Jester debuted in 1998. He won the
Scottish Heavyweight Championship from Johnny Moss in 2007. He beat Mikey Whiplash for the
ICW Heavyweight Championship in 2013, holding it for 385 days with defences against
Sabu,
Fergal Devitt,
Joe Coffey,
Grado,
Wolfgang,
Jimmy Havoc,
Big Damo,
Mark Coffey and
Martin Stone before losing the title to
Drew Galloway in 2015. Jester received two rematches but was unsuccessful. On ICW: Fight Club in 2018, Jester and
Sha Samuels defeated
Rampage Brown and Ashton Starr for the
ICW Tag Team Championships before losing them back to Brown and Starr at ICW: Fear & Loathing XI. On 8 August 2022, Jester defeated Andy Wild, Krieger and Jason Reed to become number one contender to the ICW World Heavyweight Championship but was defeated by champion
Kez Evans at ''ICW: Shug's Hoose Party 7.'' ==Acting career==