Prison Break gave some fan-favorite characters a different fate than the one they deserved. While occasionally heartbreaking for viewers, this made the show better, as part of what made Prison Break compelling was its unpredictability, with few characters being confirmed safe. At the heart of the show, Michael and Lincoln appeared to be untouchable. However, other members of Prison Break‘s Fox River Eight were not so lucky. Prison Break‘s four seasons, movie, and reboot all have a high death toll, and many of the show’s most shocking moments involve the deaths of characters previously considered safe.

Prison Break‘s main plot concerns Michael’s attempt to break his brother, Lincoln, out of death row. Over time, the escape plan grew more risky, with Michael seemingly in over his head as more people joined his team. Though some of Prison Break‘s characters, like T-Bag, are dangerous, having committed some disturbing crimes, others, like Tweener, were in the wrong place at the wrong time. Prison Break produced some fantastic acting performances and character development, with several villains switching sides. That said, there were both protagonists and antagonists who deserved better than their fates in the show.

10Veronica Donovan

Veronica Had The Potential To Uncover The Truth Before Her Shocking Death

Prison Break‘s female characters were flawed, but Veronica had the potential to be one of the most formidable in the show. As a lawyer, she knew how to work with the system, but it was her curiosity and a silly mistake that led to her early death. While investigating the government conspiracy that saw Lincoln Burrows falsely accused of murder, Veronica entered a strange, isolated house, and allowed the door to shut behind her, trapping her inside.

For a character so intelligent, with the connections and problem-solving skills to be an asset to Lincoln after his escape, this was a disappointing and anticlimactic ending for her.

Though it seemed that Veronica was going to talk her way out of danger or persuade Steadman to help her, she was shot dead in the first episode of season 2. Veronica is then barely mentioned, despite being one of the first characters to fight to clear Lincoln’s name. For a character so intelligent, with the connections and problem-solving skills to be an asset to Lincoln after his escape, this was a disappointing and anticlimactic ending for her.

9John Abruzzi

Abruzzi’s Death Was Iconic But Came Too Soon

John Abruzzi was one of the most interesting and essential members of Michael’s escape team. As a high-ranking mafia member, Abruzzi’s plane could have been the perfect getaway vehicle, but Michael did not take the shifting mafia politics into account, with Abruzzi fighting to keep his status throughout the show. Though it had seemed certain that Abruzzi would thrive while on the run, his death came too early and ended Prison Break‘s best chance at a spin-off.

Abruzzi’s death scene is one of the most iconic in Prison Break, with law enforcement shooting him down after he refuses to kneel for them. That said, his death should have come much later, with viewers getting to see him begin his planned escape to Italy with his family. With the current popularity of mafia and true-crime shows, an Abruzzi spin-off would likely have been well-received, and his death was a fitting but premature ending for the character.

8Gretchen Morgan

The Show’s Unbreakable Antagonist Deserved An Explosive Ending

Most of the first season of Prison Break cast the sadistic and opportunistic guards as the main antagonists. However, by season 3, the guards looked relatively harmless compared to the new villains. Prison Break‘s overarching villain was The Company, and as a former member, Gretchen was well-connected, extremely intelligent, and had a disturbing ability to withstand torture. While Gretchen faded into the background by the end of season 4, she returned in The Final Break, but was robbed of a fitting ending once more.

The Final Break sees Sara being sent to prison, where Gretchen is also being held. Though the two women have a bitter history, with Gretchen torturing Sara in the past, they team up to escape. When Gretchen is caught and fails to escape alongside Sara, this could have been the opportunity for an explosive ending. As Gretchen made an impression on virtually every other Prison Break character, her ending should have been as memorable as she was, yet she was presumably locked in her cell once more.

7Roland Glenn

The Character Never Reached His Potential

Prison Break became a completely different show by season 4, which had much more of a science-fiction feel than the first three seasons. As the team tried to track down the mysterious Scylla, Roland joined the team as a hacker. Introducing him in the first place might have been a bad decision, as most of the other characters were already known, with established dynamics. Roland could have found a place in the group, but he was written as abrasive and unlikable, which seemed an odd creative choice.

Roland had the potential to be a core member of Michael’s group. However, he did not get on with them, constantly shifting between trying to be included and being openly dismissive of the other characters. When he eventually apologized after getting shot while betraying Michael, it did not have the emotional impact that a character’s death should have had. Roland deserved to be given a chance but needed to be written as a likable character for this to happen.

6Sara Tancredi

Sara Spent Season 5 Being Manipulated Again

While Sara and Michael fell in love during Prison Break‘s season 1, she still spent the majority of the season being deceived by him. Two of Prison Break‘s three endings give their relationship a bittersweet ending by killing Michael. Despite this sad twist to their story, the two find happiness together first, which eclipses the original way they met. By retconning the first two endings, Prison Break undid this, with Sara being tricked by another man.

IMDB’s Highest Rated Episodes of Prison Break

Episode Number
Title
IMDB Score

S1.E21
Go
9.5

S1.E22
Flight
9.3

S1.E6
Riots, Drills and the Devil: Part 1
9.2

In Prison Break‘s rebooted season 5, with Michael believed to be dead, Sara has remarried, but her husband is not what he seems. As Michael and Sara’s relationship is central to every season of Prison Break, seeing her with another love interest was jarring. That said, she deserved to find happiness and needed a better storyline than being deceived by a different partner. It is possible that the season was written to give Sara and Michael a happy ending, but the Jacob storyline did not do her justice.

5Alex Mahone

The Fan Favorite Character Did Not Deserve To Lose His Son

FBI Agent Alex Mahone first appeared in Prison Break as the show’s most formidable antagonist, with intelligence and problem-solving skills that matched Michael Scofield’s. He was one of the most interesting and complex of Prison Break‘s characters, and yet Mahone was not in Prison Break season 5. The show’s creator, Paul Scheuring, didn’t know what to do with the character, and some viewers may think that there had already been enough done to Mahone.

Though Mahone was great at his job and a very strong ally to any team he was on, his greatest ambition was to leave his work behind and pursue a normal life with his family. This possibility is taken away from him in season 4 when his young son is murdered. Prison Break often killed off characters, but killing Mahone’s son felt gratuitous and while it led to an excellent revenge scene, Mahone deserved a break from his many struggles.

4David “Tweener” Apolskis

Tweener’s Punishment Did Not Fit His Crime

Tweener often got overlooked in favor of more charismatic characters like T-Bag and Abruzzi, but his backstory was one of the most tragic in Prison Break. Tweener was a small-time pickpocket and thief, but stealing a collectors’ baseball card led to him being charged with grand larceny. From the moment he entered Fox River Penitentiary. Tweener was out of his depth, which led to him making unwise decisions out of fear.

That said, while Tweener was far from being the smartest character in Prison Break, it was clear that he deserved a better fate than the one he got. If he had not betrayed Michael and his team, Tweener could have become smarter and braver through spending time with the rest of the group, with the potential to be more like Sucre. However, Tweener was killed by Mahone after leading the FBI away from Michael, with his death being one of the most tragic moments in Prison Break.

3Charles Westmoreland

Prison Break’s Most Tragic Character Died Within Reach Of Freedom

Westmoreland is the only Prison Break character who is based on a real person, and it was tragic enough to see the character stuck in prison after the daring heist that he pulled off decades ago. That said, his incarceration was only the beginning, as Westmoreland was wronged repeatedly throughout season 1 of Prison Break, leading to the saddest death in the show. Westmoreland had adapted to prison life, but his daughter’s illness was the catalyst for a fate that he did not deserve.

As he had been one of the kindest characters in the show, this fate was one of the most painful and undeserved in Prison Break.

Though he originally wanted no part in the escape, Westmoreland joined Michael’s group when he learned that he would not be allowed to leave prison to visit his dying daughter. When a piece of glass injured him during a fight with Bellick, his slow death left viewers hoping for a miracle, but Westmoreland died within reach of escape. As he had been one of the kindest characters in the show, this fate was one of the most painful and undeserved in Prison Break.

2Charles “Haywire” Patoshik

Haywire Was Manipulated By Mahone

Haywire is one of the more unusual and complex characters in Prison Break. Season 2 showed that he is capable of extreme violence, but that his anger appears only to be directed at abusers. Haywire’s morality code, childlike wonder, and simple ambition to go to Holland made him a fan favorite. If he had been in Prison Break for longer, a Haywire spin-off could have gone in any direction, with the character having adventures while on the run.

Prison Break‘s season 2 brought out the best in Haywire and the worst in Alex Mahone, as Mahone manipulated Haywire into jumping to his death. This scene was not only one of Prison Break‘s most shocking moments, but it felt deeply unfair to a character who was so compelling and fun to watch. Haywire gave Prison Break some of its funniest scenes, which were often needed to break up the tension in season 2.

1Michael Scofield

Michael Went Out On His Own Terms (& The Reboot Should Not Have Retconned This)

Despite having Lincoln’s support and Veronica fighting for him, Michael often seemed to be one of the loneliest characters in Prison Break. This was later explained through his low latent inhibition, which made him think differently from everyone else. The responsibility of the escape and then of keeping Lincoln and Sara safe often weighed on Michael, and while Prison Break‘s season 5 gave Michael and Sara a happy ending, this may not have been the best choice.

Prison Break has two endings in which Michael dies, with season 4 implying that his brain tumor killed him and The Final Break showing Michael sacrificing himself for Sara. However, Prison Break season 5 undoes both these endings, with Michael faking his death and ending up in another prison. Though he gets a happy ending, this plot was unnecessary, and it would have been better if Michael had died on his own terms without the out-of-character decisions in Prison Break season 5.