The Cautionary
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Go to prison and learn new skills

Go to prison and learn new skills

And start a relationship with a drug cartel

George Pillari
January 15, 2026

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The purpose of the prison system is to take the bad guys off the street and discourage other bad guys from doing bad things. But prisons also perform a rehabilitation function so that once released, prisoners understand society better, have new skills, and have a chance at assimilating into a community rather than going back to a life of crime.

Ryan Wedding was a snowboarding prodigy from age 15, when he won the first race he entered. As he grew into his sculpted 6’3” frame, he made the Canadian national team and competed in the Salt Lake City Olympics in 2002.

Ryan Wedding

After the Olympics, Wedding became a marijuana grower and seller before graduating to cocaine, getting busted, and being sentenced to three years in prison.

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It was in prison that Wedding certainly made new friends and learned new skills that would help him once released.

He became close with one of his new friends, Jonathan Garcia, and the two were in regular contact once they were on the outside. As for skills learned, Wedding quickly became one of the largest drug smugglers in the world.

With Garcia at his side, Wedding rose through the ranks of the Mexico-based Sinaloa Cartel, one of the biggest and most violent drug-trafficking operations in existence.

El Chapo, former head of the Sinaloa Cartel

Wedding has been accused of moving more than a billion dollars of cocaine per year into the US. Inside of Sinaloa, he became known as El Jefe (“The Boss”).

To round things out, Wedding made the FBI’s Ten Most Wanted List as the kingpin cof Operation Giant Slalom. (Go here for the Department of Justice news release on the matter, it’s worth the click.)

The kid who became an Olympian, then a small-time pot dealer, was now one of the most dangerous drug lords in the world.

As the FBI started to penetrate Sinaloa, it flipped Wedding’s prison buddy Garcia and turned him into an informant. It did not work out well for Garcia. Wedding hired a sicario and Garcia was assassinated while having lunch at an outdoor cafe in Colombia, South America.

When Wedding received pictures of the confirmed kill, he gleefully sent them around and let people know he had “killed the rat.”

In an odd twist to the murder, Wedding was advised by a cartel attorney that if Garcia were to be eliminated, much of the FBI’s case against him would collapse. I guess he was just following the advice of counsel, right?

Wedding and his billion-dollar a year enterprise remain at large.

Key Takeaways

Illegal drug smuggling into the US is 20 times as large as illegal gambling.
We hold our athletes to ridiculous standards. Most last a few years in the bright lights then move on. It is not surprising that we continue to read about former athletes involved in drugs and gambling. What else are they to do?
Over the past dozen years, estimates indicate more than 200,000 killed as part of cartel-related violence. Drug lords are worse than depicted on television and in movies.

Things I think about

Your stomach acid is strong enough to dissolve razor blades, though you should never test this.