He returned in March as the manager of Brock Lesnar. Heyman led Lesnar to the WWE Undisputed Championship when Lesnar beat The Rock at SummerSlam. Then at the Survivor Series, Heyman turned on Lesnar and helped Big Show take the title from him. Heyman became the first man in professional wrestling history to manage three successive World Champions when it was revealed that he was Kurt Angle's agent just days after Angle beat Big Show for the title.
Heyman suffered a real life injury in January, when taking the F-5 from Lesnar at the Cow Palace in San Francisco, California. A major falling out between Heyman and McMahon occurred when McMahon ended the Lesnar – Heyman feud on television just weeks before WrestleMania, when Heyman was scheduled to manage Angle in the main event against Lesnar. Heyman took a hiatus a while later.
After McMahon "defeated" daughter Stephanie in October at the No Mercy 2003 pay per view, she was forced to resign from her position as General Manager (GM) of SmackDown!. Heyman returned to television to assume Stephanie McMahon's on-camera role as GM and, unlike the fan favorite character Stephanie portrayed, Heyman's character was portrayed similarly to Eric Bischoff's on Raw- an arrogant dictator of a boss that stacked the odds against his popular wrestlers and favored the unpopular ones. During this time, he re-aligned himself with Lesnar and proceeded to infuriate Undertaker, John Cena, and especially Chris Benoit by making sure he had no WWE Championship opportunities as long as he was GM. Eventually, on SmackDown! right before WrestleMania XX, Heyman asked the entire locker room to back him and Lesnar up against Stone Cold Steve Austin, but they just stood there and walked away from him, including one of Heyman's main supporters, The Big Show.
On March 22, 2004, Heyman appeared on Raw to take part in the annual WWE Draft Lottery. During the show he was drafted to work for Bischoff on Raw, but instead decided to "quit" rather than work for arch-nemesis Bischoff. He was replaced by former client Kurt Angle.
During Heyman's tenure on SmackDown!, he served as the head writer and is credited with being the creative force behind the successful so-called "SmackDown! Six": (Kurt Angle, Chris Benoit, Edge, Rey Mysterio, Eddie Guerrero and Chavo Guerrero). He placed them in a "triple threat tag team feud" (Angle and Benoit, Edge and Mysterio, Los Guerreros) over the WWE Tag Team Championship. This resulted in a string of high-caliber matches over several months, one of which was awarded 2002 Match of the Year by the Wrestling Observer; Heyman was awarded Best Booker. All of the "Smackdown! Six" went on to become world champions, with Edge, Benoit, Mysterio, & Angle becoming World Heavyweight Champions, Eddie Guerrero, Angle, Mysterio and Edge becoming WWE Champions, & Chavo Guererro later becoming ECW World Champion on the later revived ECW.
During 2004, Heyman's on-camera role was again as a manager, this time to the Dudley Boyz (not including Spike Dudley; Heyman's role in that regard disappeared just as Spike became "the boss" of his "big brothers"), and Heidenreich. In these managerial roles, he mainly led his stars in feuds with The Undertaker. Heyman's last appearance on SmackDown! saw him sealed in a coffin by Undertaker during a handicap match which featured Heyman and Heidenreich against The Undertaker on January 6, 2005.
Heyman was heavily involved in the booking and promotion of the June 12, 2005 ECW reunion PPV, One Night Stand. Heyman returned to Raw on May 23 and confronted Eric Bischoff. Among other things, Heyman told him the following: "ECW was a lifestyle, it was anti-establishment, it was counter-culture, and it was up in your face!" Heyman finished it up by setting Bischoff's ECW funeral wreath (made out of barbed wire) on fire. At One Night Stand, a visibly emotional Heyman came to the ring, got on his knees and bowed to the fans, who chanted "Thank you Paul!" He then cut a worked shoot promo insulting Bischoff, Edge, and JBL.
On the May 22 episode of Raw Heyman appeared as ECW Representative promoting One Night Stand. On May 25, 2006 it was announced that ECW would relaunch, as a third WWE brand. Heyman was in charge of the new brand on-camera but had minimal creative input off-camera as well. This would turn Heyman face for the first time in his career. On the May 29 episode of Raw, during a face-off with Mick Foley, Heyman announced that he was granted a draft pick from both Raw and SmackDown! by Vince McMahon. His Raw draft pick was former ECW wrestler (and Money in the Bank contract holder) Rob Van Dam, and his SmackDown! draft pick was Kurt Angle. Angle then came down to the ring and attacked Foley, hitting him with an Angle Slam. Heyman predicted that Van Dam would defeat John Cena at One Night Stand for the WWE Championship and then declare himself the new ECW World Heavyweight Champion. On the June 2 edition of SmackDown!, Heyman served as a guest commentator for Angle's final match on the brand.
At One Night Stand, Van Dam defeated John Cena to win the WWE Championship. After Cena knocked an ECW referee unconscious, Edge (in a disguise) appeared and speared Cena through a table, before taking out SmackDown! referee Nick Patrick, allowing Van Dam to hit the Five-Star Frog Splash on Cena. With no referee available Heyman ran down the aisle to count the pinfall and cement his face turn. The following night on Raw, Heyman confirmed that because the championship match was contested under "ECW rules" (which means, essentially, there are no rules) that the decision stands and RVD is the "Undisputed" WWE Champion. As the WWE Champion, Van Dam was the number one man in the reformed ECW, so on the debut of ECW on Sci Fi the next night Heyman, announced as an "ECW Representative", presented him with the re-instated ECW World Heavyweight Championship. Heyman had previously implied that RVD would "re-christen" the WWE Championship into the ECW Championship. Van Dam, however, elected to keep both title belts and was recognized as both the WWE and ECW Champion.
On the July 4, 2006 edition of ECW, Big Show challenged Van Dam to a match for the ECW Championship. Near the end of the match, Big Show took out the referee prior to RVD hitting a Five-Star Frog Splash on Show. Heyman then came out to count the pin (just like at One Night Stand) but stopped at the count of 2, reverting back to a heel. After realizing what happened, Van Dam began chasing Heyman. The distraction allowed Big Show to recover, and knock Van Dam to the mat. At this time Heyman began barking orders at Big Show. He then instructed Big Show to chokeslam Van Dam on a steel chair that had been used earlier in the match. Big Show pinned Van Dam and Heyman made the 3 count, "screwing" Van Dam out of the ECW Championship. Being that Philadelphia was "the home of ECW", and the audience at the Wachovia Center was the first "true ECW-style" fanbase for an ECW on Sci-Fi show, the fans were so incensed by the title change that many of them threw garbage and debris into the ring. This incident has been referred to by the WWE as the "South Philly Screwjob" (evoking comparisons to the Montreal screwjob).
WWE.com then (kayfabe) announced that Heyman was suspending Van Dam for 30 days (mirroring the legit WWE executive decision, due to his and Sabu's recent arrests on drug possession charges.)
Heyman returned to WWE on the May 7, 2012 episode of Raw as Brock Lesnar's legal advisor. He announced that Brock Lesnar had quit the company, and was "never coming back". The following week on Raw, Heyman confronted Triple H, handing him a lawsuit from Lesnar for "breaching a valid contract", before Triple H would physically grab Heyman by the face and shove him backward into the ropes, leading to Heyman to announce that he will also file a lawsuit against Triple H for "assault and battery". On the June 18 edition of Raw, Heyman declined Triple H's challenge for a match at SummerSlam, on Lesnar's behalf before Triple H punched him . Later that month, Heyman stated that Brock Lesnar will answer Triple H's challenge himself at the 1000th episode of Raw. On the July 23 episode of Raw 1000, Heyman was assaulted by Stephanie McMahon. Lesnar would go on to defeat Triple H at SummerSlam, where, on the following nights episode of Raw, Lesnar once again announced he was leaving the WWE.
On the September 3 episode of Raw, after CM Punk attacked John Cena, Heyman was seen driving the car Punk had entered. This began an alliance between CM Punk and Heyman. Heyman began accompanying Punk to the ring for his matches and promos.
Mr. McMahon cost CM Punk the title at the 2013 Royal Rumble when he restarted the main event match after Punk initially cheated to win and The Rock pinned Punk to become the new champion. On the January 28 edition of Raw, Mr. McMahon aired footage of the attack, which took place two weeks earlier as McMahon pointed out to the audience, in which Heyman paid Brad Maddox and The Shield to help Punk retain his title in his matches, which in turn lead to Maddox receiving a beating from The Shield after Heyman refused to pay him and that The Shield were more useful than Maddox, but Heyman claimed it was somebody impersonating him and he was set up, although he admitted to having lied in his lifetime to save his career during similar crucial moments. Just as it seemed like McMahon would publicly fire Heyman for these actions, Brock Lesnar returned in place of the absent Punk (who was escorted out of the building on McMahon's orders) and he gave the chairman of WWE an F5. The next week on RAW, it was revealed on MizTV that Lesnar was resigned to WWE and Heyman knew nothing about Lesnar's return. During MizTV Lesnar came back and gave an F-5 to The Miz.
On the February 11 episode of WWE Raw, Paul Heyman had his WWE resignation speech halted by CM Punk, and he managed to negotiate a clause with Mr. McMahon that the champion cannot retain the title via count-out of disqualification, as long as The Shield is not involved. Heyman kept good on his promise to support Punk, then unintentionally caused Punk to lose to The Rock at Elimination Chamber (2013) when Punk struck him by mistake.
On the February 25 edition of Raw, Heyman was challenged to a fight by Mr. McMahon, followed by Heyman hitting McMahon with one of his crutches until McMahon turned things around. Brock Lesnar then appeared and was about to attack the chairman until Triple H showed up and went after Lesnar. Later that night, Heyman's client Punk lost to John Cena in a #1 contender match for to decide The Rock's WrestleMania opponent. On the Old School Editon of Raw, Heyman's client,CM Punk, won a Fatal Four-Way match to determine who will face The Undertaker at WrestleMania 29.
On the March 25 episode of Raw, Triple H signed the contract to face Brock Lesnar at WrestleMania, but it was only then when the stipulations were revealed: No Holds Barred, and if Triple H loses, he must retire. On the subsequent episode of Raw, he elaborated that Triple H's managerial career could be on the line. He also dressed up to look like the late Paul Bearer, manager of The Undertaker from his early WWF days, to lure Taker to be attacked by CM Punk on Raw, who was dressed as one of the torch carrying druids. Punk proceeded to empty ash from the symbolic urn onto the dead-man as a sign of disrespect.
Both of Heyman's clients lost to The Undertaker and Triple H in high stakes matches during WrestleMania 29. During Brock Lesnar's match, Heyman received a Sweet Chin Music from Shawn Michaels.
On the April 15 episode of Raw, Heyman informed that his client Brock Lesnar once again challenged Triple H at Extreme Rules in a steel cage match. On the following week, Triple H accepted the match and delivered a pedigree to Heyman. As a response, Lesnar and Heyman invaded the headquarters of WWE and trashed the office of Triple H. In Heyman's words, after years of 'discouraging Lesnar from inflicting more damage and hurt on his opponents or rival', the Pedigree Heyman received was the last straw for him to change his stance and 'encourage' Lesnar to 'hurt Triple H' and to 'maim Triple H' in the Steel Cage, and take him 'to the extreme... and go further and further. In May, WWE's official website began investigating the possibility of Heyman having a third client, either male or female. On the May 20, 2013 episode of Raw, Paul Heyman announced Michael McGillicutty as the newest "Paul Heyman guy" and gave him the new name of Curtis Axel. On the May 27th episode of Raw, Paul Heyman appeared on the Highlight Reel with Chris Jericho, where Jericho challenged CM Punk to a match at Payback which Heyman accepted on Punk's behalf. The next week, Heyman and Jericho signed the contract to make it official. The same week on SmackDown, Jericho faced off against Curtis Axel. As Jericho was closing in on the victory, Heyman stood on the announce table and yelled It's clobbering time, the phrase Punk uses on his way to the ring. Punk's music began to play distracting Jericho long enough for Axel to pick up the victory. Curtis Axel is now currently unbeaten since re-debuting. At WWE Payback, Heyman coached Axel during his match with Wade Barrett and The Miz for the Intercontinental Championship with Axel winning the match and the title. Heyman then accompanied Punk to the ring later in the show for his match with Chris Jericho. After Payback, a WWE.com exclusive video aired with Punk telling Heyman that he is his friend and not his client. CM Punk later turned face on the June 17th edition of Raw, challenging Alberto Del Rio, making sure to mention he doesn't want Heyman managing him anymore. It was also revealed before Punk and Del Rio's match that Punk had advised Heyman not to accompany Curtis Axel to the ring during his match against Sin Cara, but Heyman refused and continued on to accompany Axel to the ring. Following Punk's match, he was attacked by Brock Lesnar. The next week on Raw, Punk demanded answers from Heyman, who swore that he did not ask Brock to attack him. Punk forgave Heyman and hugged him. Punk then faced Darren Young and, following his win, was attacked by Titus O'Neil until Curtis Axel saved him, to Punk's chagrin. Heyman announced that he would team with Axel against The Prime Time Players the next week, again to Punk's disapproval.
At Money In The Bank, Heyman would betray Punk, costing him RAW's Money In The Bank briefcase by hitting him twice using a ladder, knocking Punk off the ladder he was ascending.
On 5 August episode of Raw, Heyman was instructing Axel in Axel's bout with CM Punk, but the match ended in a no contest after CM Punk first choked Heyman, then Brock Lesnar entered the ring and attacked Punk. It ended with Heyman challenging Punk to a 1-on-1 match for next week's episode, which Punk accepted. However, Brock Lesnar decided to spring a trap and made it a one-on-two handicap match. But the plan was foiled when Heyman dared CM Punk to come into the ring and accept the challenge as CM Punk hid under the ring and attacked Lesnar, but failed to attack Heyman as Curtis Axel came to Heyman's aid. At SummerSlam, he stopped CM Punk from getting the win, giving Brock Lesnar an advantage to win, but suffered an arm injury from Punk's Anaconda Vise.
Heyman and Axel delivered a brutal assault to Punk on Raw the following week, with Heyman breaking a kendo stick over Punk's back. Heyman was then set to team with Axel against his "Prodigal Son" Punk in an elimination handicap match at WWE Night of Champions. In an attempt to get out of the match, Heyman pretended to have injured himself after slipping on a spillage backstage. He had a personal doctor act on his behalf, but when the real WWE doctor tried to assess Heyman's supposed injury, Punk ran down to the ring and Heyman ran to safety, enabling Punk to beat up his "doctor" and Curtis Axel. It was revealed as fake there after.
At Night of Champions, Heyman told acting general manager Brad Maddox that he would assault the referee in order to get a quick loss to Punk. Maddox decided to make the match a no disqualification handicap match instead so that such tactics would not apply. Heyman and Axel pleaded with COO Triple H to allow Heyman (a non-athlete) not to compete, but he said the match was still on. Triple H also made Axel defend the Intercontinental Championship against Kofi Kingston in an unexpected bout, but Axel retained the title. Later that night, Punk eliminated Axel from the 2 on 1 match via submission, leaving Heyman alone with Punk. After a beating from Punk and being placed in handcuffs (just as Heyman did to Punk weeks before), Punk was about to destroy Heyman with a kendo stick, when Ryback interfered and cost Punk the match. In subsequent weeks Heyman boasted his win over Punk and Ryback began associating with Heyman. At WWE Battleground Punk would pin Ryback because of a low blow. At Hell in a Cell Punk would go on to defeat both Ryback & Heyman possibly putting an end to their feud. He was heard in a phone conversion on the November 4 edition of Raw and sounded very upset about being injured. On the November 11, 2013 episode of Raw, Heyman stated that he no longer is with Ryback as Ryback never officially accepted his proposal to become a "Paul Heyman Guy." After that, CM Punk would come out to beat Heyman with a kendo stick. On the following Smackdown, Curtis Axel told Ryback that he was no longer a Paul Heyman guy, therefore confirming that he was no longer managed by Heyman. Paul Heyman returned on the December 30th edition of Raw when he was with Brock Lesnar in attacking Mark Henry. He also stood by Lesnar as he feuded with Big Show and The Undertaker in the first four months of 2014. At WrestleMania XXX, he was Lesnar's ringside manager when Lesnar defeated the Undertaker, the man Heyman previously managed early in his career; this was Undertaker's first loss at a WrestleMania, as he previously had a record of 21 WrestleMania wins. On the Raw following WrestleMania, Cesaro revealed himself to be a "Paul Heyman Guy". Cesaro eventually declared himself no longer a "Paul Heyman Guy" on the July 21 edition of Raw. After Triple H announced that Randy Orton would challenge John Cena at Summerslam. Roman Reigns came out and fought with Orton backstage. Heyman then came out and told Triple H to implement "Plan C" which was the return of Brock Lesnar. Lesnar would defeat Cena at SummerSlam 2014 to win the WWE World Heavyweight Championship.
At Royal Rumble, Heyman was at ringside when Lesnar retained his WWE World Heavyweight Championship against Cena and Seth Rollins. At WrestleMania 31 Heyman was at ringside when Brock Lesnar defended his WWE World Heavyweight Championship against Royal Rumble 2015 winner Roman Reigns, Lesnar was unsuccessful as Rollins cashed in his Money in the Bank briefcase and made the match a Triple Threat Match, Rollins pinned Reigns for the win. The next night on Raw, Lesnar was suspended after he demanded a rematch for the title and attacked several innocent people. In July, Heyman and Lesnar returned to the WWE after Lesnar was named the #1 contender to the WWE World Heavyweight Championship. At WWE Battleground, Lesnar defeated Seth Rollins by disqualification, after The Undertaker returned and attacked Lesnar. The Undertaker further explained his actions as revenge not for defeating the streak, but Heyman's constant taunting about it. At SummerSlam, Heyman was at ringside when the match between Brock Lesnar and The Undertaker ended in controversy; the bell was rang as The Undertaker tapped out, but the referee did not see it. This allowed for Undertaker to defeat Lesnar after he passed out to Hell's Gate. At Hell in a Cell, Heyman was also present when Lesnar defeated Undertaker in the rematch, ending their feud.
Heyman returned with Brock Lesnar on the January 11, 2016 Raw, and was ringside with Lesnar for the Royal Rumble. Lesnar was eliminated in the match by Bray Wyatt, after interference by the rest of The Wyatt Family. He also accompanied Lesnar to WrestleMania 32 with Lesnar defeating Ambrose in a No Holds Barred Street Fight. Heyman returned alongside Lesnar on 1 August edition of Raw hyping the Lesnar-Orton match at Summerslam while Lesnar took a RKO from Randy Orton.
On the October 31 edition of Raw, Heyman and Rusev confronted Goldberg. Heyman was speared by Goldberg and later taken by ambulance to a hospital in Hartford, Connecticut.