Charlie Dempsey stands as a compelling figure in the world of professional wrestling, blending technical prowess with a no-nonsense attitude that echoes the old-school greats while carving out his own path in WWE’s NXT brand. At just 28 years old, Dempsey has already achieved milestones that many wrestlers chase for decades, including multiple reigns as the NXT Heritage Cup Champion. His influence extends beyond the ring, as he mentors emerging talent and participates in cross-promotional events, solidifying his role as a bridge between wrestling’s storied past and its dynamic future.
Bailey Matthews (born December 30, 1996) is an English professional wrestler. He is signed to WWE, where he performs on the NXT brand under the ring name Charlie Dempsey. Wrestling fans around the globe have been captivated by his performances and are eager to learn more about his journey to the top.
Early Life and Background
Born in Atlanta, Georgia, during a time when his father, William Regal, was establishing himself as a force in American wrestling promotions, Charlie Dempsey-real name Bailey Matthews-grew up immersed in the world of suplexes, submissions, and storytelling in the squared circle. The family environment was one steeped in British wrestling traditions, despite the American birthplace, as Regal’s English heritage and catch-style expertise shaped young Bailey’s worldview. These early experiences profoundly influenced Dempsey’s identity, instilling a respect for technical wrestling that set him apart from peers drawn to more flashy styles.
From an early age, Charlie was exposed to the rigorous training and discipline required to succeed in wrestling. Charlie Dempsey’s father, William Regal, is a well-respected figure in the wrestling world. His legacy has had a profound impact on Charlie’s career, providing guidance and inspiration as he navigates the challenges of professional wrestling.
Early Career
Training under his father’s watchful eye from a young age, he honed skills in grappling and chain wrestling, drawing on Regal’s decades of experience in promotions like WCW and WWE. This foundation not only prepared him for a career in the ring but also fostered a deep appreciation for the sport’s history, pushing him to pursue excellence while navigating the expectations that come with being a second-generation star.
Read also: Steve Keirn: Wrestling Icon
Dempsey’s entry into professional wrestling came on February 9, 2018, debuting for All Star Wrestling under the name Joe Bailey, where he faced early defeats that built his resilience and refined his technique. February 17, 2018 - ASW: James Mason defeated Joe Bailey. Throughout 2019 and 2020, Bailey made appearances in All Star Wrestling (ASW), Progress Wrestling, Westside Xtreme Wrestling (wXw), and Evolve.
In 2020, Matthews joined New Japan Pro-Wrestling (NJPW) as a Young Lion. However, he would never end up appearing for the company, as he later left for WWE.
Charlie Dempsey made his professional debut in the wrestling world under his birth name, Bailey Matthews. However, he later adopted the ring name Charlie Dempsey to carve out his own identity in the sport.
WWE NXT Career
Bate vs. Dempsey – NXT Global Heritage Invitational Match: NXT Level Up highlights, Sept. 15, 2023
The pivotal moment arrived in January 2021 when Dempsey signed with WWE, where he was assigned to the NXT UK brand. In January 2021, Matthews signed with WWE, where he was assigned to the NXT UK brand. Matthews later reverted to the ring name Charlie Dempsey. Dempsey made his debut on 25 February edition of NXT UK, where he was defeated by Tyler Bate.
Dempsey made his debut for the NXT brand on the August 30, 2022 episode of NXT where he faced Andre Chase in a losing effort. His next appearance was on the September 9, 2022 episode of NXT Level Up where he faced Bodhi Hayward in a winning effort.
Read also: "Pretty Boy" Larry Sharpe's impact on wrestling
Dempsey later joined Teoman and Rohan Raja to form Die Familie and began a feud with Gallus, establishing himself as a heel in the process. On the 18 November edition of NXT UK, Die Familie defeated Gallus in their first ever match as a team. Die Familie also started a feud with A-Kid. On the 10 March 2022 edition of NXT UK, Dempsey defeated A-Kid. Dempsey was later challenged by A-Kid to a British Rounds Rules match. This took place on the 21 April edition of NXT UK, where Dempsey won 2-1 in the sixth round.
In August 2022, Dempsey moved to the NXT brand. On the 14 February 2023 edition of NXT, Dempsey started associating with Drew Gulak, where Gulak served as a teacher for Dempsey. February 14, 2023 - NXT: Charlie Dempsey defeated Hank Walker w Drew Gulak. On the 18 April 2023 edition of NXT, Dempsey challenged Wes Lee for the NXT North American Championship, which he lost. In the following months, Dempsey and Gulak formed No Quarter Catch Crew (NQCC), where they would later be joined by Myles Borne and Damon Kemp.
Throughout August and September, Dempsey competed in the NXT Global Heritage Invitational to crown a #1 Contender for the NXT Heritage Cup. Dempsey came up empty-handed as he lost to the likes of Axiom (formerly A-Kid), Tyler Bate, and Butch.
NXT Heritage Cup Championship
On the February 27, 2024 edition of NXT, Dempsey defeated The Meta-Four's Noam Dar 2-1 in a British Rounds Rules match to become the new NXT Heritage Cup Champion. On the May 14, 2024 episode of NXT he lost the championship to Tony D'Angelo. On the August 13, 2024 episode of NXT Dempsey defeated Tony D'Angelo to win the NXT Heritage Cup Championship for a second time.
At NXT: Roadblock, NQCC announced that the NXT Heritage Cup will be defended by the whole stable under the "Catch Clause". Under the Catch Clause, NQCC as a whole referred to themselves as the NXT Heritage Cup Champions but WWE only recognize Dempsey as the official champion. The Catch Clause was invoked on the 19 March episode of NXT, with Gulak defeating Chase University's Riley Osborne 2-1 to successfully defend the Cup.
Read also: The Story of Chris Melendez
On the 16 April episode of NXT, The D'Angelo Family leader Tony D'Angelo revealed that his Family were hired by NQCC to (kayfabe) eliminate Gulak. In reality, Gulak was written off following allegations from Ronda Rousey that Gulak grabbed her pants' drawstrings backstage in 2022. Gulak subsequently left WWE on 3 May. D'Angelo demanded payment for the job but NQCC refused, causing a brawl between the two factions and resulting in a six-man tag team match between the two factions at Week 1 of Spring Breakin', which was won by The D'Angelo Family (D'Angelo, Channing "Stacks" Lorenzo and Luca Crusifino).
On the 7 May episode of NXT, Dempsey and Borne faced Tyson DuPont and Tyrek Igwe in a tag team match. Before the match started, the match referee was declared "unavailable" and Stacks was announced as the special guest referee, costing Dempsey and Borne the match through a fast count. After the match, an irate Dempsey gave D'Angelo a title shot at the NXT Heritage Cup as payment due to the D'Angelo Family and invoked the Catch Clause, which was nullified when D'Angelo and his Family kidnapped Kemp and Borne later that night. One week later, D'Angelo defeated Dempsey 2-1 to win the Cup, ending Dempsey's reign at 76 days.
After the loss of the Cup, Dempsey declared that the stable needs structure and a chain of command and assumed a leadership role. On the 24 December episode of NXT, Lexis King, with Dempsey's father William Regal as his cornerman, faced Dempsey in a rematch for the NXT Heritage Cup. Regal passed his brass knuckles for King to use against Dempsey but King refused. Regal then punched King, to which the brass knuckles fell into the ring. The referee saw Dempsey pick up the brass knuckles and assumed that Dempsey used it on King and disqualified Dempsey. In British Round Rules, the Cup change hands upon disqualification of the reigning champion, resulting in King becoming the new NXT Heritage Cup Champion, ending Dempsey's second reign at 134 days. This is also the first instance of the NXT Heritage Cup changing hands due to disqualification.
However, due to a grey area in British Round Rules on whether the Cup changes hand upon disqualification of the reigning champion, NXT general manager Ava ordered King to return the Cup back to Dempsey and announced that they will compete for the Cup in a one-fall match at NXT: New Year's Evil on 7 January 2025, where he lost the Cup back to King.
Recent NXT Storylines
Following NXT Battleground, Dempsey and the rest of No Quarter Catch Crew effectively turned face due to the outpouring support for Myles Borne during his NXT Championship match against Oba Femi despite failing to win the title. On the 3 June episode of NXT, Borne defeated Dempsey "British Rounds Rules" match, thus leaving No Quarter Catch Crew.
On December 5, 2025 - TNA Final Resolution: Mike Santana defeated Charlie Dempsey. The NXT contingent then went on the attack and ended the show threatening to burn the logo on the ring mat, but TNA talent and officials stopped them before they could.
Other Notable Appearances
Dempsey made his return to Japan with All Japan Pro Wrestling (AJPW) on 31 December 2023, where he teamed up with Yuma Anzai to face Tatsumi Fujinami and his son LEONA in a winning effort. Dempsey made his Total Nonstop Action Wrestling (TNA) debut on the 4 July 2024 episode of TNA Impact! where he attacked Leon Slater and Trey Miguel during their match.
Wrestling Style and Persona
Charlie Dempsey is known for his technical prowess and adaptability in the ring. His style combines traditional wrestling techniques with modern maneuvers, making him a formidable opponent.
Throughout his career, Charlie Dempsey has been part of several memorable matches that have solidified his place in wrestling history:
- Match vs. JD Drake (2022): This match highlighted Charlie’s ability to adapt to different wrestling styles, as he faced off against the hard-hitting JD Drake.
- Match vs. Tyler Bate (2023): In a thrilling encounter, Charlie Dempsey took on Tyler Bate, delivering a performance that was both technically sound and emotionally charged.
Mentorship and Influence
Throughout his career, Charlie Dempsey has benefited from the mentorship of his father and other seasoned wrestlers. This support has been instrumental in his development, allowing him to learn from the best and refine his skills.
Future Prospects
As Charlie Dempsey continues to make waves in the wrestling world, fans and critics alike are eager to see what the future holds for him. With his unique blend of skill, charisma, and determination, Charlie is poised to achieve even greater success in the coming years. Given his impressive track record and growing popularity, many believe that Charlie Dempsey is a strong contender for championship titles in the near future.
Legacy
Charlie Dempsey is more than just a wrestler; he is a testament to the power of dedication and hard work. As he continues to rise through the ranks, Charlie’s influence on the wrestling world will undoubtedly grow, inspiring a new generation of wrestlers to follow in his footsteps. Whether you’re a longtime fan or new to the sport, Charlie Dempsey’s journey is one worth watching.
Match Statistics
| Date | Event | Opponents | Result |
|---|---|---|---|
| February 17, 2018 | ASW | vs. James Mason | Lost |
| February 14, 2023 | NXT | vs. Hank Walker | Won |
| April 28, 2023 | NXT Live Event | vs. Houston Miller | Won |
| February 10, 2024 | NXT Live Event | with Myles Borne & Damon Kemp vs. Kale Dixon | Won |
| June 1, 2024 | NXT Live Event | with Myles Borne & Damon Kemp vs. Cutler James & Dion Lennox | Won |