In 1988, Traylor joined the WWF under the name The Big Bossman, based on his previous profession. Bossman made his pay-per-view debut at SummerSlam defeating Koko B. Ware. Bossman made an impact when he attacked Hulk Hogan on Brother Love's interview segment, giving Hogan quite a beating with his nightstick in October 1988 on WWF Superstars of Wrestling. As a villain, he challenged for Hogan's WWF Championship and also teamed with Akeem, the former One Man Gang to form the Twin Towers. The Twin Towers beat The Rockers at WrestleMania V and feuded with Demolition for the Tag Team Championship. On the May 27, 1989 edition of Saturday Night's Main Event, he and Hogan faced each other in a memorable steel cage match for the WWF Title in which 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 joined forces with Hogan at the 1990 Survivor Series along with "Hacksaw" Jim Duggan and Tugboat, defeating Earthquake's team. He also opposed Bobby Heenan's faction The Heenan Family, after Heenan made remarks about Boss Man's mother. Boss Man defeated Heenan's wrestlers such as The Barbarian at the Royal Rumble and Mr. Perfect via disqualification at WrestleMania VII for the Intercontinental Championship. Boss Man then began various, short-lived feuds, first defeating The Mountie in a Jailhouse match at SummerSlam with The Mountie having to spend a night in jail. Another feud was with Nailz in 1992 with Nailz attacking him with a nightstick which kept him out of action for several months; when Bossman returned, he went after his enemy and defeated Nailz in a Nightstick on a Pole match at Survivor Series. He lost his final pay-per-view match to Bam Bam Bigelow at the 1993 Royal Rumble before leaving the WWF in March.
After leaving the WWF in 1993, Traylor had a brief stint in All Japan Pro Wrestling, where he was paired up with Stan Hansen and "Dr. Death" Steve Williams, before returning to the United States to work for World Championship Wrestling. Traylor was originally known as The Boss, but the WWF legal department determined the character to be too similar to the one that Traylor had portrayed in the WWF and forced WCW to change it. As a result, Traylor became the Guardian Angel. He feuded with Big Van Vader for most of 1994. Soon, Traylor turned heel and returned to his original Big Bubba Rogers character. He defeated Sting at Uncensored in March 1995. Big Bubba joined the Dungeon of Doom faction before eventually defecting to the nWo. Eventually, a loophole in Bubba's contract forced him out of the nWo. As a result of this, Bubba became a face once again and began competing under his real name—Ray Traylor and was briefly managed by old nemesis Ted Dibiase, who also recently left the nWo. He frequently worked with the Steiner Brothers during this time period. He began feuding with the nWo, defeating several nWo members such as Scott Hall, Curt Hennig, and Vincent.
Eventually, Traylor returned to the WWF on the October 12, 1998 episode of Raw is War, once again under his Big Bossman persona, but wearing a SWAT-style uniform instead of his old police one. His gimmick was changed from a "cop" into a bully-type personal security officer, or bodyguard-type character, willing to do anything for a price. He was immediately established as a top of the mid-card character, quite a difference from the lower mid-card status he had in WCW just weeks previously. He was introduced as a member of The Corporation, a group of wrestlers controlled by WWF owner Vince McMahon to combat Stone Cold Steve Austin as well as D-Generation X, as The Corporation's "personal security". During his time as a member of The Corporation, Boss Man won the Tag Team Championship with Ken Shamrock and won the Hardcore Championship four times. While still a member of the Corporation, Bossman competed at WrestleMania XV, against Undertaker in a Hell in a Cell match, as 'Taker beat Bossman inside the Cell and "hanged" Bossman in the cage, leaving him suspended about 15 feet in the air.
Most of his matches in the hardcore division were part of his feud with Al Snow. At one point, the storyline involved Al's dog Pepper. At SummerSlam, the pair fought in a match that never made it to the ring; it instead spilled into the backstage area, the street, and finally into a nearby bar. Just prior to the match, Snow was seen setting Pepper's dog carrier near the entrance way. Minutes into the match, Boss Man picked up the carrier, taunted the dog, struck Snow with the carrier, and carelessly tossed it behind him. Announcer Jim Ross apologized immediately for the stunt, and confirmed on air that Pepper had been removed from the box before the match.
Two weeks later, Pepper was taken out of the storyline when he was kayfabe killed by the Boss Man, who then tricked Snow into eating his pet. The storyline concluded with a Kennel from Hell match at Unforgiven. The cage surrounded the ring, with a second roofed cage surrounding the ringside area. The men would start in the ring, with the first man to escape both cages being declared the winner. Between the two cages were a number of attack dogs.
After this, he feuded with The Big Show over the WWF Championship. The feud included a promo where Boss Man showed up at Big Show's father's kayfabe funeral (his father had actually died years earlier) and proceeded to steal Show's father's casket by rigging it to the back of his car and driving off. In a desperate attempt to stop the theft, The Big Show jumped onto the coffin as it was being towed away, riding atop the coffin for a few yards until he lost his grip and tumbled off. Also during the angle, the Bossman uttered the popular, yet often misquoted line, "Ya hear that Paul Wight, you're a nasty bastard and your momma said so!" Months after this feud ended, Big Show wore a t-shirt with the phrase "Big Nasty Bastard" on it. Bossman became the #1 contender for the WWF Championship on the November 15, 1999 edition of Raw. This feud ended with Boss Man being defeated by Big Show at the Armageddon pay-per-view.
Boss Man participated in the 2000 Royal Rumble match. Boss Man eliminated Rikishi (with five other superstars), Chyna, and Faarooq before being eliminated by The Rock. On the March 19 edition of Sunday Night Heat, Boss Man introduced Bull Buchanan as his protégé. They formed a tag team which lasted until the summer when Buchanan left Bossman to seek fame as a solo star. This quest did not last long as he quickly joined the Right to Censor faction. Big Bossman and Bull Buchanan defeated The Godfather and D'Lo Brown at WrestleMania 2000 and beat the Acolytes Protection Agency the following month at Backlash. The team split on the June 5 edition of Raw is War. After they lost to the Hardy Boyz, Buchanan and Boss Man began to argue which led to shoving and eventually Boss Man knocking out Buchanan with his nightstick when Buchanan's back was turned.
In the summer of 2000, Bossman disappeared from mainstream WWF television and wrestled mainly on Jakked and Heat, primarily feuding with Crash Holly. When Traylor returned from an injury in late 2001, he was given a role as the tag team partner of Booker T, as simply The Boss Man. Boss Man served as an enforcer again, only this time for Booker T under the order of Vince McMahon. The team quietly split in late January 2002, and from there on Boss Man wrestled mostly on Jakked and Heat. In April, he formed a short lived tag team with Mr. Perfect after both were drafted to the Raw brand. In May 2002, he competed in his last WWE match, losing to Tommy Dreamer. Traylor was then assigned to train new wrestlers in Ohio Valley Wrestling before being released from WWE in 2003.
Following his departure from WWE, Traylor's last series of matches were in a tournament for the vacant International Wrestling Association of Japan heavyweight title. He made it all the way to the finals before being defeated by old rival Jim Duggan