Written by: Jason Caines

Skateboarding often takes you to places where you're not allowed to go, and in many cities around the world it remains illegal. Over the years there have been a number of pro skaters who have have found themselves in jail, but not for their skating - for other even more random acts of crime.

All of these skaters have since been released and most of them now live a totally different lifestyle. One of the things they all share is that they were some of the top skaters of their day, skaters who pushed the boundaries of the culture on and off their boards.

If you don't know, now you know. Read this article to see which skaters missed out time at the benches because they were banged up behind bars.


Andy Roy was nicknamed 'The Snuggle Bandit' in jail, he's not scared to snake a guy on the top of a ramp or in the shower room. Andy Roy is so crazy, his tales of taking heroin on Anti Hero tours and his savage bloody style of skating really shows that he's prepared to put his body on the line and switch off his brain to land the tricks he wants.

Andy's time in jail seems to have been well spent, he even took a few cooking classes and now he's happily back alongside his bro's Julien and Cardiel over at the Anti Hero camp. It looks like he had a great time on their KOTR trip last year. Since his release, Andy has found time to make it on to the TMZ site which released footage of Andy getting tackled by security as he attempted to hug or 'snuggle' DMX, as X rapped live onstage. Andy Roy, skateboarding salutes you.


In Antwuan Dixon's Epicly Later'd episode we see 'Twuan become engaged in a series of heated confrontations with police, his behaviour and attitude foreshadowed the legal charges that would result in a three year prison sentence.

Throughout the show Antwuan tells us stories about getting off life charges and his love for his brother, a west LA gangbanger who was in prison. It seemed inevitable that Antwuan would one day follow in his footsteps, and sure enough he did.

It has recently been announced that Antwuan has been released from prison which is majorly positive news for the rookie pro, who is still only 25. His parts in Baker 3 and Baker Has a Deathwish were amazing, he's still got the potential to take the skate world by storm. Antwuan's insane relaxed natural style and devilish bag of tricks made his skating into an instant classic, so hopefully the skate world will get to see more from him in future.


Christian Hosoi was caught in a Hawaiian airport with a large amount of crystal meth and was placed in prison for his crimes. After serving his time, Hosoi emerged from prison a changed man, keen to uphold and promote his Christian beliefs and hungry to return to the skate game.

Hosoi hit up legends comps aplenty and his skating shows that his natural flair and ability on a board are still present, it looks like he hasn’t missed a beat when he skates, a sign of his experience and his personal commitment to skateboarding.

tas pappas

Tas Pappas was 1996 world vert champion and the darling of the Australian Vert skate scene. However after the suicide of his brother Ben, also a talented vert skater, Tas went off the rails.

Ben committed suicide in part due to depression relating to the decline of his skate career. It all went downhill for Ben after he was slapped with a lifetime ban from the U.S having been caught trying to smuggle cocaine through American customs, hidden in a DC shoe.

In 2008, Tas, mimicking Ben's action was also caught smuggling cocaine, which he hid under his griptape, into Australia from South America. He was imprisoned for 3 years.

Tas has been out of prison for a few years now, he's off drugs and back to skateboarding, knocking out tricks he's never done before. A documentary about Tas and Ben's life called All This Mayhem will tell you their side of the story. It's a savage tale of the liberating and intoxicating nature of skateboarding, Aussie brotherly love, drugs and overcoming adversity.


Shiloh had a fight with an enemy, got an assault charge and while he still had a warrant out for that was caught stealing at a local mall, meaning he ended up in prison for 10 years.

Shiloh had great sections as a young kid in World's Love Child and New World Order and came back after years in prison with a refreshing, well received section in TransWorld's First Love video.

Shiloh's ledge dancing skills felt fresh to newcomers in skating and older skaters were stoked to see his return. Although he was gone from the game for a long time, Shiloh and his skating has been relevant in the last three decades, and that's no easy task.

fabian alomar

Fabian 'Fabes' Alomar is a legendary Lockwood local and former pro skater for Menace Skateboards, a company headed by New York street skating icon Kareem Campbell. After taking a wayward route out of skate life and into a world of drug addiction, robbery and drug possession, Fabes was arrested made to serve an 8 year sentence.

When he got out, Fabes returned to the world of skateboarding, which welcomed him back with open arms, and he also discovered a talent and passion for acting. Fabes did a lot of networking and secured roles on mainstream TV shows like America's Most Wanted and Goldilocks. In May 2013, Fabes career plans were scuppered when he was charged with possession of a controlled substance while skating in Hollywood and he was taken into a detention center.

Faced with a sentencing of 26 years to life, a campaign called Free Fabes was started and it was successful, Fabes managed to be spared his sentence. With the help of a skate community behind him and his own personal determination, he managed to escape prison life and hopefully that will be the last we hear of Fabes and jail time for good.


Steven Cales started skating in New York with Keenan Milton,Gino and Huf. Cales was a notable member of the scene who never had the opportunity to film a full length part to do his skating justice.

Cales has been in and out of jail, and it seems his time in the pen has changed his life irrecoverably. Especially in the mid 90's when he'd just been offered the chance to act as himself in Larry Clark's film KIDS, but couldn’t do it due to being incarcerated at the time.

Also, In the early 00's he was charged with a series of violent crimes but managed to beat a 14 year rap that was reduced to just 20 months. It seem he's changed so much since those days but when remembering his jail time he must always think, what if?

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One night Jereme Rogers was somehow involved in a nightclub brawl, this resulted in him being mistakenly charged with assault. In combination with some outstanding prior traffic warrants JROG was given a 3 month prison. But due to his great legal assistance this sentence was reduced to just 7 days, a hand stand sentence.

On this whole list of skate jailbirds it seems Jereme is the only one who chats about his stint in jail as a badge of honour. Whilst in the pen for a week, he says he managed to meet fellow skaters, fans and even scumbag rapper Chris Brown. Whatever you think of the Sherminator it seems he really made the most out of his jail time on this one. Go figure.


Duane Peters has had a tumultuous time in skateboarding. The master of disaster has never been afraid to do what he wants on a board and takes that same energy to every other part of his life.

Living homeless and addicted to heroin for portions of his life, Duane spent many days in and out of L.A county jail. In this clip he gives a great breakdown about the seizures, drugs and beat downs that he saw there. Gnarly.


There's not too much to say here that Ali didn't say in his Epicly later'd with Patrick O'Dell. He clearly still grieves every day for the death of his friend and Flip Skateboards teammate, Shane Cross. Ali was imprisioned for his involvement in his friends accidental death.

Whilst he did make an appearance in Jaws 25 Stair Lyon clip, it seems Ali has taken some distance from skating.

His jail term was undoubtedly harsh, but it seems he has emerged as a clearer headed person. Hopefully he will skate again one day and we can get to see him do stuff like his wallie grab out the fin of London Bridge ten.