Big Boss Man debuted in World Championship Wrestling (WCW) as Big Bubba Rogers on the May 31st edition of WorldWide. As Big Bubba, he was a silent bodyguard for Jim Cornette, who, along with the Midnight Express, was feuding with the James Boys (Dusty Rhodes and Magnum T.A., under masks). He got a solid push as a seemingly unstoppable heel and feuded with Rhodes (the top face at the time) in a series of bunkhouse stampede matches in 1986. He and Rhodes were tied for wins in this series, leading to a tiebreaking cage match, which Rhodes won on February 27th. Rogers also defeated Ron Garvin in a Louisville Street Fight at Starrcade 1986.
In the second WarGames match on July 30, 1987, The Road Warriors, Nikita Koloff, Dusty Rhodes, and Paul Ellering defeated The Four Horsemen and Rogers as The War Machine in 19:38 minutes when Road Warrior Animal forced the War Machine to submit by gouging his eyes with a spiked armband.
In June 1988, Rogers joined the WWF as "Big Boss Man", a character inspired by his previous career as a corrections officer. Wrestling as a heel and managed by Slick, Boss Man's post-match routine often included handcuffing his defeated opponents to the ring ropes and beating them with a nightstick or ball and chain.
After defeating Koko B. Ware at the inaugural SummerSlam, Boss Man began his first major WWF angle by attacking Hulk Hogan on "The Brother Love Show". During this feud, he also challenged Randy Savage for the WWF Championship, and formed a team with Akeem to form The Twin Towers. They feuded with Hogan and Savage (who had formed The Mega Powers), and were a key part in the top storyline of Savage turning on Hogan, leading to the WrestleMania V main event; in the later part of a tag match between the four on Saturday Night's Main Event, Hogan abandoned Savage to attend to the hurt Miss Elizabeth and went backstage. After being double-teamed for a while, Savage eventually rallied until Hogan returned to the match. After Savage tagged Hogan in, he slapped Hogan and left him to defeat The Twin Towers on his own. This led to The Mega Powers' demise as Savage beat Hulk in the backstage medical room where fellow wrestlers, managers and staff had to break them up.
At WrestleMania V, The Twin Towers defeated The Rockers (Shawn Michaels and Marty Jannetty) and then, for most of spring and early summer 1989, feuded with Demolition (Ax and Smash) over the WWF Tag Team Championship. Meanwhile, Boss Man concluded his feud with Hogan in a series of steel cage matches; one of the most memorable aired on the May 27 episode of Saturday Night's Main Event, with Hogan's WWF Championship on the line. During the match, Hogan superplexed Boss Man off the top of the cage.
The Big Boss Man turned face on the February 24, 1990 episode of Superstars, when Ted DiBiase had paid Slick to have Boss Man retrieve the Million Dollar Championship belt from Jake Roberts, who had stolen it. 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.
Boss Man then feuded with former partner Akeem, defeating him in less than two minutes at WrestleMania VI. As part of his face turn, he later stopped handcuffing and beating jobbers after matches. He made peace with Hogan, appearing in his corner in his match against Earthquake at Summerslam 1990, and teaming with him at the 1990 Survivor Series, along with "Hacksaw" Jim Duggan and Tugboat, to defeat Earthquake's team.
In the fall of 1990, Boss Man began feuding with Bobby Heenan and The Heenan Family after Heenan continually insulted Boss Man's mother. He won a series of matches against Heenan Family members in 1991, including The Barbarian at the Royal Rumble and Mr. Perfect (via disqualification) at WrestleMania VII in an Intercontinental Championship match, which featured the return of André the Giant. At SummerSlam, he defeated The Mountie in a Jailhouse Match, a match in which the loser must spend a night in jail. This was the only such match ever held by the promotion. Boss Man then briefly feuded with Irwin R. Schyster.
In 1992, Boss Man began feuding with Nailz, an ex-convict character who, in a series of promos aired before his debut, claimed Boss Man had been his abusive officer in prison, and warned he was seeking revenge. On the May 30 episode of WWF Superstars, Nailz — clad in an orange prison jumpsuit — ran into the ring and attacked Boss Man, handcuffing him to the top rope and repeatedly choking and beating him with the nightstick. Boss Man took time off TV to sell his (kayfabe) injuries, eventually returning and having a series of matches with Nailz in the latter half of 1992. The feud culminated at Survivor Series, when Boss Man defeated Nailz in a Nightstick on a Pole match. This was the final push for the Boss Man during this run, as he was subsequently used as enhancement talent against Razor Ramon, Bam Bam Bigelow, and Yokozuna on the house show circuit.
The Big Boss Man's last pay-per-view match of this run came at the 1993 Royal Rumble, where he lost to Bam Bam Bigelow. He left the WWF shortly after a house show in Gatineau, Quebec on March 14. On December 4, he made a one-time return to the WWF as a special guest referee to officiate the main event of a house show in Anaheim, CA between Bret Hart and Jeff Jarrett.
Boss Man returned to World Championship Wrestling (WCW), as "The Boss", on the December 18, 1993 episode of WCW Saturday Night, pinning the International World Champion, Rick Rude, in a non-title match. As a face, he received a title match against Rude at Starrcade '93: 10th Anniversary, but lost. The Boss was then promptly renamed "The Guardian Angel", and wore similar attire to those in the organization he was named after. He feuded with Big Van Vader for most of 1994. In early 1995, he turned heel, and became again known as "Big Bubba Rogers". He defeated Sting at Uncensored in 1995.
In 1996, Rogers joined The Dungeon of Doom. He feuded with former Dungeon of Doom member John Tenta, and newcomer Glacier. By the end of the year, he had turned on the Dungeon of Doom and joined the nWo. His stay in the nWo was brief, with Rogers knocked out by an unknown assailant at the start of the February 17, 1997 edition of Nitro, with Rogers later explaining Eric Bischoff fired him from the nWo while he was temporarily paralyzed. Rogers returned on September 1, now using his real name and vowing to rip Bischoff's head off. He feuded with the nWo, defeating members such as Scott Hall, Curt Hennig, and Vincent. He formed an alliance with The Steiner Brothers, who also sought Ted DiBiase as their manager. The union abruptly ended when Scott Steiner turned on them to join the nWo in February 1998. After losing his final WCW Nitro match to Bill Goldberg on the March 30 episode of Nitro, Rogers won his final match on the following Saturday Night after that he was sent home and WCW let his contract expire.
Rogers rejoined the WWF shortly after his WCW release and once again became "Big Boss Man". On October 12, 1998, he returned to television with a new look, abandoning his blue police shirt for an all-black SWAT-style uniform, including a tactical vest and gloves. He served as Vince McMahon's bodyguard during his feud with Stone Cold Steve Austin and his later feud with D-Generation X. He briefly wore a mask, before his identity was revealed.
Boss Man was one of the first members of McMahon's heel stable, The Corporation, and served as a bodyguard for other members, such as Vince's son Shane. While in The Corporation, Boss Man won the Tag Team Championship with Ken Shamrock, won the Hardcore Championship four times, and lost to The Undertaker at WrestleMania XV in a Hell in a Cell match. After this match, The Undertaker hanged him from the roof of the cage.
In the WWF's Hardcore division, Boss Man's major feud was with Al Snow, a feud that eventually involved Snow's pet chihuahua, Pepper. At SummerSlam, the two had a Falls Count Anywhere match that spilled into the backstage area, the street and, finally, into a nearby bar. Just prior to the match, Snow had set Pepper's pet carrier near the entranceway. Minutes into the match, Boss Man picked it up, taunted Pepper, struck Snow with the carrier and carelessly tossed it behind him.
Two weeks later, Boss Man kidnapped and ransomed Pepper, arranging a meeting in which he fed Snow a meat dish supposedly made from Pepper's remains. The two settled their feud in a Kennel from Hell match at Unforgiven, in which a blue solid steel cage surrounded the ring, itself and ringside surrounded by the chain-link fenced "cell". The object of the match was to escape from the cage and the cell while avoiding "attack dogs" (which turned out to be disappointingly docile) positioned outside the ring. Snow won the match and retained the Hardcore title, which had been returned to him by Davey Boy Smith, who had defeated Boss Man for it. Boss Man would later win back the Hardcore title in a triple threat match involving Al Snow and The Big Show, and would hold it until January 2000, when he lost it to Test.
Boss Man then feuded with The Big Show over the WWF Championship. During the feud, Boss Man showed up at Big Show's father's funeral, made some disrespectful remarks, then chained the casket to the back of his car and drove off. The Big Show attempted to save the coffin by jumping on it, riding it for a few yards before losing his grip and tumbling off, the feud also included a segment in which Boss Man invaded the home of Big Show's mother and forced her on camera to admit her son was born an illegitimate child. Boss Man became the #1 contender for the WWF Championship by defeating The Rock on the November 15, 1999 episode of Raw. At Armageddon, The Big Show defeated him to retain the title and end the feud.
Boss Man entered the 2000 Royal Rumble match, where he eliminated Rikishi (with the help of five other wrestlers), Chyna and Faarooq, before being eliminated by The Rock.
On the March 19 episode of Sunday Night Heat, he introduced Bull Buchanan as his protégé. They teamed to defeat The Godfather and D'Lo Brown at WrestleMania 2000, and the Acolytes Protection Agency the next month at Backlash. On the June 5 Raw is War, after losing to The Hardy Boyz and subsequently arguing, Boss Man knocked Buchanan out with his nightstick when his back was turned and the team split up.
In the summer of 2000, Boss Man disappeared from the WWF's primary television shows, wrestling mainly on Jakked and Heat, where he had a minor feud with Crash Holly until suffering a legit injury in January 2001. When he returned on the December 20, 2001 of SmackDown, he formed a team with Booker T, after Vince McMahon ordered him to be Booker's enforcer. On the December 27 episode of SmackDown, Boss Man and Booker T defeated Stone Cold in a handicap match. On the January 7, 2002 episode of Raw, Boss Man and Booker T were defeated by Stone Cold & The Rock. On the January 17 episode of SmackDown, Boss Man lost to Diamond Dallas Page. At the Royal Rumble, Boss Man competed in the Royal Rumble match where he was eliminated by Rikishi. On the January 24 episode of SmackDown, Boss Man lost to Rikishi. The team quietly split in late January 2002, and Boss Man returned to Jakked/Metal and Heat. On the February 2 episode of Metal, Boss Man defeated The Hurricane. On the February 2 episode of Metal, Boss Man defeated Perry Saturn. In April, he formed a short-lived tag team with Mr. Perfect after both were drafted to the Raw brand. On the March 23 episode of WWF Jakked, Boss Man and Mr. Perfect lost to The APA. On the April 1 episode of Raw, Bossman and Mr. Perfect lost to The Hardy Boyz. On the April 14 episode of Heat, Boss Man lost to Bradshaw. On the April 28 episode of Heat, Boss Man defeated Crash Holly. On the May 6 episode of Heat. Bossman lost to D'Lo Brown. On the May 20, 2002 Heat taping, he lost his final WWE match to Tommy Dreamer. He was released from his WWE contract in 2003.
Big Boss Man passed away on September 22, 2004.
He was posthumously inducted into the WWE Hall of Fame in 2016, with his wife and daughters accepting the award on his behalf.