Whipwreck made his Extreme Championship Wrestling (ECW) debut on the February 1, 1994 episode of Extreme Championship Wrestling, where he teamed with Keith Shearer in a tag team match against Kevin Sullivan and The Tazmaniac. Whipwreck continued to make appearances as an enhancement talent for the next three months on Extreme Championship Wrestling.
On the May 17 episode of Extreme Championship Wrestling, Whipwreck defeated The Pitbull to win the World Television Championship, his first title in ECW. Whipwreck was heavily pushed upon his debut as a fan favorite underdog character. He made his first televised title defense against Kevin Sullivan on the May 24 episode of Extreme Championship Wrestling, where Whipwreck won by disqualification. He made a successful title defense against 911 by disqualification at the When Worlds Collide event. Whipwreck soon entered a feud with Jason after Jason interfered in Whipwreck's title defenses against Rockin' Rebel at Hostile City Showdown and Chad Austin at Heat Wave and assaulted him during his matches. Whipwreck dropped the World Television Championship to Jason in a no disqualification match at the Hardcore Heaven event on August 13 when The Pitbulls attacked Whipwreck.
Two weeks later, Whipwreck substituted for Terry Funk and won the World Tag Team Championship with Cactus Jack by defeating The Public Enemy (Johnny Grunge and Rocco Rock). The duo held the titles until November to Remember, where they lost the titles back to Public Enemy. Whipwreck closed the year with a win over Don E. Allen at Holiday Hell in December. Whipwreck continued his rivalry with Jason in early 1995 and formed a tag team with Hack Meyers. Whipwreck and Meyers lost to Jason and Paul Lauria in a tag team match at Return of the Funker on February 25. The duo soon began a feud with Raven's Nest after Whipwreck defeated Stevie Richards at Hostile City Showdown. Whipwreck joined forces with Raven's Nest rival Tommy Dreamer to take on Raven and Stevie Richards in a tag team match at Enter Sandman, which Whipwreck's team lost.
Whipwreck began to ascend the ranks, while also expanding his moveset in the meantime. He received his first major main event push on the August 1 episode of Hardcore TV when he won a battle royal by lastly eliminating Marty Jannetty to become the number one contender for the World Heavyweight Championship. Later that night, he was unsuccessful in his title shot against The Sandman. Whipwreck began feuding with Sandman over the title. He defeated Sandman in a Singapore cane match at Wrestlepalooza. At Gangstas Paradise, Whipwreck teamed with Public Enemy against Sandman, New Jack and 2 Cold Scorpio in a Gangstas Paradise match, which Whipwreck's team won. On the October 31 episode of Hardcore TV, Whipwreck defeated Sandman in a ladder match to win the World Heavyweight Championship, becoming and a Triple Crown Champion in ECW. Whipwreck successfully defended the title against Steve Austin at November to Remember. At December to Dismember on December 9, Whipwreck defended the title against Sandman and Austin in a three-way dance, where Whipwreck was the first to be eliminated by Austin. Sandman won the title.
Whipwreck continued his championship success at the Holiday Hell tour on December 29, when he defeated 2 Cold Scorpio in a Winner Takes All match to win Scorpio's World Television Championship and the World Tag Team Championship (which Scorpio held with Sandman), with assistance by former tag team partner Cactus Jack, who delivered a double underhook DDT to Scorpio and put Whipwreck on top of him for the pinfall. Whipwreck was dissatisfied with the title win but Jack chose himself as Whipwreck's other half of the World Tag Team Champions. Whipwreck lost the World Television Championship back to Scorpio at House Party on January 5, 1996, after interference by Raven.
Whipwreck and Cactus were unable to maintain a successful partnership due to Cactus's dirty tactics. The duo dropped the World Tag Team Championship to The Eliminators (Perry Saturn and John Kronus) on the February 6 episode of Hardcore TV. After the match, Cactus turned on Whipwreck with the aid of Raven and Whipwreck began feuding with Cactus. At CyberSlam, Whipwreck cost Cactus a match against Shane Douglas, setting a match between the former tag team partners at Big Ass Extreme Bash, which would turn out to be Cactus' farewell match in the company. Whipwreck was defeated following several chair shots and a piledriver.
At CyberSlam, Whipwreck began a new angle with Taz by picking up a fight with him after Taz continued to assault his defeated opponent Joel Hartgood after the match, but Whipwreck was taken down with a Tazmission. Whipwreck lost to Taz in a series of matches including one at Big Ass Extreme Bash on March 8. At Heat Wave, Whipwreck attempted to regain the ECW World Tag Team Championship from The Eliminators with Sabu as his partner but failed to win the titles. Whipwreck appeared on the February 24, 1997 episode of Monday Night Raw, emanating from ECW's home arena Manhattan Center, where he lost to Taz as part of an angle between ECW and the World Wrestling Federation (WWF). He took a hiatus from ECW for the next few months until returning to television on the May 29 episode of Hardcore TV, where he and Spike Dudley lost to Big Dick Dudley and D-Von Dudley. Whipwreck and Dudley began teaming together and got involved in a feud with PG-13. Whipwreck and Dudley lost to PG-13 at the Orgy of Violence event, but defeated PG-13 and Whipwreck's longtime rival Jason in a handicap match at July's Heat Wave pay-per-view.
Whipwreck was next placed in a rivalry with the undefeated newcomer Justin Credible, who was being managed by Jason. Whipwreck faced Credible in a match at November to Remember, which Whipwreck won by pinning him after a Whipper-Snapper, ending Credible's televised winning streak. Whipwreck disappeared from television and returned at the Living Dangerously pay-per-view on March 1, 1998, where he helped Tommy Dreamer in beating Credible. Whipwreck lost to Credible in a rematch at May's Wrestlepalooza. He competed against Rob Van Dam for the ECW World Television Championship at It Ain't Seinfeld, where the match ended in a no contest after Sabu interfered and attacked Van Dam. Whipwreck would then compete against Sabu in a series of matches throughout the year. His last rivalry in the company was against Jerry Lynn. He defeated Lynn in the opening match of UltraClash on September 19. His last televised match in ECW was a loss to Lynn on the December 17 episode of Hardcore TV.
Whipwreck left ECW for World Championship Wrestling (WCW) in late 1998. He made his surprise WCW debut at the Uncensored pay-per-view in March 1999, unsuccessfully challenging Billy Kidman for the Cruiserweight Championship. He made only three more pay-per-view appearances. He would lose to Scotty Riggs at Spring Stampede and Van Hammer at The Great American Bash. His final WCW pay-per-view match was a Junkyard Invitational at Bash at the Beach. He left WCW after several months. While in WCW, he generally wrestled in the cruiserweight division or competed against fellow ECW alumni in the hardcore division. His last match was a draw against Chase Tatum on the August 23 episode of Monday Nitro.
Whipwreck returned to the ECW in October 1999, making his televised return to the company on the October 31 episode of Hardcore TV. He was brought back to the company by Lou E. Dangerously and faced Mike Awesome for the World Heavyweight Championship but lost. Whipwreck unsuccessfully challenged Rob Van Dam for the World Television Championship on the December 26 Hardcore TV. In 2000, Whipwreck faced C.W. Anderson in a losing effort at Guilty as Charged.
Whipwreck competed as a mid-carder, aligning himself with The Sinister Minister, during which his character was changed from a lovable loser to a mad-pyromaniac. During this time, he began competing against lighter wrestlers in the cruiserweight division. He competed in elimination matches at May's Hardcore Heaven and July's Heat Wave pay-per-views. During this time, he frequently feuded with Little Guido and joined forces with Yoshihiro Tajiri. Whipwreck and Tajiri formed a tag team called The Unholy Alliance. The duo entered a tag team tournament for the vacant ECW World Tag Team Championship. They defeated Full Blooded Italians (Little Guido and Tony Mamaluke) in the quarter-final round, EZ Money and Julio Dinero in the semi-final round and the teams of Jerry Lynn and Tommy Dreamer and Simon Diamond and Johnny Swinger in the final round, a three-way dance to win the vacant titles. The Unholy Alliance dropped the belts to Full Blooded Italians on the September 8 episode of ECW on TNN. The Unholy Alliance unsuccessfully challenged The FBI for the tag titles at Anarchy Rulz. The duo got another opportunity for the titles at November to Remember, where Whipwreck was injured in the match and was replaced by Super Crazy.
This marked the beginning of a brief alliance between Super Crazy and the Unholy Alliance, which ended after the trio lost to Hot Commodity (EZ Money, Julio Dinero and Chris Hamrick) in a six-man tag team match on the November 19 episode of Hardcore TV. The Unholy Alliance turned on Crazy when Whipwreck helped Tajiri in defeating Crazy in a match by delivering a Whipper-Snapper to Crazy, allowing Tajiri to get the win. The duo became villains in the process. The Unholy Alliance began feuding with Crazy and the duo defeated Crazy and his partner Kid Kash in a tag team match at Massacre on 34th Street. The Unholy Alliance defeated Crazy and Kash and Full Blooded Italians in a three-way dance at ECW's final pay-per-view Guilty as Charged on January 7, 2001. The Unholy Alliance won the match. This was his final match, as the company folded down due to bankruptcy after holding its final event on January 13.
At the first-ever ECW One Night Stand put together by WWE, Whipwreck, Yoshihiro Tajiri and The Sinister Minister reunited for one night only as Whipwreck and The Minister stood in Tajiri's corner during his three-way dance against Little Guido and Super Crazy. At the second ECW One Night Stand pay-per-view on June 11, 2006, Whipwreck was seen on camera celebrating with other ECW wrestlers after Rob Van Dam won the WWE Championship.