Swagger lost a Raw dark match on August 18, 2008, to William Regal.
On September 9, 2008, Swagger made his WWE debut on the ECW brand, winning a match against a local competitor. He immediately established himself as a heel by starting a feud with Tommy Dreamer. He attacked Dreamer on the September 23 episode of ECW when Dreamer attempted to stop Swagger from attacking Chase Stevens. He later defeated Dreamer in a normal match and an "amateur wrestling challenge" competition. After weeks of feuding, their rivalry ended in November in an Extreme Rules match, which Swagger won.
He then sought to challenge Matt Hardy for the ECW Championship and was named the number one contender on the December 30 episode of ECW. On the January 13, 2009 episode of ECW, Swagger defeated Hardy to win his first title in WWE, the ECW Championship. His undefeated streak in singles competition ended on the February 3 episode of ECW when he lost to Finlay in a non-title match. After successfully defending his title against Hardy at the Royal Rumble and Finlay at No Way Out, Swagger began a feud with the returning Christian, who he lost the ECW Championship at Backlash, ending his reign at 104 days. He attempted to regain the title against Christian at Judgment Day and in a triple threat hardcore match at Extreme Rules also involving Dreamer but was unsuccessful in both attempts. His attempt to win the ECW Championship at The Bash in an ECW Championship Scramble also failed.
On June 29, 2009, Swagger was traded to the Raw brand, making his debut as part of a three-on-one gauntlet match against WWE Champion Randy Orton, in which he got himself purposely counted out in order to make an impression on Orton. On the July 13 episode of Raw, he won his first match on the brand by defeating Montel Vontavious Porter (MVP). He then feuded with MVP for several weeks, culminating at SummerSlam, in a match that MVP won. After his short feud with MVP ended, Swagger began pursuing the United States Championship. He had a title match on September 21 against Kofi Kingston, but lost the match by countout after stealing the championship belt and leaving the arena with it, but Kingston later took it back while Swagger was in a physical confrontation with The Miz. Swagger made another unsuccessful attempt at the title at Hell in a Cell in a triple threat match against Kingston and The Miz. At the Royal Rumble, Swagger entered at number 26 in the Royal Rumble match, but was later eliminated by Kofi Kingston.
On the March 1, 2010, episode of Raw, Swagger defeated Santino Marella to qualify for the Money in the Bank ladder match at WrestleMania XXVI, where he won, earning a contract for any WWE world championship over the following year. On the first episode of Raw following WrestleMania, Swagger tried to cash in his Money in the Bank contract against the WWE Champion John Cena, but changed his mind when he realized that Cena was not incapacitated enough to be defeated easily. As the match had never started, Swagger retained the contract for use at a future date.
Swagger cashed in the contract during the SmackDown taping on March 30, 2010, after then-World Heavyweight Champion Chris Jericho had been speared by Edge. Swagger went on to defeat Jericho to win the World Heavyweight Championship for the first time. Following his championship win, Swagger began to develop a more serious persona: previously he had been known for doing push-ups and beating his chest during his ring entrance. He successfully defended the title against Edge and Jericho in a triple threat match on the April 16 episode of SmackDown and against Randy Orton in an Extreme Rules match at Extreme Rules. At Over the Limit, Swagger retained the title against The Big Show by intentionally disqualifying himself. At Fatal 4-Way, Swagger lost the championship to Rey Mysterio in a fatal four-way match also involving CM Punk and The Big Show. Following the Fatal 4-Way pay-per-view, Swagger began attacking Mysterio in the lead up to his rematch at the Money in the Bank pay-per-view in July, however he failed to regain the championship.
In late 2010, Swagger began being accompanied to the ring by his mascot, the Swagger Soaring Eagle, who was portrayed by Chavo Guerrero. At TLC: Tables, Ladders and Chairs, Swagger competed in a triple threat ladder match for the Intercontinental Championship against Kofi Kingston and champion Dolph Ziggler, in which Ziggler retained.
On the February 28, 2011 episode of Raw, Swagger was announced as Michael Cole's trainer for his match at WrestleMania XXVII against Jerry Lawler. On the March 28 episode of Raw, Swagger faced Lawler in a singles match, which he won by disqualification after Lawler attacked him with a steel chair. At WrestleMania, Swagger receive a Stone Cold Stunner from the guest referee, Stone Cold Steve Austin, when attempting to withdraw Cole from the match. Cole went on to win the match via disqualification. On April 26, Swagger was drafted to the Raw brand as part of the 2011 supplemental draft. At Extreme Rules, Swagger teamed with Cole to defeat Jerry Lawler and Jim Ross in a Country Whipping match. Swagger ended his partnership with Cole on the May 16 episode of Raw, after Cole insulted him.
Beginning on May 23, Swagger feuded with Evan Bourne, with both men trading victories on several episodes of Raw. At Capitol Punishment, Bourne defeated Swagger to end the feud. Swagger competed in his second Money in the Bank ladder match at the Money in the Bank pay-per-view, however he was unsuccessful as the match was won by Alberto Del Rio.
On the August 15 episode of Raw, after defeating Alex Riley, Swagger suggested to Vickie Guerrero that she should manage multiple clients, in the vein of managers like Bobby Heenan and Freddie Blassie. The following week, Swagger had a "tryout" match, but was distracted by Guerrero arguing with Dolph Ziggler at ringside, and lost the match. Swagger and Ziggler continued to fight over Guerrero for the next few weeks, which led to a match being for Ziggler's United States Championship at Night of Champions, also involving Riley and John Morrison. At the pay-per-view, Swagger was unsuccessful in winning the title as Ziggler retained. On the September 19 episode of Raw, Guerrero agreed to manage Swagger. As a result, Swagger and Ziggler formed an alliance, with Swagger helping Ziggler retain his championship. At both the Hell in a Cell and Vengeance pay-per-views, Swagger and Ziggler unsuccessfully challenged Air Boom (Evan Bourne and Kofi Kingston) for the WWE Tag Team Championship.
On the January 16, 2012, episode of Raw, Swagger won the United States Championship for the first time by defeating Zack Ryder. At Elimination Chamber, Swagger successfully defended his title against Justin Gabriel. On the February 27 episode of Raw, Swagger and Ziggler unsuccessfully challenged Primo & Epico for the WWE Tag Team Championship in a triple threat tag team match, also involving Kofi Kingston and R-Truth. On the March 5 episode of Raw, Swagger lost the United States Championship to Santino Marella, ending his reign at 49 days. On the following episode of SmackDown, Swagger failed to regain the United States Championship in a steel cage match, after Marella escaped through the cage door. On the March 19 episode of Raw, Swagger was announced as a member of Team Johnny at WrestleMania XXVIII. On the April 2 episode of Raw, Swagger and Ziggler unsuccessfully challenged Marella for the United States Championship in a triple threat match. In May, Swagger and Ziggler unsuccessfully challenged Kofi Kingston and R-Truth for WWE Tag Team Championship, first at Over the Limit and second on the May 28 episode of Raw. On the June 11 episode of Raw, Swagger and Ziggler competed in a fatal four-way elimination match for a number one contenders spot to the World Heavyweight Championship; however, he was eliminated after Ziggler pinned him. The following week, Guerrero, finally tired of the bickering between Swagger and Ziggler, arranged for a match between them; Ziggler won the match, thus ending their partnership.
On the June 25 episode of Raw, Swagger once again unsuccessfully challenged Santino Marella for the United States Championship. Following this loss, Swagger went on a three-month losing streak against the likes of Tyson Kidd, Sheamus, Brodus Clay, and Ryback. After again losing to Sheamus on the September 3 episode of Raw, Swagger told Raw General Manager AJ Lee he would take "time off".
On the February 1, 2013 episode of SmackDown, Swagger returned, and demanded that SmackDown General Manager Booker T put him in the Elimination Chamber match at Elimination Chamber. Later on that night, Swagger made his in-ring return by defeating Kofi Kingston. On the February 11 episode of Raw, Swagger debuted a new manager, Zeb Colter, a self-proclaimed great American hero who strongly advocated anti-immigration beliefs; Swagger's character was influenced by Colter to display similar traits. That same episode, Swagger defeated Zack Ryder to qualify for the Elimination Chamber match that would determine the number one contender for the World Heavyweight Championship which he also won after last eliminating Randy Orton. On the March 18 episode of Raw, Swagger broke the ankle of Alberto Del Rio's ring announcer Ricardo Rodriguez after Rodriguez tried to save Del Rio from Swagger's vicious assault.
On April 7 at WrestleMania 29, Swagger unsuccessfully challenged Del Rio for the World Heavyweight Championship. The following night on Raw, Swagger and Zeb Colter were defeated by Del Rio in a two-on-one handicap match after forcing Swagger to submit to the Cross Armbreaker. Immediately following, Dolph Ziggler cashed in his Money in the Bank briefcase on Del Rio to become the new World Heavyweight Champion. Swagger would then feud with both Del Rio and Ziggler over the World Heavyweight Championship, with Swagger defeating Ziggler in a non-title match the following week and Del Rio attacking him afterwards. Swagger was originally booked to face Ziggler and Del Rio in three-way ladder match for the World Heavyweight Championship at Extreme Rules, however, Ziggler would suffer a legitimate concussion at a SmackDown taping due to a kick from Swagger, thus removing their match from the card. As a result of Ziggler's injury, Swagger instead would be booked to face Del Rio in a number one contender "I Quit" match at the pay-per-view on May 19, which Del Rio won. In June, Swagger took a leave absence to undergo surgery on his hand, which sidelined him for the remainder of the month.
Swagger returned on the July 1 episode of Raw, accompanying Zeb Colter's new client Antonio Cesaro to his match with Cody Rhodes. At the Money in the Bank pay-per-view, Swagger and Cesaro competed in the World Heavyweight Championship Money in the Bank ladder match, but were both unsuccessful as the match was won by Damien Sandow. The following night on Raw, Swagger and Cesaro, now billed as The Real Americans, teamed together for the first time, but ended up being defeated by The Usos. During the Night of Champions pre-show, the Real Americans competed in a number one contender Tag Team Turmoil match for the WWE Tag Team Championship, in which they were the last team eliminated by The Prime Time Players (Darren Young and Titus O'Neil). Simultaneously, the Real Americans began a feud with the returning Santino Marella after he defeated both of them in singles competition. On October 6 at Battleground, the Real Americans defeated Marella and The Great Khali in a tag team match. The Real Americans moved onto feuding with Los Matadores, culminating in a tag team match on October 27 at Hell in a Cell, which Los Matadores won. The following night on Raw, The Real Americans defeated WWE Tag Team Champions Cody Rhodes and Goldust in a non-title match. At Survivor Series, Swagger teamed with Cesaro, Roman Reigns, Dean Ambrose and Seth Rollins in a 5-on-5 traditional Survivor Series tag team match, in which their team was victorious over Rey Mysterio, Cody Rhodes, Goldust and The Usos' team. At TLC, they also challenged for the WWE Tag Team Championship again in a losing effort in a fatal four-way match also involving RybAxel and the team of Big Show and Rey Mysterio. Swagger would enter the 2014 Royal Rumble match at entrant number seven, but was eliminated by Kevin Nash. On the February 14 episode of SmackDown, Swagger became the number one contender for the Intercontinental Championship after winning a fatal four-way match, defeating Kofi Kingston, Rey Mysterio and Mark Henry. However, Swagger would advance to Elimination Chamber, where he would face the current Intercontinental Champion, Big E, and would lose the match.
During the pre-show of WrestleMania XXX, the Real Americans were the final team eliminated during a fatal-four-way match for the WWE Tag Team Championship. Swagger blamed Cesaro for the loss and put Cesaro in the Patriot Lock before Colter demanded that the duo shake hands. Cesaro instead retaliated with a Cesaro Swing on Swagger. Later during the pay-per-view, Cesaro was a surprise entrant in the André the Giant Memorial Battle Royal, which he won by last eliminating Big Show by body slamming him out of the ring, which mirrored Hulk Hogan's momentous body slam of André. Swagger retaliated by attacking Cesaro on the following Raw and then destroying the trophy, thus ending the stable.
Following the dissolution of their team, Swagger would feud with Cesaro, with Rob Van Dam also being drawn into the feud, with the three competing in a triple threat elimination match at Extreme Rules, which Cesaro won. On the May 5 episode of Raw, Swagger and Zeb Colter would begin to rant about the foreign superstars in WWE, before being interrupted by the debuting Adam Rose. Over the next month, Swagger would lose matches due to Rose causing a distraction by appearing at ringside with his "Rosebuds". This would lead to a match on the June 2 episode of Raw, where Swagger would be defeated by Rose. At the Money in the Bank pay-per-view, Swagger would compete in the Money in the Bank ladder match, which was won by Seth Rollins.
On the June 30 episode of Raw, Swagger turned face for the first time in WWE, after he and Colter would confront Rusev and Lana about them disrespecting America. This would lead to a number of matches between the two, with Swagger being defeated by Rusev at both Battleground and SummerSlam. On the December 1 episode of Raw, Swagger would find Colter assaulted backstage, with Rusev later admitting to the attack. At TLC: Tables, Ladders and Chairs, Swagger would challenge Rusev for the United States Championship, in a losing effort, thus ending their feud.
Around this time, Swagger appeared on television less frequently. At the Royal Rumble, Swagger competed in the 2015 Royal Rumble match, lasting a while before he was eliminated by Big Show. At WrestleMania 31, Swagger participated in the second annual André the Giant Memorial Battle Royal, in which he was again eliminated by Big Show. Swagger made a rare Raw appearance on November 2, encountering his former manager Zeb Colter, only to be interrupted by Alberto Del Rio, Colter's new client. This started a feud between the two, which culminated at TLC: Tables, Ladders and Chairs with Swagger challenging Del Rio for the WWE United States Championship in a chairs match, which Del Rio won. At the 2015 Tribute to the Troops event, Swagger defeated Rusev by submission in a "Boot Camp" match.
On January 24, 2016, at Royal Rumble, during the kick-off show, Swagger teamed with Mark Henry in a winning effort against the teams of Darren Young and Damien Sandow, The Dudley Boyz and The Ascension. As a result of the win, Swagger qualified for the Royal Rumble match itself during the main show; entering as the 24th entrant, only to be quickly eliminated by Brock Lesnar, lasting only 16 seconds. At Roadblock, Swagger would be defeated by Chris Jericho. At WrestleMania 32, Swagger would compete in the Andre the Giant Memorial Battle Royal, which was won by Baron Corbin. On the June 6 episode of Raw, Swagger faced long-time rival Rusev in Swagger's home state of Oklahoma in a losing effort via count-out. After the match, Swagger attacked Rusev before leading the crowd in a "We the People" chant. On the July 4 episode of Raw, Swagger was part of the main event, where he teamed with "Team USA", which consisted of himself, Big Show, Kane, Apollo Crews, Mark Henry, Zack Ryder and the Dudley Boyz, in a 16-man elimination tag team match, in which their team was victorious over "The Multinational Alliance", which consisted of Kevin Owens, Chris Jericho, Sami Zayn, Cesaro, Sheamus, Alberto Del Rio and The Lucha Dragons (Kalisto and Sin Cara).
In the 2016 WWE draft, Swagger was drafted to the Raw brand. On the September 12 episode of Raw, Swagger faced Jinder Mahal in a losing effort. After the match, Tom Phillips revealed to Swagger that his "Raw contract" expired soon, in which Swagger ignored Phillips and walked away. The following night, he switched brands on SmackDown, interrupting Baron Corbin and stating that he has signed exclusively to the brand. Swagger defeated Corbin on the October 4 episode of SmackDown after the referee thought he submitted when he was actually trying to reach the bottom rope. Corbin would then defeat Swagger twice, at the No Mercy pay-per-view and again on the October 18 episode of SmackDown, ending the feud.
On March 13, 2017, it was announced that WWE had granted Swagger his release.