LAKEVILLE — At the end of February 2025, Dean Diamond led his last game as head coach of the Housatonic ice hockey team.
Diamond’s multi-decade career on the ice was filled with exhilarating wins, tough losses and a lot of pizza.
“My kids joined Salisbury Youth Hockey, so I started coaching Redhawks in ‘96,” said Diamond from his seat in Deano’s Pizza in Lakeville, surrounded by pictures of his teams on the ice and a plethora of trophies.
A pizzeria owner and hockey coach, Diamond’s pies and pucks have long gone hand-in-hand. “The kids would come in here after games and wipe me out of pizza,” he remembered.
Diamond’s own kids advanced from Redhawks to Housatonic co-op hockey in 2003, which is when he began his tenure with the high school team.
For Diamond, hockey was always centered on family. “My three boys all played hockey,” he explained. “My daughter was my hockey manager for four years in high school.” But even after all his kids graduated, he remained coach of both the Redhawks and the Mountaineers.
Diamond coached each team for about 20 years meaning that for a while the two overlapped. Being a coach of two teams and the owner of a restaurant was not easy, “I was living on the ice,” Diamond remarked, “at about 7:30 or 8 [p.m.], after the dinner rush, I would do my hour and a half practice, come back here and finish up.”
Despite his busy schedule, he remained part of the Connecticut Interscholastic Athletic Conference (CIAC) Hockey Committee and sat on the board of the Salisbury Redhawks.
“Every season had memories, every season had great kids and every season meant something,” said Diamond.
Housatonic co-op hockey had good years and bad, winning up to 15 games in a season some years and losing just as many in others. “We had games at Hotchkiss where we would have 200 to 300 people. For many local people, it was Friday night, go to a Housy game at Hotchkiss.”
The best year for the co-op happened to be the one that was cut short by COVID in March of 2020. Diamond recalled, “We were the 15 seed in States, and we beat the number two seed in one of the biggest upsets in Connecticut history. We were all over the news.”
After the huge win, Housatonic was up against an easy team in the quarterfinal and hoped to make it to Yale University’s rink for the semifinals. “We got a call after our biggest win ever that they canceled the rest of the season. Our kids were devastated.”
Co-op disbands
For the team, the biggest challenge was always the roster. Until recently, Housatonic hockey was made up of a five-school co-op consisting of HVRHS, Wamogo High School, Northwestern Regional High School, Oliver Wolcott Technical High School and Torrington High School.
This forced athletes to travel long distances to get to practices and games.
A devastating blow came when Wamogo merged with Litchfield High School in 2024 and the newly formed Lakeview High School chose to join a co-op with Shepaug Valley High School.
“This was extremely unfair,” said Diamond, “The CIAC Co-Op Committee never asked me as a coach how that would affect our numbers.”
This change cost Housatonic three players, including the only two goalies. This — along with some athletes quitting and some injuries — caused the roster to be reduced to as few as seven players in the 2025 season.
After the season, Northwestern and Wolcott Tech backed out, thus ending the Housatonic co-op team.
Next year HVRHS hockey players will join with New Milford High School’s team. Games and practice will be on Canterbury School’s rink, approximately 40 minutes away from HVRHS. Some practices may be held at The Hotchkiss School if possible.
Though he knows his days of coaching are behind him, Diamond remarked, “If there was any way to keep it going, I would do everything in my power to help out.”
