If nothing else, Bob Sylvester’s legacy as Prep basketball coach was validated when he delivered the school’s long awaited first state championship in 1969. That team, featuring Prep Hall of Famer Jim Fitzsimmons and the late Hal Smith, went 23-1, was ranked No. 1 in New England and came to be regarded as one of Connecticut’s all-time best.
It was Sylvester’s only title, but for 16 seasons at the helm, he was overwhelmingly successful. From 1961-62 until his retirement following the 1976-77 season, the 2006 New England Basketball Hall of Fame inductee compiled a 286-114 record, a 71 percent winning percentage.
From 1966-67 through the title season of 1968-69, Sylvester’s Jesuits went a phenomenal 64-6, winning three MBIAC titles and reaching the state championship game each season.
His teams qualified for the CIAC postseason play in 14 out of 16 seasons, reached the CIAC quarterfinals eight times and the semifinals five times, in addition to his three finals appearances.
Sylvester also coached five of Prep’s 1,000-point scorers: Fitzsimmons, fellow Hall of Fame honoree Jim Lyddy, Sandy Sulzycki, Don Poster and Rob Caseria.