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Played By: Augustus Prew
- Badass Boast: Gives one to an international terrorist. Then acts on it.
- Hot-Blooded: He's prone to getting into fights, which is what led him to his incarceration.
- Lightning Bruiser: He can disarm an opponent with incredible speed. Unless it's A&W, that is.
- Only Known by Their Nickname: Michael refers to him as his "whip hand," and his real name (David Martin) is almost never referenced.
Played By: Rick Yune
- Badass Bookworm: He's extremely smart (even Michael calls him a genius) but is no slouch when it comes to fighting, either.
- Call to Agriculture: Decides to stay in the peaceful village of Phaeacia instead of returning to modern civilization.
- Functional Addict: His addiction is his biggest crutch. His stay in Phaeacia is part of his recovery.
Played By: Mark Feuerstein
- Big Bad: He was responsible for The Final Break, including Michael needing to fake his death.
- Bitch in Sheep's Clothing: Appears to be a regular milquetoast Nice Guy. Secretly a Manipulative Bastard mastermind.
- Devil in Plain Sight: So plain he outright married Sara.
- Kick the Dog: Threw away all of Michael's paper cranes to Sara that would have let her know he was still alive.
- Laser-Guided Karma: At the end of the series, he's imprisoned in Fox River just like the brothers at the start of the series, left to be murdered by T-Bag.
- Manipulative Bastard: Framed and incarcerated Michael so that he could marry Sara during his faked death, and brainwashes MJ into briefly turning against him; he also modifies MJ's drawings to Michael to lure Michael to the house.
- Oh, Crap!!: The look on his face when he realizes Michael set him up and framed him for the murder he originally framed Michael for. Again when he is sent to Fox River and sees who his cellmate is.
- Smug Snake: Cannot stop taunting Michael and holding his family over his head.
- The Sociopath: He only cares about how much he can control Sara and MJ.
Played By: Kunal Sharma
- Action Survivor: He survives almost being lynched in prison and multiple scrapes with death during and after escaping from prison. Sadly it doesn't last
- Bury Your Gays: Cyclops ends up shooting him to death.
- Likes Older Men: His lover was a friend of his father's, after all.
- Sacrificial Lion: He's the first official teammate to die and does so protecting Michael.
- We Hardly Knew Ye: He only makes it through a few episodes before he's killed off.
Played By: Inbar Lavi
Played By: Numan Acar
- Beardof Evil: Sports a very Bin Laden like beard, which is appropriate for a Radical Terrorist.
- Insane Equals Violent: He is a religious fanatic who thinks nothing of public execution of "infidels" and homsexuals, torture, rape and war crimes, and thinks he is justified in doing so in the name of God. Sadly for the real ISIL this is Truthin Television.
- Youhave Outlived Your Usefulness: After they help him escape from Prison he attempts to pull this on Michael and his group.Thanks to Lincoln and Whip it doesn't work.
Played By: Amin El Gamal
- Evil Former Friend: To Sheba.
- Eye Scream: Sports an eyepatch after attempting to rape Sheba as a youth. Loses the other one via scredriver thanks to Michael.
- Fate Worse than Death: Instead of killing him quickly, Michael stabs him in the other eye and leaves him to die slowly in the desert.
- Love Makes You Evil: Had a crush on Sheba, but tried to rape her when she turned him down.
- Poison Is Evil: He manages to cut Michael with a poisoned blade while the two are struggling, leaving Michael near death in the next episode.
- Rapeisa Special Kindof Evil: See Love Makes You Evilabove.
A&W and Van Gogh
Played By: Marina Benedict and Steve Mouzakis
- Atrocious Alias: Let's just say they didn't have the most popular aliases among viewers.
- HeelFace Door-Slam: Van Gogh starts to suspect Michael's innocence and tries to stop A&W from shooting him and his son, but she shoots Van Gogh instead and leaves him for dead. Subverted as he does give information to Sarah when he lays dying in the hospital.
- Punch-Clock Villain: Both of them want to escape, but A&W is resigned to the fact that there's no leaving 21-Void.
- Redemption Equals Death: For Van Gogh. In hospital, while he is on life support and unable to speak he manages to give vital information to Sarah before presumably dying offscreen.
- Those Two Bad Guys: Almost never seen apart.