DellaGatta was a longtime star of NWA New England and, following Tony Rumble's death in 1999, adopted the "Boston Bad Boy" gimmick in honor of his mentor.

DellaGatta also briefly served as the booker for NWA New England, succeeding Jeff Katz and Knuckles Nelson, and headed a second incarnation of Tony Rumble's "heel" stable The Brotherhood consisting of himself, Rick Fuller, and The DarkAngel.

[6][7] He also worked to establish himself as singles competitor and, on August 22, he defeated Jeff Mangles for the NWA New England Junior Heavyweight Championship in Somerville, Massachusetts.

[13] NWA New England began experiencing trouble booking events in 2002 and finally went on year-long hiatus following a fundraiser in Riverside, Rhode Island, for victims of the Station nightclub fire in April 2003.

He won a Ladder match in the main event in which the wrestler who could successfully retrieve Tony Rumble's batting helmet would become the new "Boston Bad Boy".

[2] In May, DellaGatta briefly lost the NWA New England Heavyweight Championship to Steve King in Melrose, Massachusetts[20] but regained it two weeks later remained champion for the rest of the year.

On October 2, 2002, DellaGatta lost to Lex Lovett a three-way match also involving Steve Madison for IPW Hardcore Wrestling at the Dallas Bull in Tampa.

AJ Styles and Mortimer Plumtree, on the pretense of scouting talent for TNA's "X-Division", unsuccessfully attempted to interfere on Reynolds' behalf and attacked DellaGatta after the match.

[38] NWA World Tag Team Champions America's Most Wanted (Chris Harris and James Storm) came out to stop the attack, however, a wild brawl ensued and ended up involving any wrestlers from the locker room to break it up.

[50] He did lose to NWA New England Brass Knuckles Champion Gino Martino in a number one contendership match for the NWH Heavyweight Championship on September 28, 2004, in Buxton, Maine.

[54] He also traveled overseas to the United Kingdom to defend his title against Phil Powers at a June 4 Revolution British Wrestling show at Ryan Hall in Chingford.

In September 2005, he took part in a Founder's Day benefit show for the Saugus public school system, organized by Everett-based wrestling academy Ringside Entertainment, appearing with Brutus "The Barber" Beefcake, Ebony Blade, Lollipop, and midget wrestler Short Sleeve Sampson.

On July 30, 2006, in Sanford, Maine, he was part of a 10-man elimination match teaming with Larry Huntley, Beau Douglas, Lotus, and Eric Atlas to defeat Osirus, Craig Trace, Loco, F.O., and Christian Sane.

[50] Two months later, he lost a three-way match against Matt Ledge and Beau Douglas for NWA New England X Division Championship at the Cardinal Shehen Center in Bridgeport, Connecticut.

[64] On November 25, 2006, at the 7th annual Tony Rumble Memorial Show in Saugus, Massachusetts, DellaGatta made NWA New England history by winning the promotion's heavyweight, Cruiserweight, and X-Division titles in a single night.

He first won a five-way match involving T.N.T., "Black Lotus" Matt Ledge, Paul Hudson, and Cameron Matthews to win both the Cruiserweight and X-Division titles.

Later on in the show, he won the "Tony Rumble Memorial Battle Royal", with the assistance of manager Johnny Fabulous, and went on to defeat Luis Ortiz and Slyck Wagner Brown in a Triple Threat match to win the heavyweight championship.

In May 2007, DellaGatta was one of several American independent stars which participated in MainStream Wrestling Entertainment's 6th annual "Sea Side Slam Tour" which visited 10 cities in Newfoundland and Nova Scotia over a two-week period.

[68] After NWA New England ceased operations, DellaGatta was brought into the Millennium Wrestling Federation where he aligned himself with Johnny Fabulous and The Uprising (Joey Mercury and MWF Tag Team Champions The Canadian Superstars - Dave Cole & J-Busta).

[69] At MWF's August 4 supercard "Soul Survivor IV" DellaGatta lost to Tiger Mulligan at the Good Time Emporium in Somerville, Massachusetts.

On April 18, he joined Sonny Roselli and Gary Wentzell in a 6-man tag team match to defeat Larry Huntly and The Latin Hit Squad in Mexico, Maine.

[82] In singles competition, he faced Lance Cade and NWA On Fire Heavyweight Champion "Golden Boy" Bobby Robinson in August,[83] and "The Maine Mauler" Cousin Larry in September.

It was there that he formed the "Crown Jewels" with Darling Damon, a "flamboyant" pair in the style of the Christopher Street Connection or the WWE's Billy and Chuck.

where they were part of a special 8-man survival match with Ryan Matthews and "The Talent" T.J. Richter against Team Nightmare (Evan Siks, Nick Steel, Lil' Nicky Amaral and Frankie Vain).

On November 29, 2008, The Crown Jewels won via forfeit at "Double Intensity" when Chase Del Monte and Fred Curry, Jr. failed to appear at the referee's ten count; they subsequently faced Team Nightmare in a match which ended in a double-disqualification.

[88] DellaGatta's original opponent was Nick Steel but was unable to appear at the show when someone slashed the tires of his car and Evan Siks took his place.

[91] The 2-day "Autumn Unleashed" show on October 23–24 saw The Crown Jewels on the run from their rivals; on the first night in Somerset, they lost to Davey Loomis and Alex Payne via countout and, in a non-title match, to Don Vega and Ryan Bisbal in Quincy.

[103] He was also booked to wrestle a benefit show for retired wrestler Maxx Lethal, whose wife suffers from liver problems, prior to its sudden cancellation by the board of selectmen of Framingham, Massachusetts.

[105][106] On December 16, 2011, DellaGatta made a surprise return to New England Championship Wrestling for its year-end supercard "The Fight Before Christmas" at the Millerville Men's Club in Blackstone, Massachusetts.

He also discussed plans to host a bi-monthly talk show of his own, "The Rumble Seat", and speculated on developing an undercover "whistleblowing" tv series to expose local political corruption.