Jay Fleischman was a star athlete for the Charles Page High School football, wrestling, and baseball teams from 1985 through 1988. He was named All-State in all three sports and pursued a collegiate football career at Oklahoma State University.

Fleischman outfielded for the baseball team and played in the Oklahoma-California Series.

In wrestling he was the 1988 State Champion at 178 pounds.

In football he was named to the 1980s Oklahoma High School All-Decade Team and went on to play strong safety, free safety, and cornerback for the Cowboys from 1988 through 1992. He lettered in 88, 89, 90, and 92.

He started his first football game as at true freshman in the 1988 Holiday Bowl, playing alongside Barry Sanders and Mike Gundy. The Cowboys defeated Wyoming 62-14.

In the 1989 season he led the Cowboys with four interceptions totaling 15 yards.

In the 1990 season, Fleischman had 73 tackles, including 55 unassisted, and three interceptions totaling 17 yards.

Fleischman currently serves as an assistant coach on the CPHS wrestling and football teams.