[2] Caster trained under Brian Myers and Pat Buck at their Create A Pro Wrestling Academy and made his debut for the school's promotion in February 2015, later becoming the inaugural CAP Champion in December of that year.

[1] Caster made his first appearance for All Elite Wrestling (AEW) on the June 23, 2020 episode of Dark as a heel, teaming with Luther and Serpentico in a losing effort against Jurassic Express (Jungle Boy, Luchasaurus and Marko Stunt).

[3] He came back with his new tag team partner Anthony Bowens on the October 27 episode of Dark but lost to Best Friends (Chuck Taylor and Trent).

[11] On the August 3 episode of Dark, while making his entrance, Caster rapped about subjects such as Olympic gymnast Simone Biles' mental health issues, the Duke lacrosse case, the validity of PCR COVID-19 testing, and made a sexual joke about Julia Hart.

[14][15] The Acclaimed then began a feud with The Young Bucks, defeating them on the June 19 episode of Dynamite, in a eliminator match to earn a future shot at the AEW World Tag Team Championship.

On the August 14 episode of Dynamite, The Acclaimed's title match against The Young Bucks ended in a disqualification loss due to interference from FTR.

[19] On January 18 at the Collision edition of Maximum Carnage, Caster cemented his heel turn and disbanded The Acclaimed after Bowens chose to side with Gunn over him.