Known as "The Kentucky Gentleman" and "Sexy Chuckie T", he was a member of the Best Friends stable alongside original tag team partner Trent Beretta, Orange Cassidy, Kris Statlander, and Danhausen.

The most prominent of these was the then-newly restarted Chaos Pro Wrestling (CPW) in Brookport, Illinois, where he began his friendship with fellow wrestler Trevor Mann, who has since been known by the ring name Ricochet.

[15] However, Taylor would quickly become a villain during his match with Eddie Kingston at the Brick event on November 17, gaining an upset victory with some help from an interfering "Sweet & Sour" Larry Sweeney.

ended their losing streak by defeating Da Soul Touchaz (Acid Jaz, Marshe Rockett and Willie Richardson) and 3.0 (Scott Parker and Shane Matthews) and Soldier Ant in six man tag team matches on September 18 and 19.

defeated Team Osaka Pro (Atsushi Kotoge, Daisuke Harada and Ultimate Spider Jr.), avenging their loss from the previous year and advancing to the semifinals of the tournament.

[40][51] On September 18, Taylor and Gargano defeated Jigsaw and Mike Quackenbush to win the Chikara Campeonatos de Parejas for the first time.

[52] Taylor and Gargano made their first title defense on October 7, defeating Momo no Seishun Tag (Atsushi Kotoge and Daisuke Harada) with help from Icarus in the third match between F.I.S.T.

[52] On October 30, Taylor and Icarus, who replaced Gargano who was unable to attend the event due to traveling issues, successfully defended the Campeonatos de Parejas against the Throwbacks (Dasher Hatfield and Sugar Dunkerton).

[53] On August 2, Chikara's Director of Fun, Wink Vavasseur, named Sugar Dunkerton, who had announced his wish to join a stable, the fourth member of F.I.S.T.

[55][56] On September 14, F.I.S.T., represented by Taylor, Icarus and Gargano, entered the 2012 King of Trios tournament, defeating Team Osaka Pro (Ebessan, Kikutaro and Takoyakida) in their first round match.

On August 30, 2008, Taylor made his Pro Wrestling Guerrilla debut at All Star Weekend 7, defeating female wrestler Candice LeRae in a specialty match.

[64] The next night, he teamed with fellow Chikara mainstay Vin Gerard to take on The Dynasty (Scott Lost and Joey Ryan) in a losing effort.

In the quarterfinals, they overcame the team of Dark & Lovely (Scorpio Sky and Human Tornado), who were substituting for scheduled opponents Los Luchas.

Becoming a sensation with fans overnight, they next faced World Tag Team Champions The Young Bucks in a title match, losing in controversial fashion.

[70] Now referred to as "Men of Low Moral Fiber", Taylor and Omega were scheduled to face Danielson and Roderick Strong (Hybrid Dolphins) in June, but a staph infection kept the former out of action.

[74] With Omega winning the World Championship at the 2009 Battle of Los Angeles, Taylor and new tag team partner Tornado (having parted ways with Generico after a brief reunion), known collectively as the "2 Skinny Black Guys of Low Moral Fiber", were scheduled to take on the Bucks for the Tag Team championship on January 30, 2010, at WrestleReunion 4, however, due to a snowstorm Taylor was forced to miss the event.

[81] In the finals the Best Friends defeated the Inner City Machine Guns (Rich Swann and Ricochet) to win the 2014 Dynamite Duumvirate Tag Team Title Tournament.

In December 2016 at "Mystery Vortex IV", the still-unbeaten Taylor earned his first shot at the PWG Championship by defeating Adam Cole in a #1 Contender's match.

On January 16, 2010, Taylor participated in Evolve's first show, defeating Cheech in a qualifying match to earn a spot in the promotion's roster.

[98] At the following event on September 25, Taylor won another four-way match, this time defeating Drake Younger, Johnny Gargano and Rich Swann.

[100] On October 29 at Dragon Gate USA's first live pay-per-view, Bushido: Code of the Warrior, Taylor defeated Arik Cannon, Johnny Gargano and Ricochet in a four-way match.

[101] At the following day's tapings of Freedom Fight 2010, Ronin defeated Austin Aries, Genki Horiguchi and Ricochet in a six-man tag team match.

[107] On September 10 at Untouchable 2011, Taylor defeated Masato Yoshino, Naruki Doi and Sami Callihan to earn a match of his choosing for Ronin.

[110] The following day at Freedom Fight 2011, Taylor handed the belt to new champion, Ronin stablemate Johnny Gargano, seemingly putting their past differences aside.

[119] On May 14, 2017, Howard, billed as Chuckie T.,[5] made his debut for Ring of Honor (ROH) as Roppongi Vice's surprise partner in a six-man tag team match against Bullet Club.

[130] However, at All Out on August 31, Best Friends were defeated by The Dark Order's Evil Uno and Stu Grayson in a match where the winners qualified for the first round bye.

[131] Despite not receiving the bye, Best Friends still competed in the AEW World Tag Team Championship tournament, where they were eliminated in the first round by SoCal Uncensored.

[133] After winning a title shot when they defeated Private Party at Double or Nothing Buy-In,[134] they faced Kenny Omega and "Hangman" Adam Page at Fyter Fest night 1, which they lost.

In July 2023, Best Friends would begin feuding with the BCC, which led to the second ever Parking Lot Brawl, where Claudio Castagnoli and Jon Moxley were victorious with help from Wheeler Yuta, despite Orange Cassidy coming to help even the odds.

Best Friends would then align with The Lucha Bros and Eddie Kingston and at All In, they defeated the team of the BCC and Santana & Ortiz in a Stadium Stampede match.