This Florida Drug Smuggler Escaped 7 Life Sentences—Twice

Dickie Lynn’s story shows how the drug war warped the Criminal Justice System.

- By C. J. Ciaramella

For a long time, Richard “Dickie” Lynn didn’t think he’d ever see the mesmerizing blue waters of the Florida Keys again.

The former drug smuggler and onetime escapee from federal prison had received seven life sentences after he was convicted as part of a massive 1989 drug trafficking sting. He was released last June after serv­ ing 31 years.

I caught up with Lynn, 66, a few months after his release. Today, he sports a mop of light brown hair and a graying goa­ tee. He’s back in his element, wearing the typical Keys uniform: performance fishing shirt, shorts, and flip­flops.

I wanted to talk to him not only because his story is a wild true-crime tale involving Cuban dissidents, former U.S. Attorney General Jeff Sessions, and corrupt Customs agents. I wanted to talk to him because the prosecution, incarceration, and improbable release of Dickie Lynn shows how the drug war warped the criminal justice system, and how the country has slowly tried to fix it.

From the harsh sentences of the 1980s to the criminal jus­ tice reform movement of the 2010s, Lynn experienced it all. His life story is also the tale of four decades of the U.S. criminal justice system—its failures and flaws, and its recent turn toward redemption.

FLORIDA MAN HAS FAST BOAT, DRUG

Smuggling business Lynn grew up