“Down! One. Down! Two. Down! Three.”
Michael Wynn paused, arms extended, waiting for the next order telling him to lower his body to the floor. He had survived his plebe year at the US Naval Academy, but graduation was still a long way off. Like most of his class, Wynn had arrived at Navy convinced that aviation was the only path for him. The movie Top Gun had come out two years before, and every Navy recruit was lining up to become the next Maverick.
As he dropped again and strained to raise his body off the floor, the upperclassmen hovering over him suggested a new path. Wynn was a short ex-wrestler with bad eyes. He stood little chance of winning the ultra competitive race for aviation. Instead, the upperclassmen told him, his background as a boy scout made him perfect for the Marines.
Aware of the fact that life commanding 12 grunts required more communication training, Wynn switched his major from the sciences to English. Shortly after that, he went home to Pittsfield, took some courses at Berkshire Community College, and transferred to Williams to focus more fully on the liberal arts.
After an injury ended his military career and poor eyesight kept him out of the federal law enforcement agencies, Wynn settled on a career as a police officer in his hometown. Fourteen years after his college graduation, Wynn became one of the youngest police chiefs in Pittsfield history.
I met up with Wynn in his Pittsfield office to learn about his journey into law enforcement and day-to-day life as a cop.
How did you end up deciding to become a police officer?
I arrived at Williams as an officer candidate in the Marine Reserves so I thought I already knew what I was going to do when I graduated. Unfortunately, the next summer, when I was at Quantico training, I was injured, and I was discharged from the Marines.
When I got back to Williams for my junior year, I had to come up with an alternative plan. I visited a mentor from Navy who was working for the DEA, running the training programs for agents who went to South America to go after drug labs. It wasn’t the Marines, but it sounded pretty cool.
Right as I was getting ready to graduate, however, there was a period where there was no federal budget. The only people the agencies would take were prior military and prior law enforcement. So I graduated and came back to Pittsfield.
The Pittsfield police department was expanding their community police programs, and I applied to work as a civilian in the department. The first job I had was recruiting minority applicants to join the force. As part of that, I took the officer test myself and was selected for a position a year later.
I still thought I was going to go the federal route. My eyes weren’t great so I couldn’t work for the secret service or the border patrol. I got to the finals of the DEA, but that didn’t work out. After that, I realized that I’d been in Pittsfield for a full year and the department had taken pretty good care of me. I had a conversation with my commander at the time. They decided to send me away to become a trainer.
I stuck around and was fortunate enough to be promoted rapidly a couple of times. Then in 2007, my chief retired, and they needed a replacement, and I got a chance to take over the department.
Is there a moment when you knew that you wanted to do law enforcement type service?
I was very active in boy scouts. I happened to be in a scout troop where 30% of the adult leaders were retired military. They saw something in me, and I was groomed from a very young age to at least consider the possibility of an officer’s career.
When I lost that opportunity after I got hurt at Quantico, I was rudderless—I didn’t know what I was going to do. If my mentor hadn’t reached out and said, “It’s not the end of the world—you can take that energy and apply it to a different type of service,” I’d probably be driving a truck now.
How did the Williams education help your career?
I don’t care what you want to do with your life—there are certain things you need to be able to do. You need to be able to think critically. You need to be able to be self aware and introspective. You need to be able to communicate clearly both verbally and in writing. You need to be able to access information quickly and analyze it. You need to be able to network. Williams makes sure you have those skills.
Are there any moments that stand out in your mind where you’re thankful for coming home and dedicating your life to police work in your hometown?
Oh yeah, lots of them. I can’t count the number of times where I responded to a call as an officer, and I knew the people and was able to respond to them personally in addition to professionally. Sometimes those are horrible calls and all you can do is say you’re sorry and be there for them. Sometimes they’re calls that we win, and we can say, “We took care of it for you.”
What advice would you give to Williams students preparing for life after graduation?
Find your passion and stick to that. If you want to work in a smaller community and work one on one with people, you might not get rich monetarily, but you’ll benefit in other ways.
The other thing is: be open to new experiences and understand that you can only control what you can control. There are outside influences like my injury that no amount of planning in the world can account for. If you only have one plan like I did, it’s damaging. Control what you can control but be willing to be flexible and roll with the punches because they’re coming. With a Williams education you should always be able to dust yourself off and get back in the game.