The longtime head coach of the Bears did this countless times over the past 21 years, but on Wednesday night it held a special meaning.

Gray won’t be leading the Bears in a head coaching capacity this fall, having retired from the position at the end of the 2022 season.

Gifted with the opportunity to lead the New York team in this summer’s Big 30 All-Star Charities Classic, Gray, who remains a teacher and the athletic director at Frewsburg, jumped at the chance.

A couple of hours after his last practice in Frewsburg ended, Gray reflected on his past couple of decades in charge at his alma mater, while still looking forward to Saturday’s 7 p.m. game at Bradford High School against the best graduated seniors northwestern Pennsylvania has to offer.

Sixteen of his players were named to New York State Sportswriters Association all-state teams during Terry Gray’s 21 years as head coach at Frewsburg. P-J photo by Matt Spielman

“I coached the Big 30 game in 2012, but got sick and was in the hospital when the actual game was played so they asked me back in 2014 to do it again,” he said. ” … We’ve built a relationship with Shawn Llewellyn and have been friends. Last year I was at the game and said ‘I’m retiring, so if you want me to coach again, next year is it.’ I was kind of joking, but I was serious. They called me in January and said ‘We’d love to have you.'”

A pair of Frewsburg players, wide receiver Pat Spencer and quarterback Draven DeJesus, will be playing one final game for Gray on Saturday with the New York squad.

“Pat and Draven have been focal points in our program. They were really strong leaders and made the transition from 11-man to 8-man back to 11-man their senior year,” Gray said. “When you go through struggles, it strengthens those bonds. They’ve become really good football players and they fit right in with these other all-stars.”

The final few years of Gray’s tenure at Frewsburg have been the most frustrating, but also some of the most rewarding.

A decline in enrollment at the school forced Frewsburg into a merger of the football program with Randolph for a couple of years before going back and forth from 8-man football to 11-man football.

“Multiple schools have merged and some don’t have a team anymore. I think what’s held us together is the extra stuff we’re teaching,” Gray said. “No matter the number, you have the same philosophy. We’ve used the game of football to teach about the game of life. … We’ve always tried to support these kids and have them become better men, dads, community members and husbands.”

Frewsburg’s most successful season under Gray came in 2013 when the Bears won the Section VI Class DD championship with a 33-0 win over Cattaraugus-Little Valley at then-Ralph Wilson Stadium. The Timberwolves had beaten Frewsburg 21-7 just three weeks earlier.

“When I was young in my career, Bob Krenzer was at Pine Valley, Tim Bergen was at Ellicottville, Pat Slater was at Randolph and Howard McMullin was at Clymer. I was the young guy,” said Gray, who was an assistant coach for two years under Slater at Randolph and three years under Chris Krantz at Southwestern before taking over as head coach at Frewsburg in 2002. “It was fun taking your lumps, staying humble and then finally coming into your own and winning those games.”

Over the years, Gray has seen 16 of his players named to New York State Sportswriters Association Class D all-state teams. Named to the first team were Steve Coan (2004, offensive line), Dalton Peterson (2011, wide receiver), Thad Johnson (2011, all-purpose), Cordell O’Brien (2015, wide receiver), Cole Gregory (2016, offensive line) and Zach Winters (2021, quarterback/running back).

“In 2011, we beat Randolph (to end the Cardinals’ season) to go to the sectional final and lost to Maple Grove by a touchdown at the stadium,” Gray said. “That really sticks out.”

Recognized on second teams were John Rachuna (2005, kicker), Corey Raymond (2009, wide receiver), Clark Gregory (2010, offensive line), Robbie Stearns (2011, punter), Nick Mitchell (2011, linebacker), Zach Haller (2014, defensive line), Brady Collver (2015, running back) and O’Brien (2016, wide receiver).

“I can remember the climb, 2-6 our first year with two overtime losses, then 4-4,” Gray said. “I remember beating Bergen and Ellicottville in a playoff game at home. We beat Krenzer at Pine Valley in his last game. Those are little milestones that make you know you are doing something right.”

Honorable-mention selections included Terry’s son, Trent (2016, quarterback), Caleb Caldwell (2016, honorable mention) and Joel McLaughlin (2021, lineman).

“The first time Trent starts at quarterback, the first time Traden (Gray’s youngest son) started at quarterback … Traden overcoming his arm injury and coming back his senior year; I remember all of those things,” Gray said. “When I left Southwestern and came to Frewsburg, my kids were little and I said if I’m going to be a head coach … the only way I was going to do it was if they were right there with me.”

Trent, Traden and Dani, Terry’s middle daughter, were all part of the program through the years. Traden will play basketball at Clarion University this fall while Dani will graduate with a medical degree.

Trent, on the other hand, is now a social studies teacher at Frewsburg and one of the coaches that will carry on his father’s program. Rob Collver, a longtime assistant with Terry, will be the head coach.

“(Stepping down) was the ultimate decision. I had contemplated it for a couple of years. … It was hard. … I have coached or played football since I was in 10th grade,” Terry said. “Knowing that we have Coach Collver and Trent, they are going to do a great job.

“I couldn’t have left it to nothing,” Gray added. “I felt the program is in great hands.”