Cuyler graduated from Southwest High School in Macon, Georgia. He was drafted by the Detroit Tigers in the second round, 46th overall, of the 1986 Major League Baseball draft. Also a standout football player, Cuyler had signed a letter of intent to play college football at Florida State, where he would've joined Deion Sanders as the top incoming defensive backs. He opted to play baseball full time when the Tigers offered a $75,000 signing bonus, although FSU defensive coordinator Mickey Andrews left open the opportunity to return to football.
Cuyler was considered among the Tigers best prospects for four consecutive years by Baseball America, ranking 5th in 1988, 4th in 1989, 5th in 1990, and 3rd in 1991.
1988 Florida State League
Cuyler made his major league debut with the Detroit Tigers on September 6, 1990 at the age of 21 as a defensive replacement in right field for John Shelby. He saw consistent playing time in centerfield and batting ninth to close out the 1990 season, with Lloyd Moseby moving from center to leftfield.

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