After defeating Koko B. Ware at the inaugral SummerSlam, Bossman made his first major WWF impact when he attacked Hulk Hogan on Brother Love's interview segment. During his feud with Hogan, Bossman also challenged for the WWF Championship, held by Randy "Macho Man" Savage; and began teaming with Akeem to form the Twin Towers. As the Twin Towers, Bossman and Akeem feuded mainly with Hogan and Savage (who had formed The Mega Powers alliance), and were strongly involved in the storyline involving Savage's slowly building heel turn and eventual betrayal of Hogan. The Twin Towers were The Mega Powers' opponents the night of Savage's turn; Hogan, who was abandoned by his partner late in the match, rallied to defeat the Twin Towers.
The Twin Towers moved on to defeat The Rockers at WrestleMania V, and feuded for most of the spring and early summer of 1989 with Demolition for the Tag Team Championship. This went on while Bossman was wrapping up his feud with Hogan in a series of steel cage matches; one of the most memorable matches aired on the May 27, 1989 edition of Saturday Night's Main Event, where Hogan superplexed the 350-pound Traylor off the top of the cage.
He later became a fan favorite in early 1990 on The Brother Love Show after refusing to give Ted DiBiase his Million Dollar Championship belt back after DiBiase had paid Slick off for Bossman to retrieve the belt from Jake "The Snake" Roberts' bag that also held Jake's python. Bossman refused to take a payoff and returned the bag with the belt and snake to Jake Roberts. After this change he feuded with former tag team partner Akeem, defeating him in less than two minutes at WrestleMania VI; he also stopped his post-match routine of beating of jobbers during this time. He joined forces with Hogan at the 1990 Survivor Series along with "Hacksaw" Jim Duggan and Tugboat, defeating Earthquake's team.
In 1991, Bossman began feuding with Bobby Heenan and The Heenan Family after Heenan began insulting Bossman's mother. Bossman eventually gained the upper hand against Heenan's wrestlers, getting wins over The Barbarian at the Royal Rumble and Mr. Perfect via disqualification at WrestleMania VII for the Intercontinental Championship; the latter match featured a returning Andre the Giant. Later in 1991, Bossman defeated The Mountie in a Jailhouse match at SummerSlam; the stipulation had it that the loser would (kayfabe) "spend a night in jail."
In 1992, Bossman became involved in a feud with Nailz, whose gimmick was that of an ex-convict; in a series of promos that aired before his debut, Nailz claimed to be abused by Bossman during his incarceration, and warned that he was coming for revenge. During a television taping that aired May 30, Nailz — clad in an orange prison jumpsuit — ran into the ring and attacked the Bossman, handcuffing him to the top rope and repeatedly choking and beating him with the nightstick. Bossman eventually recovered and went after Nailz in a series of matches during the latter half of 1992. The feud culminated when Bossman defeated Nailz in a Nightstick on a Pole match at Survivor Series.
Bossman lost his final pay-per-view match to Bam Bam Bigelow at the 1993 Royal Rumble before leaving the WWF in March.
