Henry David Oberlander of Norwood, MA passed away on November 5, 2025 at the age of 29 from injuries sustained in an automobile accident. Beloved son of David and Beth Bruno Oberlander of Mansfield, MA, Henry is also survived by his brother Cal Oberlander of Queens, NY, his grandparents Ann Bruno of Mattapoisett, MA and Robert and Anita Oberlander of Rehoboth, MA, as well as many aunts, uncles, and cousins who adored him. He is preceded in death by his grandfather, William “Nonno” Bruno, with whom he shared a special bond. Some in the family suggested that Henry was a Nonno-in-training, largely due to his love of family gatherings, his big hugs, and his effortless smiles.
Born on August 8, 1996, Henry grew up in Mansfield and was an active and adventurous kid. He became obsessed with skateboarding and perfected a number of skateboard tricks. This passion morphed into a love of snowboarding, and Henry enjoyed many Friday evenings with friends at Wachusett Mountain.
Henry was a member of Xaverian Brothers High School Class of 2015. As a freshman, Henry played football and also started wrestling, thinking it would make him better at football. After making the varsity wrestling team as a freshman but only recording one varsity win, Henry dedicated himself to improving his wrestling skills in the off season. He returned sophomore year and recorded forty varsity wins. Henry then went on to be named captain as a junior and senior, to earn accolades including Division 1 South Sectional Champion, and to place at State, All-State, and New England tournaments. While at Xavarian, Henry also played rugby for three seasons.
In addition to sports, Henry loved the community of Xavarian. He was involved in a youth group called Spirit Hawk which was centered on two of his favorite things: conversation and food. He also became a Spirit Hawk Leader and mentored underclassmen. As a junior, Henry was one of six students from his school selected for their leadership qualities and community contributions to attend the annual Xaverian Brothers Sponsored Schools retreat. Perhaps his most significant mentoring was for his brother Cal, both socially and academically.
Henry attended Bridgewater State University and graduated in 2020 with a Bachelor’s degree in psychology. While there, Henry was again named captain of the wrestling team for his junior and senior seasons. He was a two-time NCAA Division III Academic All-American Scholar, and his name is displayed in the BSU wrestling gymnasium to commemorate his successes. After college, Henry became an avid practitioner of Brazilian Jiu Jitsu and represented Connors Martial Arts Academy in Norwood, winning many medals at tournaments. His physical strength was impressive, particularly to his teammates at Connors who also valued his work ethic, humor, and warmth. Henry loved to coach others in the sport he loved. In past years, he coached in a volunteer capacity for the Mansfield High School wrestling team and was also excited to return this winter to Xaverian to volunteer as a coach.
For five years, Henry worked as a laborer in Boston Local 560. This year, he attained a septic inspector license and began pursuing further academic coursework in AutoCAD to enable him to take on a role in his father’s engineering business. Henry had visions of growing the family company.
Henry loved spending time with family and lifelong friends at the beach in Mattapoisett. He loved cooking, baking, and digging into meals that others had prepared; hot wings, charcuterie boards, pho, and steak tips were particular favorites, but he was adventurous and would try anything. Often, Henry would be the one to try the most exotic item on the menu.
Henry was gifted with physical strength, but his soul was kind, gentle, and generous. He took his role as eldest Bruno cousin to heart. According to a young Henry, his brother’s and each successive cousin’s first word was “Henry.” Henry will be sorely missed and never forgotten; this Nonno-in training is leaving a formidable hole in the hearts of his loved ones.
Relatives and friends are cordially invited to attend visiting hours on Friday, November 14, 2025 from 3-7 PM at the Sherman & Jackson Funeral Home, 55 North Main Street, Mansfield. His funeral mass will be celebrated on Saturday, November 15, 2025 at 11 AM in Saint Mary’s Church, 330 Pratt Street (Route 106) Mansfield. Burial will be private and at a later time.
In lieu of flowers, donations may be made to Xaverian Brothers High School in memory of Henry D. Oberlander. www.xbhs.com/gifts-in-memory
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