In February 1999, Quinlan entered the Killer Kowalski Professional Wrestling School in Malden, Massachusetts. Among the alumni of this school are Big John Studd, Triple H, Chyna, Perry Saturn, John Kronus and Matt Bloom. During this time Quinlan trained along with April Hunter, Aaron Stevens, Wagner Brown and Christopher Nowinski under the stage names Joseph Bagwell and Alex Bagwell which were assigned to him by promoters. On November 26, 1999, in his first professional wrestling match for the World Wrestling Alliance (Massachusetts), Quinlan teammed up with Aaron Stevens and Smooth Operator under the name Joseph Bagwell in a Six-Man Tag team match in Farmington, New Hampshire. In the Summer of 2000, Quinlan was briefly managed by Rocky Raymond while participating in Extreme based professional wrestling throughout New England. On July 2, 2000, while wrestling at the Thompson International Speedway in Thompson, Connecticut, Quinlan received a Powerbomb from his opponent through a table on concrete outside the ring fracturing one of the vertebra in his lower back which took months to heal. During this time Quinlan participated in photoshoots for New England-based Fitness features and on one occasion modeled for the Boston sports drink "Energy Bomb". Quinlan often felt he was exploited by promoters who forced him to use the Alex Bagwell gimmick (cousin of Buff Bagwell) against his wishes for their own financial gains. Oftentimes he would see less than half of his total income earned at a pro wrestling event which would ultimately force him to drop that gimmick and wrestle under the names Shane O' Kane and John Quinlan. Quinlan has often been misunderstood by many as having an ego and for being arrogant based upon his outside physical appearance which consists of numerous tattoos and scars when in reality he is a relatively shy and humble person. In the Fall of 2000, Quinlan was in contact with Joey Styles of Extreme Championship Wrestling (ECW) for a scheduled professional tryout which never materialized. Quinlan began training at World Gym in Lynnfield, Massachusetts with his manager Peter Karalekas in December of that same year. Early in 2001, he had a brief feud with Rick Fuller, formally of World Championship Wrestling (WCW), while wrestling for the National Wrestling Alliance of New England over a title shot against Fuller that ended in a loss. Shortly after, with Peter Karalekas, Quinlan went to Atlanta, Georgia and met with Ernest Miller (The Ayatollah in the 2008 movie The Wrestler) who was accompanied by Carmel Macklin and Michael Jai White about entering the WCW Power Plant. The WCW Power Plant unfortunately closed shortly after in March 2001 when WCW was purchased by the World Wrestling Federation. Quinlan began using the Shane O'Kane gimmick at this time which was developed by Peter Karalekas. The character initially portrayed an Irish thug from the mean streets of Hell's Kitchen, Manhattan, New York as a Heel (professional wrestling) but was transitioned to a masked wrestler as a Face (professional wrestling). He began training with Edward Leslie, who is best known as World Wrestling Entertainment (WWE) legend Brutus "The Barber" Beefcake, in the summer of 2001. Quinlan and Leslie trained at World Gym in Somerville, Massachusetts and traveled together wrestling for multiple professional wrestling organizations throughout the United States. Along with Leslie, Quinlan wrestled on cards with pro wrestling superstars such as King Kong Bundy, Jimmy Snuka, The Honky Tonk Man, Tito Santana and Tony Atlas. In late August 2001, Quinlan's pro wrestling future, together along with Leslie, looked bright with Jimmy Hart's newly founded Xcitement Wrestling Federation (XWF) as Shane O'Kane but it ultimately fell through for financial reasons. In December 2001, Quinlan and Leslie appeared together in a television commercial for World Gym in Lynnfield, Massachusetts. Quinlan's last professional wrestling match was with Empire Pro Wrestling on the independent circuit in the Spring of 2002.
- Signature moves
- The Irish Bad Boy (as Shane O'Kane)
- IIXtreme Hardcore Champion (1 time)
- IIXtreme Heavyweight Champion (1 time)