In 2006, Hager had a WWE tryout in Deep South Wrestling, and in September 2006, Hager made his in-ring debut for Deep South Wrestling defeating Antonio Mestre in a dark match.[3][9] He competed mainly in dark matches, before being moved to Ohio Valley Wrestling in January 2007.[10] He started for OVW, by defeating Atlas DaBone, and in the following months began a rivalry with K.C. James[11][12][13] Hager began teaming with a multitude of opponents to feud with James and his tag team partner Cassidy James.[14][15]
In August 2007, Hager went back to Florida Championship Wrestling, where he began a rivalry with TJ Wilson.[3][16][17] On February 15, 2008, Hager defeated Ted DiBiase, Jr. in Tampa, Florida at the Florida State Fair to become the first-ever FCW Florida Heavyweight Champion.[18] Earlier in the night, DiBiase and Hager were the final two men remaining in a 23-man battle royal to determine the two championship contenders.[19]
On September 9, 2008, Hager made his start on the ECW brand under the ring name Jack Swagger, winning a match against a local wrestler.[22] He quickly made himself a villain when he did not let the referee hold up his arm after the win, and later started a rivalry with Tommy Dreamer by attacking him after Dreamer had saved Chase Stevens from Mike Knox.[23] He later defeated Dreamer in a wrestling match[24] and an "All American Challenge" competition.[25] After weeks of fighting, the two ended their rivalry in an Extreme Rules match, which Swagger won to extend his undefeated streak.[26] He then set his sights on Matt Hardy's ECW Championship, and was named the number one contender on the December 30, 2008 edition of ECW.[27] On the January 13, 2009 episode of ECW, Swagger defeated Hardy to win the ECW Championship, which is his first title in WWE."ECW Spoilers from Sioux City featuring Matt Hardy vs. Swagger for the title". The Wrestling Observer. 2009-01-12. Archived from the original on 2010-04-07. Retrieved 2009-01-13.</ref> His undefeated streak in singles matches ended on the February 3 episode of ECW, when he lost to Finlay.
World Heavyweight Championship run and SmackDown (2010)
On the March 1 episode of Raw, Swagger beat Santino Marella to wrestle in the Money in the Bank ladder match at WrestleMania XXVI.[28] At WrestleMania, Swagger won the Money in the Bank ladder match, winning a contract for any WWE world championship that he could use at any time over the next year.[29] On the episode of Raw after WrestleMania, Swagger tried to cash in his Money in the Bank contract on John Cena, but changed his mind when he saw that Cena was not hurt enough for Swagger to beat. As the match had never started, Swagger kept the contract for use at a future date.[30]
Swagger cashed in his Money in the Bank contract during the SmackDown taping on March 30, 2010, after the World Heavyweight ChampionChris Jericho had been speared by Edge.[31] Swagger went on to defeat Jericho to win the World Heavyweight Championship for the first time.[31][32] after his championship win, Swagger changed into a more serious Swagger which was different from his last persona, where he was known for doing pushups and beating his chest during his ring entrance. He 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.[33] At Over the Limit, Swagger kept the title against The Big Show by disqualifying himself.[34] At the Fatal 4-Way pay-per-view on June 20, he lost the championship to Rey Mysterio in a fatal four-way match, which also had CM Punk and The Big Show.[35]