Deppen is known for his tenure with Chikara, promotion for which he made his first appearance at CHIKARA National Pro Wrestling Day 2018 from February 17, where he unsuccessfully challenged The Whisper for the Chikara Young Lions Cup.[5] He continued to wrestle for Chikara as part of the FIST stable, having Travis Huckabee as a tag team partner, both competing on house shows such as the CHIKARA Chikarasaurus Rex: A Deadly Secret from August 11, 2018, where they defeated The Colony (Green Ant and Thief Ant), The Creatures Of The Deep (Cajun Crawdad and Hermit Crab), and Xyberhawx2000 (Nytehawk and Razerhawk).[6] Other notable appearances made by Deppen are at the King of Trios tournament of the promotion. At the 2018 edition of the event, he teamed up with fellow FIST stablemates Icarus and Travis Huckabee, defeating Galactic Wildlife Commission (ThunderFrog, Air Wolf, and Wildcat) in the first-round match, but later fell short to The ResistANTce (Fire Ant, Green Ant [II], and Thief Ant) in the quarter-finals.[7] One year later at the 2019 edition of the event, he teamed up again with Icarus and Huckabee and defeated The Embassy (Prince Nana, Jimmy Rave, and Sal Rinauro) in the first-round, The Carnies (Nick Iggy, Kerry Awful, and Tripp Cassidy) in the quarter-finals, but stopped in the semi-finals where thet got defeated by The Nations (Mick Moretti, Jack Bonza, and Adam Hoffman).[8] At CHIKARA Fright Knight on April 27, 2019, Deppen teamed up with Travis Huckabee and defeated Princess KimberLee and The Whisper to win the Chikara Campeonatos de Parejas.[9]
Deppen made his debut in Ring Of Honor at ROH Wrestling #472 from October 2, 2020, in a ROH Pure Championship tournament first-round match in which he fell short to P. J. Black.[18] He continued to make sporadic appearances for the promotion, such as at ROH Wrestling #476 where he competed in a three-way dark match against Dak Draper and Wheeler Yuta.[19] At Final Battle 2020 from December 10, he defeated LSG, Josh Woods and Dak Draper in a four-way match to earn a shot at the ROH World Television Championship. Later that night, he unsuccessfully challenged Dragon Lee for the title.[20] On March 12, 2021, at ROH Wrestling #495, Deppen pulled out an upset victory against Kenny King.[21] At ROH Wrestling #502, a show which aired on May 1, 2021, Deppen defeated Tracy Williams to win the ROH World Television Championship, although the exact date the match took place is unknown due to ROH holding closed door tapings at the UMBC Event Center since August 2020, after resuming operations following a five-month hiatus due to the COVID-19 pandemic.[22]