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In September 2019, DiMaggio pleaded guilty to charges by the FBI of Felony Wire Fraud in violation of 18 U.S.C. § 1343 and faces up to 20 years in a federal prison for stealing money from a charity for homeless children.

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.

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On August 5, 2016, the promoter wired $750,000.00 dollars to an account controlled by DiMaggio, who had withdrawn the money four days later.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.

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 show Oh Sit and TBS's Lopez Tonight, hosted by George Lopez.

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.

Robin DiMaggio (born 1971) is an American convicted felon and a former drummer/percussionist originally based out of Los Angeles, California, United States.