In 2017, a Florida man named Gerald Tobin alleged Avenatti failed to pay him $28,700 for private investigatory work. As a result, Avenatti's firm was abruptly forced into bankruptcy.[46] In various news reports, including work done by CNN, Tobin was found to be an ex-con with four decades of convictions and jail time and not a licensed investigator. Tobin's claim forced Avenatti into bankruptcy which caused Avenatti to cancel a deposition in an unrelated lawsuit days later, raising the question of collusion between Avenatti and Tobin. The issue was resolved when the pair entered into a Non-Disclosure Agreement, and Avenatti paid Tobin the $28,700.[46]
In 2018, Avenatti's law firm was subjected to a $10 million judgment in U.S. bankruptcy court.[47] Avenatti has also defaulted on a $440,000 judgment in back taxes, penalties, and interest that he was personally obligated to pay under another bankruptcy settlement. The U.S. Attorney's office asserted in court that a motion seeking payment would soon be filed against Avenatti.[47] Eagan Avenatti had been in Chapter 11 bankruptcy proceedings and, in December 2017, had agreed to pay $4.8 million in unpaid fees to a former partner, $2 million in back taxes, and $1 million to other creditors.[48] In June 2018, the former partner filed a motion in U.S. bankruptcy court asking for a lien on any and all legal fees Avenatti's firm might collect, up to $10 million, from clients in 54 cases including his representation of Stormy Daniels.[49]
Avenatti has on several occasions, including in a post to Twitter, expressed interest in running for president in 2020.[50] In a CBC TV interview published in September 2018, Avenatti said he would run in 2020 only against Trump or Pence.