. “I grew up in Harrison and I know a lot of the people I was negotiating with, so it was great to come to an agreement,” says Cipolla, the town’s youngest-ever deputy Village attorney appointee. 

The sports nut, who received his JD from New York Law School (2009) and a BA from the University of Maryland, College Park (2006), also relishes his Excalibur role—including the occasional chance to interact with sports legends. When he interned for Excalibur during law school, his very first hearing involved famed agent Scott Boras, who was representing MLB star Felipe Lopez. (Excalibur won the case.)

Cipolla’s winning philosophy? It’s simple, he says: “I work constantly, and I make myself very accessible.”