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He first appeared in 2007, as a security guard during a brawl between John Cena and Umaga on Raw. He appeared again in a Raw dark match, at the TV taping on August 18, 2008, when he lost to William Regal. He also lost to D-Lo Brown in a dark match, before defeating Jamie Noble in a dark match prior to a SmackDown taping on August 29.

On September 9, 2008, Swagger made his debut on the ECW brand, winning a match against an enhancement talent. 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 jobber Chase Stevens. He later defeated Dreamer in a wrestling match and an "Amateur Wrestling Challenge" competition. After weeks of feuding, their rivalry ended in November in an Extreme Rules match, which Swagger won to extend his undefeated streak in ECW.

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. In 2009, on the January 13 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, to whom he lost the ECW Championship at Backlash, which ended his 104 day reign as champion. He attempted to regain the championship title in a singles match against Christian at Judgment Day and in a triple threat hardcore match at Extreme Rules, but was unsuccessful in both attempts. His attempt to win the ECW Championship at The Bash in a 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 WWE United States Championship. He had his first singles match for the championship on September 21 against Kofi Kingston, but lost the match by countout after stealing the championship and leaving the arena with it, although Kingston later took it back while Swagger was in a physical confrontation with The Miz. Swagger made another unsuccessful attempt at the championship at the Hell in a Cell pay-per-view in a triple threat match against Kingston and The Miz. On January 31, 2010 at the Royal Rumble, Swagger enter number 26 in the Royal Rumble match; Swagger was 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 the 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 pushups and beating his chest during his ring entrance. He successfully defended his championship 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 the Extreme Rules pay-per-view. At Over the Limit, Swagger retained the title against The Big Show by intentionally disqualifying himself.

At the Fatal 4-Way pay-per-view on June 20, he 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 & Chairs, Swagger competed in a triple threat ladder match for the WWE Intercontinental Championship against Kofi Kingston and Dolph Ziggler, in which the latter went on to win the match.

On the February 28 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 received 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. On May 1, 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 WWE 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 would continue to fight over Guerrero over 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 WWE United States Championship by defeating Zack Ryder. At Elimination Chamber, Swagger successfully defended his title against Justin Gabriel. On the February 27 edition of Raw, Swagger and Ziggler unsuccessfully challenged Primo and 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. On the following edition 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 edition of Raw, Swagger was announced as a member of Team Johnny at Wrestlemania XXVIII. On the April 2 edition 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. On the next Raw, he faced Ziggler in a match to see who Vickie Guerrero would still manage, but came short once again.

On the June 25 episode of Raw, Swagger unsuccessfully challenged Santino Marella for the United States Championship. On the June 29 edition of SmackDown, Swagger challenged Tyson Kidd in a Money in the Bank qualifying match, but was once again defeated. Following this loss, Swagger would go 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 be taking time off. On December 2, 2012 Swagger returned at a house show in Florence SC, competing in a triple threat match against Antonio Cesaro and R-Truth for the U.S. Championship. However, Swagger failed to win the title.

On the February 1, 2013 episode of SmackDown, Swagger returned, demanding SmackDown General Manager Booker T to put him in the Elimination Chamber match at the Elimination Chamber pay-per-view. Later on that night, Swagger made his in-ring return by defeating Kofi Kingston. On the February 11 episode of Raw, now accompanied by the xenophobic Zeb Colter as his manager, defeated Zack Ryder to earn a spot in the chamber, which he won by last eliminating Randy Orton.

On the March 18 episode of Raw, Swagger broke the ankle of 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. Swagger then suffered a hand injury which kept him out for several weeks. Swagger was announced as one of the participants in the 2013 World Heavyweight Championship Money in the Bank.

Swagger returned on the July 1 episode of Raw, accompanying Zeb Colter's new client Antonio Cesaro to his match with Cody Rhodes. On July 14 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. On September 15, 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 WWE 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. On the February 14th episode of SmackDown, Swagger became the #1 Contender for the Intercontinental Championship after winning a Fatal 4-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 Andre 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 Andre. Swagger retalied attacking Cesaro on the following RAW and then destroying the trophy, thus ending the stable. Swagger would feud with Cesaro, which also involved Rob Van Dam, resulting in the three men competing in a triple threat elimination match at Extreme Rules, which Cesaro won. The next night after Raw, Colter and Swagger would rant about foreign superstars in the WWE, when Adam Rose would make his WWE debut and interrupted the two men. The next night on Main Event, Swagger would lose to Dolph Ziggler with the distraction by Rose. Six days later on Raw, Swagger would lose to Rob Van Dam with another distraction by Rose. Their feud would culminate on the June 2nd episode of RAW where Rose defeated Swagger. On the June 23 episode of Raw Swagger would be named to compete in the Money in the Bank ladder at Money in the Bank. Swagger would not win the match, but would lose it to Seth Rollins.

On the June 30 episode of Raw, Swagger would turn face for the first time since debuting in the WWE after he and Zeb Colter confronted Rusev and Lana stating their actions of taking advantage of America's freedom which led to Swagger attacking Rusev. On the July 7 episode of Raw, Rusev sent a message to Swagger and Colter when he defeated Rob Van Dam via submission. On the July 14 edition of Raw, a United States-Russia Detente took place between Rusev and Swagger, Colter was concerned if Rusev would step up and face Swagger at Battleground in which Rusev accepted the challenge. At Battleground, Rusev defeated Swagger by countout. On the July 22nd edition of Main Event, Swagger defeated Rusev via disqualification. On the August 1st edition of Smackdown, a Flag match was announced between Swagger and Rusev, set to take place at SummerSlam. On the August 4th edition of Raw, Swagger and Zeb Colter confronted Rusev and Lana about the USA which led to Rusev attacking Swagger with the Russian flagpole. At SummerSlam, Swagger lost to Rusev by knockout. Just days after the SummerSlam event, Swagger earned another chance to face Rusev, this time in a regular singles match. Though he failed to get the victory due to outside interference from Bo Dallas, leading to a feud between the two heading into September's Night of Champions pay-per-view event. On November 10, he joined Team Cena in a match against Team Authority in Survivor Series, but was removed from the team following an injury. He later returned on November 18th on Main Event, losing to Bray Wyatt.

During the Survivor Series pre-show on November 23 2014, Swagger returned showing his support for Team Cena. He would face off against former rival Cesaro, who showed support for Team Authority. Swagger defeated Cesaro by submitting him with the Patriot Lock. At TLC, Swagger challenged Rusev for the United States Championship, but lost by submission. After this, Swagger continued his loss streak, losing on Main Event against Luke Harper, Bray Wyatt and even low-profile superstars like Titus O'Neil. He entered the Royal Rumble Match at Royal Rumble (2015) but was eliminated by The Big Show. Swagger finally picked up a singles win over Stardust on the 23 February edition of Raw, via submission due to Goldust distracting his brother. On SmackDown on February 26, Jack confronted Rusev about not accepting John Cena's rematch at WrestleMania 31, only to be taken down once again. Swagger participated in the 2nd Annual André the Giant Memorial Battle Royal at WrestleMania 31 but failed to win the match.

After losing matches to King Barrett on both Superstars and SmackDown, Swagger returned on the July 30 episode of Smackdown to enter contest against Rusev (with Summer Rae). The match would end with Rusev victorious after a long and hard-fought bout. Rusev would then try to attack Swagger after the match ended, but Swagger countered and gained the upper hand, causing Rusev to back away, which left Swagger standing tall. On 31st July, Swagger lost to King Barrett on an episode of Superstars. Swagger finally picked up a win against Bo Dallas on the August 7th episode of Superstars. Despite that, he lost to Big Show the next day on Main Event.

After more months of wrestling only on Main Event and Superstars, Swagger's manager Zeb Colter returned after almost a year-long hiatus at October's Hell in a Cell PPV. However, Colter seemed to cut all ties with Swagger as he announced the returning Alberto Del Rio as his new client and formed "MexAmerica", a nation combining both Americans and Mexicans. On the November 2 episode of Raw, Swagger encountered his former manager Zeb Colter, only to be interrupted by Del Rio. On the following week's SmackDown Swagger made the save as Del Rio was continuing to inflict punishment on Neville after Del Rio had already defeated the Englishman. This started a feud between the two, which culminated at TLC with Swagger being defeated by Del Rio with the United States Championship on the line. At the 2015 WWE Tribute to the Troops event, Swagger defeated Rusev by submission in a "Boot Camp" match.

On the New Years edition of WWE Superstars, Swagger teamed with Mark Henry to defeat The Ascension. On January 24, 2016 at Royal Rumble, during the kick-off show, Swagger continued his alliance 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 29 seconds. At WWE Roadblock on March 19, Swagger would be defeated by Chris Jericho. At WrestleMania 32, Swagger would once again be unsuccessful in winning the Andre the Giant Memorial Battle Royal. 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 he was shoved into Titus O'Neil, who was on commentary, at the count of nine. 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 (Bubba Ray Dudley and D-Von Dudley), 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).

On July 19, at the 2016 WWE Draft, Swagger was drafted to Raw. On September 13, Swagger became the first Superstar to jump ship during the New Era, joining SmackDown Live after his contract with Raw expired. He began a feud with Baron Corbin after interrupting him in his SmackDown Live debut. The following week, Swagger defeated Corbin under dubious circumstances after Corbin seemingly tapped out, even though he got to the ropes. An irate Corbin however beat Swagger by cheating at No Mercy. The rubber match took place on the October 18 SmackDown, when Corbin easily defeated Swagger.