Crimes, Cons and Capers: Custody Escapes

LeeAnn Huntoon

LeeAnn Huntoon

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LeeAnn Huntoon

From high fliers to repeat runners, how does law enforcement handle the most shocking and daring escapes? Find out on this episode of “Crimes, Cons and Capers: Custody Escapes.”

Watch the full episode of “Crimes, Cons and Capers: Custody Escapes on the Very Local app.

The Alcatraz Letter

Three convicts in San Francisco, California accomplished a feat that many before them have tried and failed: escaping Alcatraz. This mystery has puzzled historians and the public for more than half a century. In June 1962, brothers John and Clarence Anglin and Frank Morris managed to escape from “The Rock,” one of the country’s most secure prisons for decades and where the worst of the worst are imprisoned. A letter surfaced four decades later, allegedly from John Anglin, that states all three made it to shore that cold night and survived. Is it possible they could be living among us undetected?         


It’s a classic meetup – girl meets boy, girl falls in love, girl rents a helicopter and attempts to break boy out of prison. I’m sorry, come again? That’s exactly what happened in the mid-1980s when Joyce Bailey Maddox met Jesse Glenn Smith when she visited the jail with her church group. She rented a helicopter, pulled a gun on the pilot and ordered him to fly and land in the prison recreation compound where three inmates climbed inside and took off. They were found a week later after telling the owner of a car that they had stolen all about their brazen caper. 

Jailhouse, Rocked

Inmates have previously escaped from the Lincoln County jail in Chandler, Oklahoma, but these three particular inmates can be counted once since they escaped twice. In March 2017, these three were licking their wounds from a previous escape. One got through the ducts, into the kitchen looking for a snack, which turned into all three figuring out how to open a door and make a run for it. Of course they were caught but three months later they tried the same thing again and it worked again but this time it was four of them. Apparently this jail doesn’t have the facility to contain these prisoners. After a few days all four were caught. Third time’s the charm, right?

Gotta Jet!

On Nov. 9, 2021, a private company is transporting an inmate in Milwaukee, Wisconsin through the airport, the career criminal is being moved from Texas to Wisconsin and it’s at the airport where he somehow escaped custody. After disembarking, he asked to use the bathroom and once the escort unhooked the left cuff, he punched him and it was off to the races. Although he still had one handcuffed to a restraint belt he still ran past waiting cars into the parking garage where it was easy for him to blend in and make it out undetected. Days turned into weeks with still no sighting and during that time major changes were conducted with different agencies for better communication and rule changes with future transports. After nearly a year on the run, the inmate was taken into custody in Ohio.

Remember to Lock Up

On Jan. 3, 2022, in Effingham County, Georgia, a murder suspect is caught on film escaping from the prison. So how did he manage to escape? By walking out the door of course. Bad weather caused the computers and systems to go out and when it was restored that particular inmate’s door didn’t get locked back. To add insult to injury it took staff eleven hours to realize that he was missing and another nine hours to tell police that an inmate was on the loose. After three days his freedom comes to an end after being caught in a hotel room.  

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Watch every episode of Crimes, Cons and Capers streaming exclusively on the Very Local app. Interested in more True Crime content? Watch Season 1 and 2 of the Very Local Original Series, “Hometown Tragedy.”

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