By Mark Jaffee, Republican-American
Five years have passed since Tim Phipps left the comfort zone at Woodland High he knew for 14 years and the Naugatuck Valley League he knew for more than three decades.
The career change and move to Hopkins School in New Haven, the third-oldest independent prep school in the country, has turned out to be the best of both worlds for the social studies teacher and head football coach.
“I love the camaraderie here and the community at large,” said Phipps of the 714 day students and faculty. “It’s cool the way the school supports each other.”
The 45-year-old teaches seventh-grade geography and advanced placement U.S. History to juniors and seniors.
Phipps had been an assistant coach with the Hawks from the outset of the program in 2001, helping the Hawks to six playoff appearance, and back-to-back Naugatuck Valley League and Class SS state titles in 2004 and 2005.
He was elevated to head coach in the spring of 2014 and guided the team that fall.
But when longtime Hopkins coach Tom Parr stepped down, Phipps knew that it was a challenging job he had to consider because he wouldn’t have to uproot his family — wife Karen, daughters Caitlin, 14, and Maeve, 11, and son Thomas, 9 — which resides in Beacon Falls.
Another selling point was an upgrade to the Hilltoppers’ football field.
“It was redone before I came here,” said Phipps. “It’s a beautiful complex.”
In five seasons, Phipps has guided the Hilltoppers to a 22-21 overall record. In 2018, he led the team to the Metropolitan Independent title and a 5-3 mark last fall.
“We had only four seniors last season, we still have a very young team coming back next fall,” he said.
“We don’t go out and do the traditional recruiting,” Phipps said. “We have a lot of kids coming here from so many different New Haven area towns, different backgrounds and different personalities.”
This past winter, Phipps, an Ansonia native, helped out as a volunteer coach with the Assumption School girls basketball junior varsity team, of which his daughter Maeve is a member. Assumption, coached by Chris and Sarah Ahearn, won the Waterbury Parochial League.
“I was not a good basketball player growing up,” Phipps said. “As a coach, I consider myself a good motivator and a rah, rah type of guy.”
A 1993 Ansonia High graduate, Phipps was a four-year member of the football Chargers, which were Class S state runner-ups in 1991 and 1992. He never earned a varsity start at quarterback.
When he was on the freshmen team in 1989, Phipps gained some starts when Dave Picheco was injured. The Chargers’ varsity QBs back then were Keith Pelatowski (1989) and Rick Lester (1990-91). Picheco was the starter in 1992.
In an unfortunate moment as a freshman, coach John Sponheimer asked Phipps to take a snap and take knee on back-to-back plays to seal a win over Shelton Late in the fourth quarter at Nolan Field. There was one problem, though.
“It was the fumble heard around my world,” noted Phipps. “As the ball hit my hands, I stepped back too soon. The ball popped out and as I dove for the ball, I felt it hit my right hand. But a Shelton player pulled it away from me. I prayed I still had it, but knew I didn’t. Then I heard the referee blow the whistle to clear the pile and one on my teammates picked me up from the ground without the ball in my hands.”
Phipps walked toward the sideline, believing he had blown the game. Shelton would rally to win.
“Assistant coach Steve Pepler tried to be encouraging and Coach Sponheimer tried to be compassionate and stayed composed the best he could,” recalled Phipps. “My dad was a Pop Warner coach and I remember him saying on the way home, ‘You can’t feel sorry for yourself.’”
What did he learn from that moment?
“You can’t hide from your mistakes,” Phipps said. “A mark of true competitor is not necessarily when you hold up your arms above your shoulders when you have won, but rather when you suffer a severe blow and the need to come back the next day. In life you must face setbacks. Football taught me that lesson.”
Phipps never played college football and graduated from the University of Connecticut with a degree in history. He later earned a master’s in education from Sacred Heart University, where he met his wife. The couple will celebrate their 18th anniversary on June 28.
