Trustee David Wadsworth alleges that after Tampa Bay Buccaneers’ safety Shilo Sanders filed for bankruptcy in October 2023, he transferred approximately $250,000 from his company, Big 21 LLC, into his personal accounts.
Aug 16, 2025; Pittsburgh, Pennsylvania, USA; Tampa Bay Buccaneers safety Shilo Sanders (28) watches a game against the Pittsburgh Steelers during the third quarter at Acrisure Stadium. Mandatory Credit: Barry Reeger-Imagn Images
Aug 16, 2025; Pittsburgh, Pennsylvania, USA; Tampa Bay Buccaneers safety Shilo Sanders (28) watches a game against the Pittsburgh Steelers during the third quarter at Acrisure Stadium. Mandatory Credit: Barry Reeger-Imagn Images
The complaint, filed against Sanders and his companies Big 21 LLC and Headache Gang LLC, alsoalleges violations of bankruptcy law for transferring funds that should have been part of the bankruptcy estate.
The complaint further claims that Headache Gang LLC received $202,500 from NIL contracts in December 2023, after the bankruptcy filing.
The trustee contends that these earnings were based on pre-bankruptcy NIL contracts and belong to the bankruptcy estate.
The trustee seeks to recover the $250,000 in unauthorized transfers, the $202,500 from the Headache Gang NIL contracts, and additional assets to distribute to creditors.
Read “Shilo Sanders Accused Of Making Unauthorized Bank Transfers” on SmartNews: https://t.co/Wa4oDMTBnC #SmartNews
— Gene Melius (@gene_melius2) October 25, 2025
Sanders’ attorney had previously stated he cooperated with the process and voluntarily turned over $210,000 to the trustee. However, the trustee believes more funds are due to the estate.
Sanders filed for bankruptcy to address an $11.89 million default judgment against him in a lawsuit filed by a former high school security guard named John Darjean. Darjean, fighting Sanders’ attempt to discharge the debt, is also a creditor in the bankruptcy case.
Shilo Sanders’ Bankruptcy Could Fail as Victim Claims “Willful and Malicious Injury”
Sanders was involved in a fight at Focus Learning Academy in Dallas, Texas, with school security guard Darjean in 2015. Darjeantried to take Sanders’ phone for breaking the school’s no-phone rule.
John Darjean, the security guard from 2015 incident with Shilo Sanders, breaks down the whole altercation😳
The Fight pic.twitter.com/GSTAVyXhcq
— Bolt Analysis (@BoltUpMedia) May 24, 2024
The security guard said Sanders hit him with an elbow and fists, causing permanent nerve damage and a serious neck injury. Sanders said he acted in self-defense.
Darjean sued Sanders and his parents for money in the following year. Sanders’ parents, Deion and Pilar Sanders, were dropped from the case, leaving Sanders as the only defendant.
The case moved slowly, and Sanders did not appear at trial in March 2022. The court gave a default judgment against Sanders for about $11.89 million.
Sanders filed for Chapter 7 bankruptcy to cancel the debt in 2023. Darjean is fighting the bankruptcy, saying the debt came from a “willful and malicious injury.” If Darjean wins, Sanders’ debt could remain, risking his future earnings, including any NFL salary.
Sanders faces legal challenges in his bankruptcy case, including investigations into bank transfers and NIL earnings and a $11.89 million debt dispute with Darjean. The outcome will depend on whether his actions were deemed “willful and malicious,” potentially impacting his future finances.