In his early years, he was a witness in a federal trial involving illegal activities by a pair of sports agents.
Born in Muncie, Indiana, Douglass graduated from Trotwood-Madison High School in 1982 and then played defensive back for Kentucky.
In September 1985, he suffered from a pinched nerve and was notable for having blown his defensive coverage on two plays in a 27–7 victory over Cincinnati Bearcats.
[7] The last of his interceptions occurred on November 16, 1985, against the Florida Gators when his 43-yard return set up Kentucky's touchdown that gave them a 13–12 lead.
[13] In training camp, Douglas was switched from cornerback to safety and recovered a fumble in the first exhibition game against the Cowboys.
[14][15] He was described by bears scout Rod Graves as "built more like a fullback and could possibly help us inside as a strong-safety type".
"[17] Douglass was one of the final five players cut during training camp by the Bears at the beginning of September,[18] but they re-signed him in late November when they put Jim McMahon on injured reserve.
[21] Chicago Tribune writers noted that Ditka got a kick out of his big earring and fashion sense.
[22] The following season, when Shaun Gayle suffered a season-ending injury for the 1988 Bears, he took over the starting free safety assignment.
[23] In March 1989, he testified against sports agents Norby Walters of New York and Lloyd Bloom of California in United States District Court in Chicago in a trial about "inducing college athletes to sign professional contracts in violation of National Collegiate Athletic Association rules, and of threatening bodily harm".
[43] Later that season, he scored his only career touchdown when he intercepted a Scott Mitchell pass and returned it 32 yards against the Detroit Lions on October 27.
[47] Douglass was in competition with Sam Garnes and Rodney Young for the starting strong safety position for the 1997 NFL season.
[52] He lost the job to Garnes after missing a lot of exhibition time and allowing the latter to see plenty of action.
Upon review by the Ohio High School Athletic Association, he and his staff were found guilty of the charge.