[1] As a child, he loved professional wrestler "Macho Man" Randy Savage,[12] with other favorites including Curt Hennig, Davey Boy Smith, and Frank Gotch.

[10] Beginning January 2012, the company's YouTube channel hosted a series called The Sisterhood of the Traveling Tights where Castle interviewed professional wrestlers.

[24] During 2009 in Next Era Wrestling (held in The Auditorium Center in Rochester, New York) after defeating Brett Mednik (April 18)[25] and Brandon Thurston (June 20)[26] he unsuccessfully challenged Josh Jordan (the Northeastern Champion) on July 18 but they later team together.

[29] Remarkably, on May 9, 2015, he faced Tommy Dreamer for the title in a four-way elimination match that also included RJ City and Justin LaBar, but was defeated.

[34] He would become quite popular with Chikara fans over the duration of that season, and would end the year with a successful victory over Juan Francisco de Coronado, in a German suplex match.

[45] After a win over Takaaki Watanabe on the July 8 episode of Ring of Honor Wrestling,[46][unreliable source] Castle lost to Adam Cole at Death Before Dishonor XIII.

[59] Castle would then compete in high-profile matches against ROH's partner New Japan Pro-Wrestling talent Kazuchika Okada at Death Before Dishonor XIV,[60] and Kushida at Field of Honor.

[63] Castle then participated in the 2016 Survival of the Fittest, defeating Chris Sabin and Rhett Titus in the first round,[64] to qualify for the six-man mayhem in the final, which he failed to win.

On the November 19 episode of Ring of Honor Wrestling, Cabana turned on Castle by attacking him and The Boys, thus splitting up the tag team.

[66] At the 15th Anniversary Show pay-per-view on March 10, 2017, Castle and The Boys unsuccessfully challenged The Kingdom (Matt Taven, T. K. O'Ryan and Vinny Marseglia) for the ROH World Six-Man Tag Team Championship.

[74] Shortly after the title loss, Castle achieved major success in singles competition, by participating in the Soaring Eagle Cup tournament, which he won by defeating Flip Gordon in the first round, and Frankie Kazarian, Matt Taven and Silas Young in the final, a Four Way Elimination match.

[77] Castle made his first successful title defense against the 2017 Survival of the Fittest winner Punishment Martinez on the February 11, 2018 episode of Ring of Honor Wrestling.

[78][79] He would make his second title defense against Beretta and Beer City Bruiser in a three-way match at Honor Rising: Japan.

[84] Castle suffered a back injury during this time,[85][86][87] forcing him to drop the title to Jay Lethal in a four corner survival match, also involving Cody and Matt Taven, on the July 21 (taped June 30) episode of Ring of Honor Wrestling.

[88] Castle returned to ROH from his injury in October,[89] and participated in the 2018 Survival of the Fittest,[90] competing against Colin Delaney and Hangman Page.

[106] At Honor For All, Castle began teaming with Joe Hendry by defeating Shinobi Shadow Squad (Cheeseburger and Eli Isom).

[108] Castle then participated in a tournament to determine the #1 contender for the ROH World Championship at Final Battle,[109] defeating Mark Haskins in the first round,[110] before losing to eventual winner PCO in the semi-final at Glory By Honor XVII.

[111] Castle continued to team with Hendry, losing to 2 Guys 1 Tag (Josh Woods and Silas Young) at Final Battle.

[112] Castle and Hendry teamed in various matches during late 2019 and early 2020,[113][114][115][116][117] before splitting up as ROH went on a hiatus during the outbreak of the COVID-19 pandemic in the United States.

[123] On the April 24 episode of Ring of Honor Wrestling, Castle interrupted a match between Dak Draper and Eli Isom to recruit them as his proteges to improve the showmanship of ROH.

[128] On the November 21 episode of Ring of Honor Wrestling, Castle defeated Dragon Lee to win the World Television Championship after assistance by Draper.

[129] However, at Final Battle in December 2021, Castle lost the title to Rhett Titus in a four corners survival match, also involving Joe Hendry and Silas Young.

[132] Castle made his AEW debut at Battle of the Belts II on April 16, 2022, where he unsuccessfully challenged Jonathan Gresham for the ROH World Championship.

[135] At Death Before Dishonor in July 2022, Castle and the Boys defeated The Righteous (Vincent, Bateman, and Dutch) to win their second ROH World Six-Man Tag Team Championship.

[142] At Death Before Dishonor, Dalton Castle pressed Samoa Joe before outside interference from Stokely Hathaway prevented a clean finish to the match.

[147] On July 13, 2024 episode of AEW Collision, Castle lost to Roderick Strong in a match to determine who would face Mark Briscoe for the ROH World Championship at Death Before Dishonor.

[149][150] Castle's gimmick is that of a flamboyant showman with an androgynous personality, drawing comparisons to Gorgeous George,[12][151] Adrian Street, Ric Flair, and Goldust.

Castle has also mentioned glam rock stars David Bowie, Freddie Mercury, The Darkness, and Foxy Shazam as inspirations,[12] in addition to Lady Gaga.