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In January 1973, the DEA arrested Matthews at McCarran International Airport in Las Vegas, ahead of a planned trip to Los Angeles with his girlfriend Cheryl Denise Brown, on charges of tax evasion and conspiracy to distribute heroin and cocaine. A federal magistrate originally set bail at $5 million, the highest bail amount ever set at the time. The bail was reduced to $2.5 million when Matthews agreed to not fight extradition and be returned to New York. After a few weeks in detention in New York, his bail was further reduced to $325,000. He was indicted on six counts of tax evasion and conspiracy to distribute heroin and cocaine and faced 50 years in prison. On July 2, 1973, Matthews was scheduled to appear in a Brooklyn courthouse but never showed. He allegedly took $20 million and fled the country with Brown. Matthews left behind his common-law wife, their three sons, and their Staten Island mansion and was never seen again. The Federal Bureau of Investigation (FBI) placed a $20,000 bounty on Matthews, the highest set by a federal agency since the FBI placed the same amount for the capture of bank robber John Dillinger.