Funny, vibrant, bright, athletic, forever missed
The youngest of three children, Jesse, was welcomed on the first day of Spring by his mother, Michele, his older siblings, Jimmy and Becky, and his father, Jim, who lovingly raised Jesse as his own. Jesse’s arrival completed the Boland family. Becky, who was just 14 when Jesse was born, said; “I pretended he was mine; I would race my mother to his crib to be the first to hold him when he woke.”
Jesse grew up with a strong appreciation for sports, especially football and baseball. He was a loyal New England Patriots and Boston Red Sox fan, often attending Patriots games at Gillette Stadium and Sox games at Fenway, providing endless stats about his teams. He played sports throughout his childhood and high school years, earning the respect of teammates and coaches. Jesse, known as “Boland” or “77,” was a steady teammate, bringing energy and encouragement to everyone around him. He was also the life of the party at pregame pasta dinners at Mama Rancourt’s house. Through the years, Jesse maintained close ties with childhood friends, Steve, Dan, Dylan, and Zack, all of whom were by his side when he passed. Another dear friend, Max, though separated by distance, immediately sent his condolences, love and respect for Jesse.
Jesse enjoyed live music, spending time outdoors, and shared a love of fishing and passion for motocross and dirt bikes with his brother Jimmy, who he attended races with at Unadilla during the summer. Despite being the youngest in the family, Jesse grew to be the tallest, reaching 6’3” by the end of high school. He was sensitive, polite, and kind-a “giant teddy bear.” In his teens, he worked as a hay baler to earn money. He truly loved being able to surprise and give back to others.
After graduating from Massachusetts College of Liberal Arts (MCLA), where he earned a bachelor’s degree in science in sports management, he worked at North Adams Regional Hospital for Berkshire Health Systems and briefly volunteered as a Little League coach. He dreamed of purchasing a remote cabin in the woods and working as a physical therapist.
Those closest to Jesse remember his sharp sense of humor, a natural ability to make people feel welcome, and a love for good food and cooking–a passion he shared with his brother-in-law, J. Jesse was especially gentle with children and adored being an uncle to his nieces and nephew. In his final year, Jesse adopted a boxer mix named Daisy, proudly caring for her and walking her throughout town, stopping in stores for her daily treats. Though he never married or had children, two relationships were deeply meaningful to Jesse, first with his high school sweetheart, Olivia, and later with Michaela. Both women were selfless, positive supporters of Jesse and remain in touch.
Jesse lived with substance use disorder for nine years, a disease that changed him and weighed heavily on both him and his family. Despite periods of recovery, the impact of addiction affected his health, relationships, and sense of self. Ultimately, he was diagnosed with endocarditis and had open heart surgery at age 25. Four years later, Jesse later passed from a brain hemorrhage, a mere month before his brother, Jim.
Jesse is remembered as a loyal friend, a loving son and brother, a devoted uncle, and someone whose quiet acts of kindness left lasting impressions on those around him. He is deeply missed and lovingly remembered.
Jesse’s sister, Becky McConnell, provided the information for this narrative.
March 20, 1994-August 30, 2023-Age 29
Portrait Artist: Clayton Conner
Narrative Writer: Barbara Francois
