[2] Pittman attended Freeport High School, where he was recruited to the Wrestling team by coach Terry Haise.

Back home, Pittman attended Nassau Community College where he also wrestled, again reaching the national championships where he was disqualified in the first match due to a bodyslam.

[5] After leaving the military, Pittman trained as a professional wrestler at the WCW Power Plant under Terry Taylor and The Assassin in 1993.

[7] He made his televised debut as one of the judges for Marquess of Queensberry Rules between Ric Flair and Lord Steven Regal on the April 30 episode of Worldwide.

[7] His character was repackaged in early 1995 and vignettes promoting his debut aired on television beginning with the February 19 episode of Worldwide.

After propositioning the likes of Jimmy Hart, Bobby Heenan, and Steve McMichael, Pittman connected with Teddy Long, turning face in the process.

[12] Pittman would go on to wrestle in WCW through the first 5 months of 1997, gaining opportunities at the United States Heavyweight Championship against Eddie Guerrero on Saturday Night on March 4, and his final match in WCW taking place on the 24th of May on Saturday Night, a shot at the World Television Championship against Lord Steven Regal.

Pittman arrived in Florida Underground Wrestling for several months finally coming out of retirement to defeat "The Cuban Assassin" Fidel Sierra.

Craig Pittman would receive a shot at the NWA World Heavyweight Championship, battling and losing to the champion at the time Dan "The Beast" Severn.

Vale Tudo Japan 1995 was well documented in the documentary Choke, a 98-minute film by filmmaker Robert Goodman which follows three of the participants (Rickson Gracie, Todd Hays and Koichiro Kimura) as they prepared for and fought in the event.

On October 1, 2011, Pittman competed at Real Fighting Championships 25 in Tampa Florida losing a Unanimous Decision to Rodney Bell.