Kevin Sylvester '14

Love What You Do

Chief of Police with the Ossining Police Department, Kevin Sylvester’s path to law school was not on the straight and narrow. After being kicked out of college, Kevin took time to reflect on what path he wanted both his life and career to take. From the Marine Corps to becoming a police officer to having his first child during his second year of law school, Kevin’s journey to where he is today has been nothing short of interesting and a true display of determination.

Did you go straight to law school from undergrad?

I got kicked out of college the first time I attended. It wasn’t that I was having too much fun. I was just an immature kid who was probably depressed and unprepared for living independently and studying full time. I stopped going to class and I left there with lots of credits, but no direction. It was the best thing that ever happened to me because it allowed me to reset and find my fire. I thank god I didn’t scrape by and finish because I’d probably be stuck in a job I hate, doing something that bores me. After leaving school, I joined the Marine Corps and then the police department.

With a police and military background, what made you decide to go to law school?

I always wanted to go to law school. Though most people finish high school, go to college, and directly to law school, I wasn’t ready for that. I didn’t finish my undergraduate program until I was 30. By that time I was working overnight shifts in a police department. Police officers in New York can retire after twenty years so I figured a law degree would give me the opportunity to retire and work a more “normal” schedule.

Do you remember your first day at Haub Law?

Absolutely. Most of the students were nervous but I’d been through so much. Many people feel an obligation to perform when they get to law school, but I already had a good job. I knew I didn’t HAVE to be here. I could have walked out at any time. I was here because I wanted to be here. I chose to be here. It’s a completely different perspective and really allowed me to enjoy my time here. I met some of my best friends that day. Hi Kaitlyn!

What were some of your biggest struggles during law school?

My son was born the first week of my 2L year. If you ever thought law school was tough, imagine reading cases in the delivery room! That’s not even an exaggeration. Nothing in law school came natural to me. I had to work hard and grind. When my son was born, I was terrified I would fall behind and never catch up so his first book was Contracts: Cases and Doctrine.

Looking back, what do you miss most about law school?

I live for the challenges. I truly miss the long days and nights of studying in the library. Even though we were stressed out and felt a ton of pressure, we did it together. It may have been difficult but I have really fond memories of the nights we locked in to prepare for exams, loaded with snacks, together with friends. I really appreciated the opportunity to work with so many incredibly smart students who went on to be wildly successful attorneys. I keep in touch with many of my former classmates. Networking is everything in this business. My alumni network is where I go for professional advice, for friendship, and for motivation.

Moving on to present day, you are the police chief for Ossining—what is your day-to-day like?

During orientation at Haub Law we visited Cuddy + Feder LLP and the managing partner, Chris Fisher, was asked, “as a partner, what is your day like.” His response changed my life. He said, “I’m a business owner—my day is from when I open my eyes to when I close my eyes.” That moment changed my life. I want to spend my time working on projects I believe in. When I know my energy is benefiting others, I never want to stop. My work day now really is when I open my eyes (around 5:00am) until I close my eyes (around 10:00pm). People rely on me to keep them safe, to help raise their children, and to keep them informed. If done right, it’s a heavy burden and the work never really ends.

What is most rewarding about your job?

I love making people smile. Sometimes it’s speaking with their kids and sometimes it’s offering comfort in a difficult situation or with clients I might help them solve a complex problem. I really appreciate having the opportunity to help people better understand their world. I want to give people something to believe in.

Do you also maintain a law practice?

I started slow, but my practice is growing. I have a solo firm, supported by quite a few alumni who have taught me everything. Most of my work is transactional real estate work but I’m branching out and learning new things every day.

What are some of your passions aside from law enforcement?

This is the hardest question because I love to love things. I coach my kids in little league and I’m a huge fan of youth baseball. I love winter sports and recently switched from skiing to snowboarding. I love endurance sports—distance running, triathlon, anything except the obstacle course races. Those aren’t for me. I love spending time with my kids and my dog, but when I go to bed at night, I can’t wait to get to work in the morning because I forever have something exciting I want to work on.

They say if you love what you do you’ll never work a day in your life. That’s a lie. I work… a lot. But I love what I do so I don’t mind long hours. The thing I learned through the military, policing, and a legal career, is to spend your time doing things you can believe in because it makes it all worthwhile.

Had you not followed the path of law enforcement what do you think you would be doing?

I think policing saved me. It taught me so much about life and community. I’m afraid to think of what I’d have become without all the people I met throughout my career.

What is some of the best advice you personally have received?

One of my mentors told me that my debt for all her guidance was to pass it on. For all the good experiences I’ve had and all the support I’ve received, it’s my turn to pay it forward. My story might not resonate with everyone but I bet there are a couple of students still trying to find their “why.” If that’s you, let me know. A cold call may feel weird but I can’t count the number of friends I’ve made by reaching out to people who inspired me and making a connection.