Jacob Gaylord

When Cheshire native Jake Gaylord graduated from Hoosac Valley High School in 2005, he couldn't find a landing spot for college that seemed to fit just right. After some hesitation, he enrolled at BCC, but being from a family of limited means, he had to pay for it himself. For a while, he made it work, taking classes while working about 70 hours a week at a liquor store in Pittsfield owned by the family of his girlfriend (now his wife). The son of two hard-working parents — his mom a schoolteacher and his dad a steelworker for over 40 years — the work ethic came naturally. But eventually, he couldn't make ends meet.

"BCC wasn't free like it is now. I just couldn't afford to go anymore. I couldn't afford the books. I couldn't afford the tuition. So, I had to make a decision," Jake recalls. "I quit in 2006, and I ended up enlisting in the National Guard because of the free college initiative."

Jake completed basic training in 2007 and eventually went on to serve in Afghanistan as a Combat Engineer for the 379th Engineer Company. Their mission included clearing minefields and unexploded ordnance. After serving almost six years in the Guard, Jake returned home to a scenario he did not expect.

"I could not find work once I came home from Afghanistan. No one would hire me. I couldn't even get a job in security," he says. He began working wherever he could find employment, including jobs in construction, paper mills and with family members. He was getting by, and life was looking up when his girlfriend Tawny said yes to his wedding proposal. But eventually, Jake realized he needed job security and upward mobility.

"It came to a point where I just felt like I could do more and do better. So, I ended up quitting my job a month before my wedding and went back to BCC in 2012 to finish my degree," he says. To his surprise, he learned he only had one semester left to complete his associate degree in criminal justice. In the meantime, he continued job-hunting, but the prospects were not exactly lining up. He and Tawny considered leaving the area to find better work.

Just when they were thinking about moving, Jake got a letter in the mail from the Berkshire County Sheriff's Office inviting him to try out for a physical test. He decided to take the plunge. Despite stiff competition with about 170 candidates, Jake was accepted.

"The final step was a sit-down with the sheriff, who is still the sheriff, Thomas Bowler. He was very honest with me," Jake remembers. "He said, ‘I don't care what names you have on your resume. I care what you're going to do for this facility and for your community.' So, I gave him the best spiel I possibly could, and I got hired in 2013. I've been here ever since."

As Jake prepared for training on the job, he was determined to finish his degree at BCC. Thanks to the help of professors like Reena Bucknell, Jake says, he got on the right path.

When I came back, I realized that going back to school at an older age can be really difficult. You lose that ability to learn stuff. But the professors really helped me out.

Jake graduated BCC in 2013, although he missed the commencement ceremony for an unusual reason. He was at the sheriff's training academy for "spray day," a required part of training in which trainees get sprayed with oleoresin capsicum, known as "OC," a type of pepper spray. With training behind him and an associate degree in criminal justice in hand, Jake was on his way.

"I took the opportunity at the sheriff's office because my goal was to use it as a stepping stone, but I'm still here. I've done so much," says Jake. "I wear 30 different hats at a time, but I love the work."

Jake started as a housing unit officer, overseeing the inmate population to ensure safety and security. Alternating between two incarceration units, he worked second shift from 3-11 p.m., overseeing a population of 40 to 50 inmates in each unit. That involved doing security rounds, making sure there were no altercations or fights, and answering inmates' questions.

"When you say ‘corrections officer,' a lot of people think, ‘lock them up and throw away the key,' but I can say that here in our facility, we act more as mentors," Jake says. "We are dealing with people we grew up with, people we know, people we're going to see out on the street. We hear their stories and try to offer some guidance." The job also involved collaborating with medical personnel, case management staff, religious service leaders and a number of treatment programs.

"We all collaborate to help these inmates. It's a huge team effort," says Jake, who held the position of pod officer for a number of years while also serving as a Correctional Emergency Response Team (CERT) officer. He was part of a group of highly trained individuals tasked with tracking inmates' movements in the facility, as well as responding to medical situations and "highly combative altercations."

In 2021, Jake was promoted to sergeant, staying on second shift and learning how to become a junior supervisor. Just a year later, he reached the rank of lieutenant, a position he still holds today, but his role is much different than when he started. After 12 years of being a second-shift officer, which Jake calls his "bread and butter," he realized he needed to make a change.

"I was warned not to lose touch with your family, because they're your biggest support system. Sadly, it was becoming very obvious with my two older sons that me not being home at night was taking a toll," Jake says. Now, he's working the day shift doing community engagement, public relations, recruiting and retention, and event coordination. It's a busy position, he says, but it was all worth it to be able to be home with his family.

In the 13 years since Jake joined the Berkshire County Sheriff's Office, he has accomplished more than he ever imagined he would. Aside from his basic job duties, he is a Peace Officer Standards and Training (POST) officer certified through the Commonwealth and serves on the Berkshire County Special Response Team (SRT).

"I thought I would only be here a few years. I've had other opportunities, but I really enjoy the atmosphere here. Maybe it's the military part of me, but the camaraderie is why I stayed," says Jake, who works side-by-side with military veterans. He also credits Sheriff Bowler for being not just a boss and a mentor, but also a friend.

"I would do anything for Sheriff Bowler. He's an amazing guy," says Jake, who recounts a poignant story. His twin sons Gage and Gavin were born early, and after spending time in the NICU in Baystate Hospital, he was still on leave when the family came home. The first person to call was the sheriff.

"He and his wife came with dinner for us. They stayed and hung out and ate with us," Jake says. And when third son Keegan was born three years later, the family had only been home for a couple of hours when the baby began having a medical emergency and had to be hospitalized at Baystate Hospital. Again, Sheriff Bowler and his wife came over to help.

"They took my twins outside and played with them, which allowed me to shower, eat, and catch my breath," Jake says. "He didn't need to do any of that."

It's that sense of empathy and collaboration that makes the job special, says Jake, and it makes him relate to the inmates more closely.

"Corrections isn't just supporting inmates here in the facility. Our role is also to support them on the outside and hopefully get them on the right path, because we don't want to see them come back to us," says Jake, who praises the Berkshire County employers who are willing to work with formerly incarcerated people and the hard work being done at Second Street Second Chances.

"So many times, people judge a book by its cover. As soon as they say, ‘I was formerly incarcerated,' they're labeled as that. They're not given a second chance," Jake says. "They made a mistake, but they have a family to feed and bills to pay, just like the rest of us. They just need a chance to be able to prove to people, that they can work a 9-to-5 job, that they can support their family."

Now that BCC provides free education, Jake says, things have changed. "It will create opportunities for people who are on the fence. BCC can be a great option, especially because you don't have to put that added financial stress on your family. You can go to college for free. You can follow your dreams and do what you want," he says. "I think that's one of the unique things about BCC. If you look around Berkshire County, there are so many successful businesspeople who started their education at BCC."

Today, Jake has a bachelor's degree in criminal justice he earned from Southern New Hampshire University, which he completed in three years while working evening shifts. The twin boys are turning seven and off to first grade, and the youngest son is now four and in Pre-K. His wife continues to be his biggest supporter.

"She sees the best in me and always pushes me to do more," Jake says. And, for now, doing more is exactly what he wants.