As a drummer and percussionist, DiMaggio performed and recorded with many diverse artists. On September 9, 2013, DiMaggio took the role of Musical Director and drummer for the late night TV show the Arsenio Hall Show on CBS. Prior to Arsenio, he was briefly the house band drummer on the CW's game showOh Sit and TBS's Lopez Tonight, hosted by George Lopez.
Embezzlement conviction
According to court documents, in May 2016, DiMaggio was originally contacted by a nonprofit org registered in Bulgaria to recreate a "Live Aid" style charity concert in the Bulgarian capital of Sofia to raise money for the homeless and displaced children of the wars in conflict zones worldwide. DiMaggio offered to contract and obtain talent for the event that was set for October 2016. Not long before the event was scheduled to take place, many in the Bulgaria foundation had doubts about the promised "galaxy of stars" including Mick Jagger to Sofia for a big charity concert – but people suspected early on that it was all just a big hoax. On August 5, 2016, the promoter wired $750,000.00 dollars to an account controlled by DiMaggio, who had withdrawn the money four days later. DiMaggio during a press conference said he had received "verbal confirmations" concerning participation from Johnny Depp, Mick Jagger, Bruno Mars, Justin Timberlake, Rod Stewart, the band Earth, Wind and Fire, and others. Court records show that DiMaggio took the money, provided to him to escrow to secure the talent and used it as his own. Buying his ex wife a 275k home, an additional two cars and paying credit card debt. DiMaggio used the money to support his lifestyle and purchase a home for his wife. More money was spent on a Volvo as well as another purchase of an auto for $24,000.00. Over $15,000.00 in credit card payments as well as $53,821.91 in debit card and cash totaling over $37k. Prior to his arrest and upon receiving a request from his victim for a refund, DiMaggio told the foundation the money had been delivered to musicians and bankruptcy court records show in fact he had simply used the money as his own. Once confronted he told the victims that he was "Moving to Paris" his birthplace, presumably to avoid criminal prosecution. DiMaggio on September 25, 2019, was criminally convicted with his guilty plea to the charges that he embezzled over $750,000.00 from a charity for homeless children, a Bulgarian-based non-profit. The "Peace for You Peace for Me Foundation". On September 25, 2019, DiMaggio pleaded guilty to the charges and will be sentenced April 15, 2020, he is now facing a 20 year federal prison sentence. The case had previously heard in civil bankruptcy court where he had admitted he bought his ex-wife's home with the money. The 'Peace for You Peace for Me Foundation' was awarded a $1.2 million award in Mr. DiMaggio's bankruptcy court case.
Prison sentence
DiMaggio faces incarceration for up to 20 years, in a US U.S. Federal Prison in exchange for his guilty plea for stealing money from homeless children. No comments were made in the plea agreement pertaining to the exposure of potential prison violence due in part to the nature of his crimes upon homeless and displaced children. As a Federal Inmate, he will be required to serve his time in a US Federal prison. The Federal prison system has no parole. Under the Sentencing Reform Act of 1984, Congress eliminated parole for federal defendants convicted of crimes committed after November 1, 1987. The Sentencing Reform Act also requires DiMaggio is to serve a minimum of 85 percent of his sentences behind bars before becoming eligible for release.