Don Whittington and his two brothers were the only sibling trio of drivers to have ever qualified for the same Indianapolis 500 race. That was 1982.
During those heady years of racing, two of the Whittington brothers—along with two other famous Indy 500 drivers, Randy Lanier and John Paul Sr.—apparently also loved speed boats, barges and small planes… especially the ones full of weed from Colombia, Mexico and other such places.
In 1986, the four Indy 500 racers were all busted in connection with multi-million dollar schemes that funded, or partially funded, high-end racing teams.
Randy Lanier, convicted of moving hundreds of thousands of pounds of marijuana, ended up spending nearly three decades in prison, having been convicted as one of the country’s biggest weed kingpins.
The Whittington brothers were convicted within months of each other for trafficking marijuana. And John Paul Sr. went down shortly after.
During the 1980s, when the four men were on top of their racing game, many noticed that they had very little sponsorship and rarely gave interviews.
Then, as now, race cars are billboards on wheels, and drivers are media stars and corporate pitchmen. It’s common for them to have Hollywood publicists.
“There was talk within the racing ranks” about the Whittingtons and Lanier, said veteran racing broadcaster Paul Page per the Indy Star, “because the report was, they were actually buying race cars with cash.”
A new race car at that time cost about $1 million, which is usually paid by corporate sponsors—as long as they’re not weed companies. Recently NASCAR driver Carl Long was forced to strip the logo of a Colorado-based vaping company from his car.
Paying for big items in cash? Always a dead giveaway.
“A guy can show up in Gasoline Alley with $45,000 in cash in an attaché case wanting to buy a motor,” said auto racing journalist Robin Miller, who at the time wrote for the IndyStar. “But you didn’t know they were drug dealers. There was an assumption, but nobody ever could prove it. Nobody in racing ever brought it up.”
But apparently the DEA had noticed.
In March of 1986, Don and Bill Whittington pleaded guilty in connection with a multi-ton, multimillion dollar, Colombia-to-South Florida marijuana smuggling ring. Bill admitted to heading the organization, and his brother Don invested the profits in legitimate businesses, like race cars.
Later that year, Randy Lanier—who was the 1986 Indy 500 Rookie of the Year—was busted and found guilty of heading a different weed smuggling ring, which had imported 600,000 pounds of marijuana into the U.S. from South America.
Several months later, the fourth Indy-car driver, John Paul Sr., pleaded guilty to a marijuana-related racketeering charge, unrelated to either the Whittington or Lanier schemes.
The racing industry freaked out about its image, but eventually got over it.
Today, the four drivers are all free men. But the Whittington brothers seem to be back at it again—maybe.
In November 2014, the Miami DEA office filed a damning search warrant application accusing the brothers of a 10-year involvement in an international ring that sells planes to drug smugglers in Mexico, Venezuela, Colombia and Congo.
The Whittingtons’ multi-million dollar operation, Florida-based World Jet, Inc., has also been suspected of being involved in running CIA missions to Guantanamo Bay.
According to the Miami New Times, the DEA affidavit targeting the Whittington brothers claimed their company brokered the sale of a Gulfstream II corporate jet to a Florida duo—Clyde O’Connor and Gregory Smith—and was being used for “Operation Mayan Jaguar,” a clandestine program run by U.S. Immigration and Customs Enforcement.
One of their pilots is a “target for trafficking cocaine from South America to Central America,” according to the DEA affidavit.
Stranger still, the investigative website Narco News alleges that Smith, who today works as a pilot for the Whittingtons, has worked for numerous U.S. intelligence operations.
Such intrigue is the stuff of movies, or at least Miami Vice.
But then, so is our current government. As always, fact is stranger than fiction.