Gentleman Jack Gallagher

In the following months, Gallagher would find himself in a losing streak, and after losing to Angel Garza on 29 November episode of 205 Live, he would headbutt General Manager Drake Maverick, thus turning heel again in the process. Gallagher returned on 28 February 2020 episode of 205 Live, attacking Lio Rush, while sporting a beard, shorter hairstyle and new tattoos covering his body. With his new attitude, Gallagher would develop a winning streak on 205 Live defeating the likes of Tyler Breeze and Oney Lorcan. On 10 April 2020 Gallagher was announced for the Interim Cruiserweight Championship Tournament representing Group B in the tournament. Gallagher lost to El Hijo del Fantasma and Akira Tozawa but was able to defeat Isaiah "Swerve" Scott to secure one win in the tournament.

Claffey has a 2-0 record as an amateur MMA fighter under the name Jack Claffey. A May 2019 report by the Wrestling Observer Newsletter alleged that there was interest from Bellator MMA about possibly recruiting Claffey for the promotion.

Gallagher regularly appears on Austin Creed’s YouTube channel UpUpDownDown, under the moniker 'Swagatha Christie'. In May 2019, Gallagher defeated Sarath Ton, Aka Pro Wrestler Mikaze, in a game of UFC 3 to win Mikaze's UpUpDownDown Championship. Gallagher lost the title to Kofi Kingston in a game of Mortal Kombat 3.

In June, Gallagher entered a feud with The Brian Kendrick, with Kendrick impersonating and mocking Gallagher after the latter's matches. Their feud ended on the 29 August episode of 205 Live, in which Gallagher was defeated by Kendrick in a no disqualification match. On 12 September episode of 205 Live, Gallagher attacked Cedric Alexander during his match with The Brian Kendrick, turning heel in the process. To reflect his turn, Gallagher stopped wearing his fluorescent trunks and began wrestling in a full suit instead. He also switched to a more technical, ground-based style and began using the umbrella as a weapon. In June 2018, Gallagher and Kendrick formed an alliance with Drew Gulak. On 3 October episode of 205 Live, Gallagher and Gulak attacked Kendrick, calling him the "weakest link" in the faction. On 31 October episode of 205 Live, Gallagher was defeated by Kendrick after Akira Tozawa prevented the interference from Gulak. The two sides went on to trade victories over the next few weeks. On 19 December episode of 205 Live, Gallagher and Gulak were defeated by Kendrick and Tozawa in a Street Fight to end the feud. Starting in February 2019, Gallagher and Gulak attempted to recruit the debuting Humberto Carrillo to their faction while also trying to prevent him from using high flying moves and instead using a more ground based offence. On 9 April episode of 205 Live, after Gulak attacked Carrillo during his match with Gallagher, Gallagher came to the aid of Carrillo and headbutted Gulak out of the ring, turning face in the process.

On 29 November, on the inaugural episode of 205 Live, Gallagher made his debut, defeating Ariya Daivari. On the 5 December episode of Raw, Gallagher defeated Daivari. On 27 December episode of 205 Live, Gallagher and Daivari participated in a Gentleman's Duel, where both men chose a weapon for their opponent and began the match back to back before moving five paces away from each other, but Daivari attacked Gallagher while his back was turned until Gallagher attacked him with a headbutt, causing Daivari to forfeit the duel. Their rivalry concluded in an "I forfeit" match on the 17 January 2017 episode of 205 Live, which Gallagher won. On 29 January at the Royal Rumble event, Gallagher participated in the annual Royal Rumble match and was eliminated by Mark Henry. On 7 February episode of 205 Live, Gallagher defeated Cedric Alexander, Mustafa Ali, Noam Dar, and T.J. Perkins in a fatal five-way elimination match to become the number one contender for the WWE Cruiserweight Championship. At Fastlane, Gallagher faced Neville for the title in a losing effort. Gallagher made a guest appearance on the 26 April episode of NXT, unsuccessfully challenging Tyler Bate for the WWE United Kingdom Championship in the main event.

On 24 April 2016, Gallagher earned a place in the WWE Cruiserweight Classic by defeating Pete Dunne in a qualifier match at Progress Wrestling's Chapter 29. On 3 August, Gallagher defeated Fabian Aichner in his first round match, but was eliminated from the tournament by Akira Tozawa in his second round match.

The rivalry between Gallagher and Banks continued into 2015 and at Back With A Bang, Banks picked up the win to end the feud. Following a loss to Chris Ridgeway at "Cruel Summer", Gallagher took another hiatus from Grand Pro.

Gallagher made his Grand Pro return at the 2013 Crazy Cruiser 8 where he defeated Bubblegum in the Quarter Finals before being pinned by eventual winner El Ligero in the Semi-Finals. At the start of 2014, Gallagher was defeated by CJ Banks at "Back With A Bang", the beginning of a rivalry.

On 3 March 2013, he made his debut for Pro Wrestling Zero1 in Japan, under the ring name Jack Anthony. He joined a tag team match alongside Ikuto Hidaka. On 15 April 2013, Anthony came together with Craig Classic, James Raideen, Jason New, Maybach Beta, Sebastian Concrete, Steven Walters and Tama Williams to form a gaijin stable named "New Age Wrestling Future" (NWF) under the guidance of Akebono. The stable was shortly afterwards joined by Jonathan Gresham and Mark Coffey.

Claffey, performing as Jack Toxic, made his singles debut at Grand Pro Wrestling West Park Fun Day and lost to Scarlett Web. Between March and April, Toxic tried to qualify for the Crazy Cruiser 8 2008 but failed multiple times; however, he won the Last Chance Saloon battle royal and therefore qualified for the tournament. On 2 May, he lost to El Ligero in the quarter finals. At Justice For All, he defeated Bubblegum in a rumble qualifying match but was eliminated from the rumble. At Guts & Glory, he returned under the name Jack Gallagher to compete in a four way scrabble match for the GPW British Championship and lost. At Battlefield, he lost a thirty-minute iron man match involving Zack Diamond and Mikey Whiplash for the GPW British Championship; however, next month at Heroes & Villains, he defeated Diamond for the title. He held the championship until Do Or Die, in December, where he lost it to Ste Mann. Gallagher introduced his own belt but lost it to Ste Mann, and took a 12-month break from Grand Pro.

On 8 June 2008, Claffey as Toxic, took part in the Lotto-Thunder Tournament and reached the semi final where he was defeated by Jack Domino. On 13 September, he participated in the FSW Trophy Tournament 2009 and was eliminated in the first round by Sparx. In 2010, he began using the ring name Jack Gallagher. At Futureshock #48, Gallagher won the FSW Trophy Tournament 2010 when he defeated Dave Breaks in the final. On 6 November 2011, Gallagher defeated Dave Rayne to become the FSW Champion. He would hold the championship for fourteen months before losing it to Davey Richards at Futureshock #61. At Futureshock #62, he defeated Stixx and Zack Gibson to become the number one contender for the FSW Championship. Chris Egan announced that Gallagher would be facing Sonjay Dutt at FutureShock #74, but Gallagher instead faced Jay Lethal at FutureShock #74. At the event, Gallagher defeated Dutt by pinfall.

In the beginning of 2007, Toxic and Cyanide teamed up and eventually became Lethal Dose. They became a regular attraction at Futureshock, appearing on many shows. The team would have their first title shot at Grand Pro Wrestling's That's Entertainment when they took on WKD for the GPW Tag Team Championship. The team traveled to Real Deal Wrestling and, in February and April had two chances to become the RDW Tag Team Champions, but lost both times. They then went to Hull to wrestle for New Generation Wrestling where they won all their matches. With this run of success, they returned to Futureshock at Futureshock #27 and defeated three other teams to become the first FSW Tag Team Champions. However, they lost the titles to The Doogooders at Futureshock #29. They returned to GPW at Livin' On The Edge to take part in a number one contendership four-way elimination match and lost. For the rest of 2009, they continued to team up but found little championship success and split up.

Claffey was trained by Alex Shane and the Futureshock staff. He made his professional wrestling debut at the age of 16 on 4 November 2006 at Futureshock #11, under the ring name Jack Toxic, teaming up with Alex Cyanide, Danny Hope, and Kris Travis. They defeated El Ligero, Charity, Faith, and Jamal Lewis. He also trained in grappling, a catch wrestling style, at The Snake Pit in Wigan, Greater Manchester. He received further training from Snake Pit alumnus Billy Robinson in the United States.

Oliver Westfield Claffey (born 7 January 1990) is an English professional wrestler and mixed martial artist currently signed to WWE, where he performs on both the NXT and 205 Live brands under the ring name Gentleman Jack Gallagher.