Barry Seal was a real-life American anti-hero. The kind who gets HBO to do a movie based on his life after his death. On Feb. 19, 1986, at around 6 p.m., the burly pilot pulled his white Cadillac into the Salvation Army halfway house in Baton Rouge, La. He had been staying there as part of a plea bargain stemming from his conviction for marijuana smuggling. As Seal parked the Caddy, a man carrying a MAC-10 machine gun approached the driver’s side. The assassin unleashed two quick bursts, emptying the magazine into Seal’s body, neck, and head. Seal died instantly, but his legend lives on.
Here is a timeline of Seal’s greatest exploits:
1958 – As a 19-year-old pilot, Seal flew weapons to Fidel Castro when the Cuban strongman was leading the revolution against Fulgencio Batista.
1964 – Seal landed a job as a pilot for TWA Airlines, becoming the company’s youngest 707 captain and later its youngest 747 captain.
1972 – TWA fires Seal following his arrest in New Orleans on charges of flying explosives to anti-Castro Cubans in Mexico. The buyer turned out to be an undercover federal agent.
1979 – Three years into his new career as a drug smuggler, Seal gets arrested in Honduras with 40 kilos of cocaine worth a reported $25 million. While in prison, he met William Roger Reaves, a doper who worked for the Ochoa family and Pablo Escobar, leaders of the Medellin Cartel in Colombia.
1982 – Seal officially joined the Medellin Cartel, which at the time formed a 2,000 man army to vanquish M-19, a Marxist revolutionary group that was messing with the Colombian drug barons. Seal moved tons of yeyo into the United States and established his base in Mena, Arkansas.
1984 – Seal gets indicted in Ft. Lauderdale for smuggling Quaaludes and money laundering. After failing to convince federal prosecutors to use him as a snitch to shave off time from his possible prison sentence, Seal goes over their heads and cuts a deal with then-Vice President George Bush’s Task Force On Drugs.
Using his C-123 transport plane, which he dubbed The Fat Lady, Seal undertook an undercover DEA mission to catch the Medellin Cartel bosses and members of the Marxist Sandinistas in Nicaragua engaging in narcotrafficking. He equipped The Fat Lady with a hidden camera that photographed Escobar helping Nicaraguan soldiers load 1,200 kilos at the airport in the capitol city of Managua.
As a result of Seal’s cooperation, the judge in his Florida case praised Seal and reduced his sentence to six months probation.
December 1984 – Seal gets busted in Louisiana for flying in a cargo of marijuana.
October 1985 – Seal testifies against the Chief Minister of the Turks and Caicos Islands, Norman Saunders, and members of the Medellín Cartel. Seal also testified before the President’s Commission on Organized Crime.
December 1985 – U.S. District Court Judge Frank Polozola sentences Seal to six months supervised probation, ordering him to report to the half-way house from 6 p.m. to 6 a.m. every day. The judge also barred Seal from carrying a gun or hiring armed bodyguards, which his lawyer argued amounted to a death sentence for Barry. Seal told friends that the judge “made me a clay pigeon.”
March 1986 – Two weeks after Seal’s murder, Louisiana Attorney General William Guste hand-delivered a five-page letter to U.S. Attorney General Edwin Meese, formally requesting a complete investigation with respect to the government’s relationship with and handling of Seal.
October 1986 – A Sandinista patrol shoots down The Fat Lady, which was being used by the CIA to supply the anti-Sandinista forces known as the Contras.
March 1987 – A Baton Rouge state grand jury indicted Miguel Velez, Bemardo Antonio Vasquez, Luis Quintero, and Jose Renteria-Campo for Seal’s murder.Two months later, a jury found the three men guilty of first-degree murder and sentenced all three to life in prison without parole. Renteria-Campo was extradited to Miami to be tried on federal weapons charges.
Prosecutors claimed the trio were contracted by the Medellin Cartel, who wanted Seal dead because he was set to testify against cartel co-leader Jorge Ochoa, who was hiding out in Spain. As a result of Seal’s death, the U.S. government was unable to extradite Ochoa on narcotrafficking charges.
1991 – HBO premieres “Double Crossed,” a made for cable TV movie based on Seal’s life and starring Dennis Hopper as the lead.