type: timeline_event The Department of Justice settled a civil lawsuit against Roger Stone and his Drake Ventures LLC shell company for $2.1 million in July 2022, resolving allegations that Stone had fraudulently transferred assets to avoid paying nearly $2 million in federal taxes. Drake Ventures was a Delaware-registered LLC that federal investigators characterized as Stone's "alter ego"—a company with no legitimate business operations, no independent website, and no independent phone number, yet one through which Stone channeled hundreds of thousands of dollars in personal expenses including groceries, dental bills, and personal services.
Prosecutors documented that Drake Ventures had received payments from Stone's political and media activities before distributing funds for his personal benefit, creating a paper trail of fraudulent transfers designed to shield assets from IRS collection. When the IRS moved to collect Stone's tax debt, prosecutors alleged he transferred a Fort Lauderdale property to the Bertran Family Revocable Trust for $400,000—a transaction the government characterized as a fraudulent transfer to evade collection. The settlement required Stone to pay $2.1 million without admitting wrongdoing, resolving the civil enforcement action.
The Drake Ventures case emerged as Stone was simultaneously navigating the aftermath of his 2019 federal conviction for witness tampering, obstruction, and lying to Congress—a conviction that President Trump commuted in 2020 and fully pardoned in late 2020. The shell company arrangement demonstrated Stone's comfort with sophisticated financial structures to conceal assets and evade oversight, skills developed over decades as a political operative. The settlement illustrated how presidential pardons for criminal convictions do not eliminate civil tax liability, and that Stone's financial entanglements with federal authorities extended beyond his better-known political crimes.