Kirk Benson grew up in the small upstate New York town of Bainbridge. Born to Doctors Kenneth and Jane Benson, he was the sixth of eight children. He began wrestling in elementary school gym class in fifth and sixth grade. The following year, he joined the junior high school team and competed at 76 pounds in seventh grade and 86 pounds in eighth grade. He often reflects on his junior high years as the time when he was first introduced to the concepts of sportsmanship and the importance of winning and losing with humility, honor, and pride.

As a freshman in high school, Kirk joined the Bainbridge-Guilford Bobcats wrestling squad and competed all four years. His coach, Vern Wallace, taught him how to wrestle, how to win humbly, how to demonstrate good sportsmanship, and how to lose gracefully. Vern was a tremendous source of inspiration to Kirk. He distinctly remembers one match in which he failed to make weight and, as a penalty, had to wrestle up a weight class. He was quickly put on his back and suffered his first career loss by pin. Though he felt his shoulders never touched the mat, believed the referee was terrible, and blamed his coach, it became another important lesson in humility, accepting loss, and being a true team player.

Kirk went on to wrestle at Muskingum College in Ohio, a small Division III school. As a sophomore, he won the Ohio Athletic Conference and finished seventh overall at the Division III National Tournament, earning All-American status.

After graduating in 1983, he coached the Stewart Junior High wrestling program in Oxford, Ohio. The following year, after getting married, he moved to Gloucester, Massachusetts. While living in Gloucester, he came across an advertisement seeking a wrestling coach for the Landmark School in Beverly, Massachusetts. He coached there for one season in 1988, but work conflicts prevented him from returning for a second season.

In 1991, he attended the league championship match between Lynnfield and Hamilton-Wenham. He no longer remembers who won, but the experience sparked the idea of becoming an official and re-entering the wrestling world. He approached the match official—an older man with athletic tape across the bridge of his glasses—who shook his hand so firmly he thought it might break. This was his first meeting with the legendary George Bossi, marking the beginning of a long friendship with one of wrestling’s great coaches and personalities. Thanks to George, Kirk went on to officiate for the next 25 years. In 2003, he was honored with the Massachusetts Interscholastic Wrestling Coaches Association Referee of the Year Award, and in 2009 he received the Massachusetts Interscholastic Wrestling Coaches Association Outstanding Wrestling Official Award.

Over the years, many colleagues questioned why Gloucester did not have a wrestling program, especially given the city's reputation as a tough, hardworking community with a long history of strong athletic teams. Determined to establish a new tradition, Kirk set out to bring wrestling to Gloucester. In 2007, with the help of Steve McCarthy, a former Winchester High School wrestler, and Josh Ulrich, a former Marblehead wrestler, he launched a youth wrestling program on Cape Ann.

After several years working with the youth program, Kirk inquired about creating a varsity-level team at Gloucester High School, and the idea was met with great enthusiasm. In 2012, with the support of Head Coach Matt Swanson, a standout Connecticut wrestler, a varsity program was officially established. Growth was gradual, but with dedicated youth wrestlers advancing through the program—and continued support from families, the community, and the Gloucester Public School system—the program has flourished.

Today, the Gloucester wrestling program proudly includes two All-State champions, four state champions (including one two-time champion), nine sectional champions, six 100-match winners, one girls’ state champion and two-time All-State finalist, and one four-time girls’ youth New England champion. The program looks forward to providing many more young wrestlers with inspiring and memorable experiences.

In 2015, Kirk was honored by the Massachusetts Chapter of the National Wrestling Hall of Fame as the Massachusetts Up-and-Coming Wrestling Coach of the Year. He remains committed to giving back to the sport of wrestling and hopes to never lose sight of the fact that it is, above all, for the youth and their future. Kirk believes that the wrestling community fosters a powerful bond among individuals who understand what it takes to succeed.