On October 30, 2007, he debuted in a losing effort to Shawn Osbourne under his real name Kevin Kiley, and later faced off with wrestlers like Sebastian Slater and Jack Gabriel.

[7] In early December, he underwent another name change, calling himself Alex Riley and developing the gimmick of a university jock, complete with a letterman's jacket as a part of his attire.

In mid-2009, he competed in several dark matches prior to Raw and SmackDown, wrestling against Jamie Noble, Montel Vontavious Porter and Jimmy Wang Yang, and also appeared at house shows.

[10] On March 18, 2010, Riley defeated Justin Gabriel and Wade Barrett in a triple threat match to win the FCW Florida Heavyweight Championship.

[12][13] At the July 22 FCW tapings, Riley lost the title to Mason Ryan in a triple threat match, also involving Johnny Curtis.

[37] Riley debuted on the April 29 episode of SmackDown by interrupting Randy Orton, but had an RKO performed on him before he could speak.

[48] The following night on Raw, Riley was one of the eight men placed in the WWE Championship tournament but lost to The Miz in the first round, ending their feud.

[49] On the August 1 episode of Raw, Riley began a feud with the United States Champion Dolph Ziggler, beginning with a verbal confrontation.

[55] For the remainder of 2011 after his return, Riley was largely relegated to appearing on Superstars, defeating the likes of Drew McIntyre and JTG.

[57] Riley claimed a rare victory on the May 2 episode of NXT when he teamed with Tyson Kidd to beat JTG and Johnny Curtis.

[58] After several months absence from television, he made his return on the July 3 episode of SmackDown in a World Heavyweight Championship Money in the Bank qualifying match against Dolph Ziggler, in a losing effort.

Riley ended his singles losing streak on August 6 episode of Raw by defeating Ziggler with a roll-up after a distraction from Chris Jericho on commentary.

[60] Riley next appeared on the April 17 episode of Main Event, competing in an 11-man battle royal to determine the number 1 contender for the Intercontinental Championship and surviving until the final four when he was eliminated by Primo.

Riley was a regular member of the expert panel on both the Raw and SmackDown pre-shows on the WWE Network, and also made several appearances on pay-per-view in this role.

In 2013 and 2014, Riley made occasional in-ring appearances at WWE live events, picking up untelevised wins over the likes of Tyson Kidd, Curt Hawkins and Heath Slater.

[63][64][65][66] Throughout late 2014 and early 2015, Riley started a Twitter campaign with the hashtag #FreeRiley, apparently in an attempt to get management to notice him and book him as an in-ring competitor, given that his last televised match was in 2013.

[68] After the match, Owens called Riley "the dumbest man in NXT" for returning to the ring and threatened to destroy his career.

[69] On March 29 at WrestleMania 31, Riley competed in the André The Giant Memorial Battle Royal but was eliminated by Damien Mizdow.

[72] Riley made his return from injury on the January 27, 2016 episode of NXT after eight months of inactivity, sporting longer hair and beard, in a winning effort against Bull Dempsey, turning heel for the first time since 2011.

[75] As "The Rare Breed" Kevin Kiley, he appeared for the National Wrestling Alliance (NWA) at their Nuff Said event on February 11, 2023, in a losing effort to EC3.

[79] He was arrested for DUI in Florida in November 2010,[80] yet the charges were dismissed in July 2011 after Hillsborough County Circuit Judge Dick Greco Jr. ruled that law enforcement did not have probable cause to stop Riley's vehicle and thus violated his fourth amendment rights against unreasonable searches and seizures.