Benjamin joined WWE's SmackDown brand as a heel on December 26, 2002, forming an alliance with Charlie Haas and Olympic gold-medalist Kurt Angle as their mentor known as "Team Angle". Their first televised match together in WWE was on the January 2, 2003 episode of SmackDown against Edge and Chris Benoit.
They continued their feud with Benoit until No Way Out, when Benoit teamed with Brock Lesnar to defeat Team Angle. The duo won the WWE Tag Team Championship just a month after their debut by defeating the champions, Los Guerreros (Eddie and Chavo Guerrero) on February 6, 2003. The two then went on to compete in their first WrestleMania match at WrestleMania XIX, retaining their tag title in a Triple Threat match against Los Guerreros, and Chris Benoit and Rhyno. Team Angle later lost the title to Eddie Guerrero and his new partner Tajiri at Judgment Day in a ladder match. The storyline concluded on the June 12, 2003 episode of SmackDown!, when Angle confronted Benjamin and Haas and fired them from Team Angle. They then began referring to themselves as "The World's Greatest Tag Team" and won the tag titles back on the July 3 episode of SmackDown. They lost the titles on September 18, after Benjamin suffered a legitimate knee injury during a match against Los Guerreros. Benjamin was sidelined for approximately one month, but the pair competed together again, taking part in a Fatal Four-Way match at WrestleMania XX.
On March 22, 2004, Benjamin was drafted to the Raw brand as part of the 2004 WWE draft. After arriving, Benjamin quickly became a face when he scored an upset victory over Triple H. Benjamin then feuded with Triple H, beating him three times in total: once by pinfall, once by countout and once by disqualification. As part of the storyline, Benjamin then feuded with the other members of Triple H's stable Evolution. Benjamin defeated Ric Flair at Backlash and lost to Randy Orton in an Intercontinental Championship match at Bad Blood.
During a match with Garrison Cade on Heat, Benjamin punched Cade's knee brace, breaking his hand in the process and briefly taking him out of action. Benjamin returned in the fall of 2004 helping Randy Orton fight off Evolution and was later chosen by the fans to compete for the Intercontinental Championship in a match against then-champion Chris Jericho at Taboo Tuesday. Benjamin won the match, giving him his first singles title in the company. During his reign as Intercontinental Champion, Benjamin retained the title against challengers such as Christian at Survivor Series, Maven at New Year's Revolution, and Chris Jericho at Backlash. Benjamin lost the title to Carlito when he debuted on Raw (Carlito used the ropes during the pinfall.) during the June 20, 2005 episode, ending the longest Intercontinental Championship reign of the decade at 244 days.
Benjamin was then depicted as having a "losing streak" over the next several weeks, which led to Benjamin's "Momma" coming to Raw to confront Benjamin. Momma slapped and yelled at Benjamin every time he lost a match. Before long, she assisted Benjamin in his matches, often interfering on his behalf. This led to Benjamin turning heel for the second time in his career. In 2006, Benjamin then began a rivalry with then-Intercontinental Champion Ric Flair. On the February 20 episode of Raw, Benjamin defeated Flair to regain the Intercontinental Championship after Momma faked a heart problem, causing enough of a distraction to allow Benjamin to cheat and win the title. Benjamin continued to feud with Flair, but Momma no longer accompanied him to ringside. Benjamin explained her absence by stating that she was undergoing heart surgery in the hospital.
Benjamin competed in the second Money in the Bank ladder match at WrestleMania 22. Benjamin then began a rivalry with Rob Van Dam, the winner of that MITB match, in an attempt to take Van Dam's Money in the Bank contract. During this time, Benjamin emphasized his new heel persona by now wearing shades, jewelry, and occasional colored shirts while entering the ring. At one point, Benjamin was defeated by his former tag team partner, the returning Charlie Haas, during an episode of Raw. A stipulation added to the match meant that due to this loss, Benjamin had to defend the Intercontinental Title in the same match as his shot at Van Dam's contract, meaning at Backlash it would be a "Winner Takes All" match. Rob Van Dam won at Backlash and became Intercontinental Champion. Benjamin regained the title from Rob Van Dam in a Tornado Tag Team match, pitting Benjamin, Triple H and Chris Masters against Van Dam and WWE Champion John Cena; both the WWE Championship and WWE Intercontinental Championship could be won by whoever pinned the appropriate champion. Benjamin pinned Van Dam, picking up his third Intercontinental Championship. Subsequently, Benjamin feuded with Carlito and others for his Intercontinental Championship before losing the title to Johnny Nitro in a Triple Threat match also involving Carlito at Vengeance.
On the December 4 episode of Raw, Benjamin's former tag team partner Charlie Haas came out to celebrate with Benjamin after he defeated Super Crazy. On the following week's Raw, Benjamin announced The World's Greatest Tag Team was officially back in a segment with Cryme Tyme. They defeated The Highlanders in a match later that same night. They then started a feud with Cryme Tyme, but were largely unsuccessful in defeating them, including a tag team turmoil match at New Year's Revolution on January 7, 2007, where they were eliminated by Cryme Tyme. They finally managed a win over Cryme Tyme, ending their undefeated streak, on the January 29 episode of Raw. Benjamin entered the Royal Rumble match at the namesake pay-per-view, but was eliminated by Shawn Michaels.
On the April 2 episode of Raw, The World's Greatest Tag Team was unsuccessful in defeating the team of Ric Flair and Carlito, but defeated them in a rematch the following week when Haas distracted Carlito, allowing Benjamin to gain the pin over Flair. They won again two weeks later when Carlito turned on Flair, attacking him and allowing The World's Greatest Tag Team to win via countout. They then challenged the Hardy Boyz for the World Tag Team Championship at One Night Stand in a ladder match, but were unsuccessful.
Following this, The World's Greatest Tag Team began a rivalry with Paul London and Brian Kendrick after losing to the duo in their debut match on Raw. A few weeks later, London defeated Benjamin in a singles match, however, on the July 23 episode of Raw, The World's Greatest Tag Team got a tag team win over London and Kendrick to end the rivalry.
Benjamin and Haas then routinely competed against the teams of Hardcore Holly and Cody Rhodes and Super Crazy and Jim Duggan until November, when the team was disbanded due to Benjamin joining the ECW roster.
On the November 20, 2007 airing of ECW, Elijah Burke introduced Benjamin as the newest ECW superstar. Benjamin, who had dyed his hair blond before leaving Raw, began wearing gold wrestling attire and referring to himself as "The Gold Standard". On ECW, Benjamin began once again receiving more airtime and higher profile matches, defeating Tommy Dreamer in his debut. Benjamin then qualified for the Royal Rumble match and won an over the top rope preview. Benjamin appeared in the Rumble match, entering at number 17, but was eliminated by Shawn Michaels. He suffered his first loss since coming to ECW to Kane by count-out, on the January 29, 2008 episode of ECW on Sci Fi. On the February 22 episode of SmackDown!, Benjamin defeated Jimmy Wang Yang in a qualifying match for the Money in the Bank ladder match at WrestleMania XXIV, which was won by CM Punk. After WrestleMania, Benjamin briefly feuded with Punk, before he began an on-screen rivalry with Kofi Kingston, who defeated Benjamin on the April 22 episode of ECW. On ECW's 100th episode, however, Benjamin defeated Kingston, thus ending the latter's undefeated streak. To end the feud, Kingston then defeated Benjamin in an ECW Extreme Rules match.
As part of the 2008 supplemental draft, Benjamin was drafted to the SmackDown! brand. On the July 11, 2008 airing of SmackDown!, Benjamin defeated United States Champion Matt Hardy in a non-title match, earning himself a future title shot. At The Great American Bash, Benjamin once again defeated Hardy to win the United States Championship. Throughout his reign as champion, he retained the title several times against competitors such as R-Truth and Hurricane Helms. On the 500th episode of SmackDown!, on March 20, 2009 Benjamin lost his United States Championship to Montel Vontavious Porter, ending Benjamin's reign at 240 days. Benjamin then participated in the Money in the Bank ladder match at WrestleMania XXV, but failed to win as CM Punk won the match for the second year in a row. On June 29, 2009, Benjamin was traded back to the ECW brand. The following night, Benjamin returned to the brand in a losing effort to the debuting Yoshi Tatsu. He defeated Tatsu in a rematch the following week on ECW. After a tag team match, Benjamin abandoned his partner Zack Ryder during a tag team match, turning Benjamin face. He would soon feud with Ryder and Sheamus over the following weeks. Benjamin and Sheamus began feuding with and traded wins against each other on ECW and Superstars and the feud lasted until Sheamus was moved to the Raw brand on October 26. The next night on ECW, Benjamin lost to Sheamus in Sheamus' final match on the brand.
Benjamin wrestled Christian at TLC: Tables, Ladders & Chairs for the ECW Championship in a Ladder Match, but came up on the losing end. At the Royal Rumble on January 31, 2010, Benjamin entered the namesake match at entry number 20, but was eliminated by John Cena in under a minute. On the final episode of ECW, Benjamin formed an alliance with Vladimir Kozlov. Together, they defeated three members of the ECW roster: Vance Archer, Caylen Croft and Trent Barreta. On the February 26 episode of SmackDown, Benjamin once again qualified for the Money in the Bank ladder match at WrestleMania XXVI, beating CM Punk. However, Benjamin failed to win the match. He defeated the returning Joey Mercury in his last match at the SmackDown tapings on April 20 in a dark match. On April 22, Benjamin was released from his WWE contract.
On the July 26, 2016, episode of SmackDown, a vignette aired promoting Benjamin's WWE return. However, on August 7, Benjamin announced that his return was on hiatus due to a torn rotator cuff, which required surgery. On March 30, 2017, Benjamin announced on Twitter that he was once again medically cleared to compete. However, he also confirmed that he never signed with WWE prior to his injury and was for the time being a free agent.
On August 17, 2017, it was reported that Benjamin had officially re-signed with WWE. On the August 22 episode of SmackDown, Benjamin returned to WWE in a backstage segment, where general manager Daniel Bryan made Benjamin the new tag team partner for Chad Gable. The following week on SmackDown, Benjamin and Gable would defeat The Ascension in their first match as a team. On the September 12 episode of SmackDown, Benjamin and Gable would defeat The Hype Bros and again in a rematch at Hell in a Cell, marking Benjamin's first appearance at a WWE pay-per-view since 2010. On the October 10 episode of SmackDown, Benjamin and Gable would defeat The Hype Bros, The Ascension and Breezango (Fandango and Tyler Breeze) in a fatal four-way match to become the number one contenders for the WWE SmackDown Tag Team Championship. On the November 7 episode of SmackDown, Benjamin and Gable would receive their championship opportunity against The Usos, where they would win the match by countout, however, the Usos would retain the titles. Both Benjamin and Gable quietly turned heel at this point for the first time since 2009. At Clash of Champions, Benjamin and Gable would challenge for the titles again in a fatal four-way tag team match against Rusev and Aiden English, The New Day and The Usos, in which they were unsuccessful. Two days later on SmackDown, Benjamin and Gable beat the Usos in a non-title match, then defeated The New Day and Rusev and English in a triple threat match the following week to earn another shot at the SmackDown Tag Team titles.
On the January 2, 2018 episode of SmackDown Live, Benjamin and Gable defeated the Usos for the SmackDown Tag Team championship but the decision was reversed by the referee when he realized they unknowingly pinned the wrong twin. One week later, when the duo called out the referee and called general manager Daniel Bryan biased, the latter announced they will be getting a rematch at the Royal Rumble pay-per-view in a 2 out of 3 falls match. At the Royal Rumble, Benjamin and Gable lost to the Usos in two consecutive falls. At WrestleMania 34 on April 8, Benjamin competed alongside Gable in the André the Giant Memorial Battle Royal, but neither won. On April 16, Gable would be traded to Raw during the 2018 WWE Superstar Shake-up, thus disbanding the team.
On the April 17 episode of SmackDown, after seemingly wishing Gable good luck on his move to the Raw brand on Twitter, Benjamin would claim his account "got hacked" and began to demoralize Gable, before issuing a challenge to anyone in the locker room. Randy Orton would initially accept the challenge, however, while making his way to the ring, newly drafted United States Champion Jeff Hardy would come out and accept the challenge instead, defeating Benjamin. The following week on SmackDown, Benjamin would issue another open challenge, first answered by Hardy, but Orton would replace him. Benjamin would go onto defeat Orton. Benjamin appeared at the Greatest Royal Rumble in Jeddah, Saudi Arabia, competing in the titular 50-man Royal Rumble match. Benjamin entered the match as entrant number 48 and was eliminated by Chris Jericho. On the May 1 episode of SmackDown, Benjamin teamed with The Miz in a losing effort against Orton and Hardy. Following this, Benjamin would make only make four more televised appearances on SmackDown throughout 2018, losing to Daniel Bryan in June, Jeff Hardy in August and WWE Champion AJ Styles in October. His only win would come over Daniel Bryan on the October 2 episode of SmackDown, after interference from the Miz.
At the Royal Rumble pay-per-view on January 27, 2019, Benjamin competed in the Royal Rumble match, but was eliminated by Braun Strowman. Benjamin returned to television on the March 11 episode of Raw attacking Seth Rollins, and later faced Rollins in a losing effort. In the following months, Benjamin would be mostly off WWE programming, only wrestling in two battle royals: the André the Giant Memorial Battle Royal at WrestleMania 35 in April, and the 51-man battle royal at Super Showdown in June; he would win neither match, however. Benjamin was announced as one of sixteen competitors in the King of the Ring. On the August 27 episode of SmackDown Live, he was defeated by former tag team partner Chad Gable in the tournament's first round. This match would be his first match on WWE television since the match with Rollins in March, and almost a year since his last match on SmackDown. The next week, Benjamin accepted Aleister Black's challenge to fight him, although he was unsuccessful in their match.
As part of the 2019 WWE Draft, Benjamin was drafted to the Raw brand. Benjamin participated in the Royal Rumble match and entered at number ten at the namesake pay-per-view but was eliminated by the WWE Champion Brock Lesnar. On the June 15, 2020 episode of Raw, Benjamin faced Apollo Crews, where Crews won after using the ropes as leverage. Following the match, in a WWE Network exclusive, MVP promised Benjamin a rematch but for the United States Championship, thus teasing an alliance between the two. On the June 22 episode of Raw, Benjamin attacked Crews during the VIP Lounge with MVP before their scheduled match. Despite this, Benjamin was still defeated by Crews. On the July 20 episode of Raw, Benjamin captured the 24/7 Championship after pinning champion R-Truth and officially joined The Hurt Business with MVP and Bobby Lashley. After MVP lost his chance to win Apollo Crews’ United States Championship, Benjamin would lose the 24/7 Championship to Akira Tozawa on the August 3 Raw, in a triple threat match also featuring R-Truth. Later on in the show, The Hurt Business would enter Shane McMahon’s Raw Underground and claim that it’s under new ownership. On the August 10 episode of Raw, Benjamin defeated United States Champion Apollo Crews in a non-title match following a distraction by MVP and Lashley; Benjamin's first victory on Raw in over fourteen years. On the September 7 episode of Raw, Cedric Alexander joined The Hurt Business when he betrayed Crews and Ricochet during a six-man tag team match, attacking them and helping The Hurt Business win the match. On December 20, at TLC, Alexander and Benjamin defeated The New Day (Kofi Kingston and Xavier Woods) to win the WWE Raw Tag Team Championships. Benjamin and Alexander would lose the titles back to The New Day on the March 15, 2021 episode of Raw.
On the March 29 episode of Raw, Lashley lambasted Benjamin and Alexander due to them losing the Raw Tag Team Championships and losing to Drew McIntyre in a 2-on-1 handicap match, effectively barring them from Lashley's WWE Championship match at WrestleMania 37 against McIntyre. This led to Lashley attacking Benjamin and Alexander, kicking them out of the faction in the process. On the May 3 episode of Raw, Alexander tuned on Benjamin after losing to Lucha House Party, turning Benjamin face for the first time since 2018. On the May 10 episode of Raw, Benjamin fought Alexander in a match with Alexander losing to Benjamin. Cedric would however defeat Benjamin on the May 24 Raw.
On the September 27 episode of Raw, Benjamin and Alexander helped Lashley fight off The New Day, in the process reuniting The Hurt Business. Months later in January 2022, after not being seen together, Benjamin and Alexander approached Lashley under the assumption they were still a unit, only to be dismissed. This would cause the pair to launch a sneak attack that evening, but they were easily dealt with. On May 14, 2022, it was reported that Benjamin had suffered an undisclosed injury and would be out of action. He made his return on the June 13 taping of Main Event, in a winning effort against Akira Tozawa. On August 8, Benjamin faced Cedric Alexander during the Main Event tapings in a losing effort, effectively signaling the end of The Hurt Business. Afterwards, they embraced each other and shared a moment in the ring, turning Benjamin face for the first time since 2017.
While continuing his run on Main Event, Benjamin began teaming with R-Truth. On the October 19 edition of Main Event, Benjamin convinced Truth to stop making jokes and start taking himself seriously, believing that they deserved respect. On the November 7 edition of Raw, Benjamin fought Austin Theory in a loss, after Theory challenged him backstage. On the January 9, 2023 episode of Raw, Benjamin and Alexander reunited to take part in a tag team turmoil match. Earlier during the show, Lashley and MVP teased an alliance, with MVP crediting himself for reuniting Benjamin and Alexander, and getting Lashley reinstated on Raw after being suspended. On the February 6 edition of Raw, Benjamin and Alexander defeated Alpha Academy (Chad Gable and Otis) with MVP in their corner, further hinting at a possible reunion; however, nothing would ever come of the potential reunion as it was quietly dropped. Benjamin was released from his WWE contract on September 21.