Born in Hanson, Massachusetts, Dean Sylvester played three years at Kent State University before the school closed down their hockey program. He ended up finishing his collegiate career at Michigan State.
The San Jose Sharks drafted Sylvester in the now defunct supplemental draft for college late bloomers.
The big-bodied Sylvester turned pro with the ECHL's Mobile Mysticks where he scored 24 goals in 44 games before joining the Kansas City Blades of the IHL. He spent 2 1/2 years in Kansas City including a 33 goal performance in 1997-98. He was a bundle full of energy and a thunderous hitter, which finally caught the attention of a NHL team.
Sylvester signed with the Buffalo Sabres as a free agent on the eve of the 1998-99 season. He played one game for the club in 1998-99 and notched 35 goals for the AHL's Rochster Americans. During the playoffs he led all scorers with 12 goals in 18 games while helping the Amerks reach the Calder Cup final.
In June, 1999, the young forward was traded to the expansion Atlanta Thrashers for future considerations. He scored 16 goals in 52 games for the first year club then split his time between the NHL and the IHL the next season.
Though he impressed with his effort and desire, he retired prematurely in the summer of 2001.