On the October 5, 2021 episode of NXT, D'Angelo made his WWE debut with the heel gimmick of an Italian-American mobster, defeating Malik Blade in only a few minutes. On December 5, at NXT WarGames, D'Angelo, Bron Breakker, Carmelo Hayes and Grayson Waller defeated Team Black & Gold (Johnny Gargano, LA Knight, Pete Dunne and Tommaso Ciampa) in a WarGames match.
After a series of victories against Ru Feng, Dexter Lumis and Andre Chase, D'Angelo suffered his first loss against Dunne on the December 21 episode of NXT 2.0, brutally attacking Dunne himself with a crowbar after the loss. As a result, D'Angelo defeated Dunne in a Crowbar on a Pole match on the January 11, 2022 episode of NXT 2.0. On the January 25 episode of NXT 2.0, D'Angelo lost to Cameron Grimes due to interference from Dunne, failing to challenge him for the NXT North American Championship. On February 15, at NXT Vengeance Day, D'Angelo lost to Dunne in a weaponized steel cage match. On April 2, at NXT Stand and Deliver, D'Angelo defeated Tommaso Ciampa in Ciampa's last match on the NXT brand. On June 4, at NXT In Your House, D'Angelo and his newfound henchmen Channing "Stacks" Lorenzo and Troy "Two Dimes" Donovan defeated Legado del Fantasma and, as per the stipulation, LdF had to join the D'Angelo Family. On the June 21 episode of NXT 2.0, D'Angelo was defeated by Carmelo Hayes, missing out on an opportunity to capture the NXT North American Championship due to Santos Escobar interfering. On the August 2 episode of NXT 2.0, D'Angelo and Lorenzo faced The Creed Brothers for the NXT Tag Team Championships, but were defeated due to Escobar's interference. On August 16, at NXT Heatwave, D'Angelo defeated Escobar in a street fight and, as per the stipulation, Legado del Fantasma had to remain linked to the D'Angelo Family, while Escobar had to leave NXT.
On the September 27 episode of NXT, D'Angelo faced Wes Lee to qualify for a ladder match for the vacant NXT North American Championship at NXT Halloween Havoc, but was defeated via referee decision. On the December 27 episode of NXT, D'Angelo faced Lee for the NXT North American Championship but, due to interference from Dijak, lost the match. On January 10, 2023, at NXT New Year's Evil, D'Angelo lost to Dijak. At NXT Roadblock on March 7, D'Angelo defeated Dijak in a "Jailhouse street fight". At NXT Stand and Deliver, D'Angelo and Stacks failed to win the NXT Tag Team Championships in a triple threat match. The D'Angelo Family had a brief feud with Pretty Deadly, where they lost to them on the April 4 episode of NXT but defeated them three weeks later at NXT Spring Breakin' in a trunk match. At The Great American Bash, D'Angelo and Channing "Stacks" Lorenzo defeated Gallus to win the NXT Tag Team Championships. At NXT Halloween Havoc, D'Angelo and Stacks lost the titles to Chase University (Andre Chase and Duke Hudson), but would defeat Chase and Hudson on the November 14 edition of NXT to become two-time NXT Tag Team Champions. On the February 13, 2024 episode of NXT, D'Angelo and Stacks lost the titles to the 2024 men's Dusty Rhodes Tag Team Classic winners Bron Breakker and Baron Corbin, ending their second reign at 91 days.
On the February 27 episode of NXT, D'Angelo interrupted the contract signing between Carmelo Hayes and NXT Champion Ilja Dragunov. NXT General Manager Ava would then set a match between Hayes and D'Angelo for NXT Roadblock to determine the number one contender to face Dragunov for the NXT Championship at NXT Stand and Deliver. At Roadblock, D'Angelo introduced Luca Crusifino as the "consigliere" of The D'Angelo Family and went on to defeat Hayes after using Trick Williams' entrance music to distract Hayes. At Stand and Deliver on April 6, D'Angelo failed to defeat Dragunov for the title. On the April 16 episode of NXT, D'Angelo revealed that his Family were hired by No Quarter Catch Crew (Charlie Dempsey, Damon Kemp and Myles Borne) to eliminate their leader Drew Gulak. 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 Spring Breakin' on April 23, which was won by The D'Angelo Family. On the May 7 episode of NXT, Dempsey and Borne faced Tyson DuPont and Tyriek Igwe. 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. On the following episode of NXT, D'Angelo defeated Dempsey 2–1 in British Rounds Rules to win the Cup, his first singles championship in WWE. D'Angelo lost the Cup back to Dempsey on the August 13 episode of NXT after outside interference from NQCC's new stablemate Wren Sinclair, ending his reign at 90 days. On September 1 at NXT No Mercy, D'Angelo failed to win the NXT North American Championship from Oba Femi. However, the following month, D'Angelo defeated Femi in a rematch on the October 8 episode of NXT to win the title, ending Femi's record-setting title reign at 273 days and becoming the first wrestler to win the NXT Tag Team, Heritage Cup and North American Championships. At Halloween Havoc on October 27, D'Angelo defeated Femi in a rematch to retain the title in a Tables, Ladders and Scares match.