In late 1988, Slick began managing Akeem and Big Boss Man in the World Wrestling Federation. Slick then paired the two together and billed them as The Twin Towers. The Towers would make their pay-per-view debut on November 24, 1988 at the 1988 Survivor Series, captaining a team with Haku, Ted DiBiase, and The Red Rooster against a team captained by The Mega Powers (Hulk Hogan and Randy Savage), Hercules, Koko B. Ware and Hillbilly Jim in a five-on-five elimination match. The Towers' team lost and Hogan and Savage were the survivors of the match, but not before both received beat-downs from The Towers.
While still teaming as the Towers, Boss Man and Akeem would have many single matches against Hogan and Savage. Then, on the January 9, 1989 episode of WWF Superstars of Wrestling, WWF World Heavyweight Champion Savage had a match against Akeem. When Savage delivered his diving elbow drop to Akeem and went to pin him, Boss Man then came and entered the ring and attacked Savage with his nightstick, and Akeem was disqualified. Hogan then ran down and attacked the Towers who then left the ring. On January 7, 1989, when Hogan faced Akeem on Saturday Night's Main Event XIX, Boss Man again interfered in the match, and then Miss Elizabeth, who was the manager of the Mega Powers, came to help Hogan, who was then followed by Savage, who then cleared the ring of the Towers.
Also during January 1989, the Towers would achieve success, when they would score several wins over The Young Stallions (Paul Roma and Jim Powers). Weeks later on February 3, 1989, on The Main Event II, the Towers had a match against the Mega Powers, who were having dissension between them. During the match, Akeem threw Savage out of the ring, causing him to land on top of Savage's manager Elizabeth, knocking her unconscious. When Hogan saw what happened, he left the match and carried Elizabeth from the ring to the medical area. When he returned to the ring, he wanted to tag Savage, but Savage, who was furious with being abandoned during the match and very angry that he had to face the Towers alone, then slapped Hogan in the face, and then left Hogan the face the Towers by himself. Hogan then defeated the Towers by himself and the Mega Powers won the match.
Two months later at WrestleMania V, the Towers defeated The Rockers (Shawn Michaels and Marty Jannetty) after Akeem pinned Michaels following a powerbomb by the Boss Man and Akeem's own Air Africa finisher. Though the Towers were still wrestling as a team, Boss Man pursued the WWF World Championship and wrestled a major singles match, when he received a title shot against the new WWF Champion Hulk Hogan after Hogan regained the WWF World Title from Savage at WrestleMania V, after the Mega Powers disbanded.
On Saturday Night's Main Event XXI, Boss Man faced Hogan in a steel cage match, and during the match Hogan superplexed Boss Man of the top of the cage; Boss Man ended up losing the match. Shortly afterwards, The Towers began a feud with the WWF Tag Team Champions Demolition (Ax and Smash) as they pursued the tag team titles. The Towers would lose every house show match they had against Demolition, some by pinfall, and some by disqualification. Even after Demolition lost the tag titles to The Brain Busters (Arn Anderson and Tully Blanchard), The Towers continued to feud with Demolition. The Towers teamed with André the Giant against Demolition and King Duggan at SummerSlam 1989, much to surprise of commentator Jesse Ventura, Demolition and Duggan won the match.
At the 1989 Survivor Series, The Towers were to team with The Honky Tonk Man and Rick Martel as a team called The Enforcers against a team called the Dream Team, consisting of Dusty Rhodes, Brutus Beefcake, Tito Santana, and the Red Rooster, but the Boss Man's partner Akeem but was replaced at the last moment by Bad News Brown. The Enforcers lost the match, with the Boss Man the last one to be pinned by Rhodes.
During this time, the Boss Man was actually embroiled in a feud with Dusty Rhodes after Rhodes had stolen The Boss Man's nightstick and handcuffs.
Following the conclusion of his feud with Rhodes early 1990, The Boss Man became a face when "The Million Dollar Man" Ted DiBiase paid Slick to have the Boss Man retrieve the Million Dollar Championship belt from Jake "The Snake" Roberts, who had stolen it. On a February 24, 1990 episode of WWF Superstars of Wrestling, The Boss Man retrieved a bag containing both the belt and Roberts' pet python, Damien. On The Brother Love Show, he refused to accept DiBiase's money for the bag, and returned it to Roberts. After that, the Towers disbanded.