Roger Clinton's trouble with the law in the 1980s did not deter him from future nefariousness. As it turned out, he apparently only got more involved in the criminal underworld that keeps the illicit drug trade running. In 2001, The New York Times reported on a golf game in 1999 in which Roger Clinton was given a Rolex watch by a man who interrupted his golf game on the 10th hole. The man turned out to be Tommy Gambino, as in the notorious Gambino crime family of the Sicilian Mafia. The two had a muted conversation, and when Tommy left, Roger told his golf partners that he was "helping" Tommy's father Rosario, who was serving a 45-year sentence for trafficking heroin. The Gambino family also cut Roger a check for $50,000.
What Roger didn't know at the time was that his golf buddies that day were actually intelligence officers from the Air Force. Roger had pretty much just told them that he'd been paid to influence his brother to give an incarcerated gangster a presidential pardon. But the president wasn't convinced by his little brother's shiny new watch. Controversial as Bill Clinton's last-day pardons were, they did not include any for the Gambino family.