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One of Richford’s “Seven Saplings,” Jake Cunningham is becoming Colchester’s newest police officer

Written by
VSAC Staff

April 11, 2024


Jacob Cunningham and family

Jake Cunningham has had a lot of claims to fame.

He grew up in Wasilla, Alaska, in the same town as former Governor and Vice President candidate Sarah Palin. She famously said she could “see Russia from her house”; Jake saw her (and her paparazzi) every now and then at Wal-Mart.

After moving to Richford, Vermont, at age 12, he and his siblings were well-known as the family of seven kids who are Asian in the mostly white Richford schools. Nervous at first that they might be teased, the “kids from Alaska” instead got the last laugh; they convinced their classmates they used to live in an igloo and keep penguins. (Jake credits his older sister Amanda for dreaming up that joke.)

As a pitching star on Richford High School’s baseball team, Jake was named Division 3 Player of the Year, named to First Team All-State, and nominated for the North-South baseball game in 2016. (If you don’t recall a Jake Cunningham during that time period, it might be because everyone called him “Moose.”)

And on the unfortunate side, Jake was one of the first people to contract Covid-19 when he was in college—something that kept him down and out for a while, but that ultimately didn’t keep him from graduating.

Now, he’s on his way to becoming Colchester’s newest police officer, where his engaging stories, sense of humor, and friendly demeanor will most definitely give him a leg up in connecting with people.

Family first

“God and family are super-important to me. That’s how we were raised,” says Jake, who is the second oldest of seven. When asked to talk about himself, he, in fact, starts with his siblings.

Amanda is now married and living in Washington, DC, where her husband is studying to be a pastor. His younger sister Cheyenne lives in Montgomery, Vermont, with her husband and little girl, and she works as a dental hygienist. Sister Nikki, “everyone’s personal chef,” is currently in culinary school in Rhode Island. Vanessa is a freshman at UVM, where she’s studying business. His brother Mikey, who is 16, is great at baseball and basketball, “but I like to tease him that I was better because that’s what older brothers do,” says Jake with a laugh. His youngest sister, Jasmine, already a varsity soccer player in 8th grade, “is the sweetest soul you’ll ever meet. We’re all really nice people, but Jasmine is always there for everybody.”

Jake’s mom, who is originally from the Philippines, was a stay-at-home mom when they lived in Alaska, and she home-schooled the kids for several years. She now works at a nursing home. His dad, “an adventurous guy who visited every state in America and wound up in Alaska,” was the reason they ultimately moved back to Vermont in August 2010, to be closer to family.

Daylight and darkness

Jake was 12, and just about to start seventh grade, when the family moved to Vermont. While they were excited to finally live close to the grandparents, aunts, uncles and cousins they had only visited occasionally, the move was also a culture shock.

In Alaska, it’s daylight 24 hours a day in the summer. I remember the sun went down on that first day, and we all said, ‘This is so weird!’ We used to have Little League games at midnight, and it was as bright as noon. And then, our first winter in Vermont, there was sunlight, and we were all like, ‘What is this?’ We were used to it being dark all the time in the winter.

Their dad planted roots in Richford by starting a pick-your-own apple orchard and maple sugaring operation, appropriately named Seven Saplings Farm. Jake recalls helping to plant many of the orchard’s 300 trees, and while he was in high school, he often helped his dad in the sugarwoods. Seeing school buses pull up to the orchard for field trips made Jake feel more a part of what he immediately noticed was a strong community.

“In Alaska, everyone is pretty isolated, and people do their own thing. But in Richford, everyone waves at each other on the roads, and everyone has each other’s backs.”

While Jake now recognizes how lucky he was to grow up in a close-knit Vermont town, he wasn’t sold at first. “For a while, I hated it. I was an Alaskan boy,” he admits. It was also tough having to give up one of his passions—Tae Kwon Do—after the move. In Wasilla, they had a top-caliber mixed martial arts gym just minutes from their house, and Jake never lost a tournament. “But living in Richford, Vermont, there aren’t any big gyms nearby, and when you have six siblings, you have to make sacrifices,” he acknowledges.

Sports, school, and helpful support

In place of sparring, Jake picked up basketball, cross country and baseball, in which he excelled as a pitcher and a shortstop. He was recruited by several colleges for baseball, and he ultimately chose Keene State College—though the baseball program wasn’t the only reason. “I knew I wouldn’t be playing for the Yankees, so academics were always number one,” he says.

When it came to making plans beyond high school, Jake says his parents were always supportive, with his mom encouraging college more than his dad did. “Neither of my parents went to college, and my dad’s thing was, ‘Just find something you’re good at and go with it.’ My mom wanted all of us to go to college, and she actually helped pay for several of her nieces and nephews to attend college in the Philippines,” Jake says.

All of the Cunningham kids benefited from VSAC’s GEAR UP program, which stands for Gaining Early Awareness and Readiness for Undergraduate Programs. VSAC’s GEAR UP provides for counselors to take on a caseload in underserved middle and high schools to help students prepare for higher education and training. Those extra supports were especially helpful for Jake and his siblings since neither of their parents had firsthand experience with applications, scholarships and financial aid.

“VSAC was invaluable to us. Having them on our side made a big difference,” Jake says. “When you’re in high school, you really don’t know anything about financing a college education. Having Liam there to guide us through it made a big impact.”

Longtime GEAR UP counselor Liam Danaher, who now works as an education counselor in New Hampshire, has good memories of Jake and his brothers and sisters.

“In all my years working as a counselor, I remember my time with Jacob fondly. He was a talented student who balanced complex social dynamics, top-level athletics, and high-achieving academics with grace and kindness toward his classmates, teachers, and staff. Jacob was always respectful and kind, something all his siblings shared in common,” says Danaher. “Being able to build meaningful relationships with students and families, like the Cunninghams, is one of the most impactful elements of the GEAR UP program, and one that truly changes lives.”

A time-out, then back in the game

Jake thrived at Keene State, refusing to let injury or illness sideline him for long.

The star baseball recruit was winding up for an impressive college pitching career until an elbow ligament tear during his freshman season ended his time on the field. “That really stunk—but it also opened a lot of other doors to new friendships,” says Jake, characteristically focusing on the positive. “In a way, getting hurt was a blessing in disguise, because I was able to meet a lot more people.”

Then, during Jake’s senior year, he was hit hard with a virus that we didn’t yet understand.

“When Covid hit, I was one of the first people to get it, and I missed six weeks of school. I was throwing up, I was coughing up blood, and I couldn’t get out of bed. I was also working 40 hours a week at the time to cover rent and groceries,” Jake recalls.

I fell so far behind in my classes, and I dropped out for a while. I was very lucky to have a dean at the school who thought a lot of me, and she reached out that spring and asked why I hadn’t graduated. My biggest worry was that I wouldn’t get accepted back at the school. But once I put the time in and wrote the letters, I was able to get back in.

Jake graduated in December 2022. “Getting that diploma was a huge weight off my shoulders.”

The ride(-along) of his life

Jacob Cunningham Officers.jpg

(Photo Caption: Jake Cunningham in the middle, at left his cousin, Sergeant Zac Roy, who invited him on the ride-along, and at right his uncle, Jim Roy, Retired Lieutenant of the Colchester Police Department)

In the spring of 2023, he moved back home and took a summer job with Burlington Public Works. Then, he lived with a friend for a few months in South Boston, where he tried working in sales, but realized that wasn’t his thing.

“I went back home for Christmas last year, and my cousin, who’s a Colchester police officer, asked me if I wanted to do a ride-along. I took him up on it, and I absolutely loved it,” says Jake. “Interacting with people, patrolling different places, and being able to make a positive impact on the community—I loved it all. That day, I met one of the sergeants, and both he and my cousin encouraged me to put in an application.”

Jake started with two weeks of training at the part-time police academy, then moved up to field training, while also working part-time for the department as a uniformed officer. Later this year, he’ll enroll in the full-time police academy, and once he graduates in December, he’ll be out patrolling on his own. “I’ll be the first-ever Colchester police officer to go through that program. So there’s some pressure, but I tend to thrive under pressure,” says Jake. “I’m looking forward to it.”

In fact, Jake’s own journey—which took some unexpected turns—factors into the advice he gives to up-and-coming Vermonters. “Be yourself, but don’t be scared to try new things. You might really enjoy it, and who knows? It might be the gateway to your future."

Soon-to-be Officer Cunningham also offers some more personal advice. “Stay focused. In this day and age, social media puts a lot of focus on other people’s lives. But if you focus on yourself, and if you’re determined and motivated, the sky’s the limit. Also, be nice to people and treat everyone with respect. That goes a long way.”