In 1990, Douglas signed a deal with the World Wrestling Federation. His most memorable WWF performance took place at the 1991 Royal Rumble, where he lasted for 26 minutes and 23 seconds. This was the seventh longest time for any wrestler in the Royal Rumble's first four years. Shortly after, he left the company to take care of his ailing father.
In 1995, Douglas returned to the WWF with a college dean character as Dean Douglas. To establish himself, he filmed several vignettes with a chalkboard, "teaching" wrestlers and fans. He would also be shown "taking notes" of his opponents at ringside during some bouts, and frequently carried a paddle (dubbed the "Board of Education") with him to the ring.
He was set to wrestle Shawn Michaels for the Intercontinental Championship at In Your House 4 on October 22, 1995, but Michaels forfeited the title due to injuries incurred after being attacked and beaten by a group of U.S. Marines in Syracuse, New York. However, Douglas immediately had to defend the title against Razor Ramon. Ramon would go on to defeat Douglas, ending his reign at only eleven minutes.
His last appearance on WWF television was at In Your House 5 in December 1995, when he was booked to wrestle Ahmed Johnson. According to the storyline, his back was not in wrestling condition and so he introduced Buddy Landel as his substitute, who was subsequently defeated by Johnson in just forty-two seconds.