Prison Break brims with tragedy, with plenty of material to set the stage for truly gut-wrenching scenes. Centering on two brothers who must navigate criminal activity, conspiracies, and prison life, many of the show’s most heartbreaking moments occur in the aftermath of bad choices and forever-lost second chances. Empowering these scenes are characters who remain deeply relatable despite their questionable decisions.

With its revolving door of enemies-turned-allies, Prison Break offers its most monstrous characters an opportunity to showcase their humanity. At its core, the show’s pervading theme is that there are no heroes and that everyone is capable of criminal behavior if thrust into the right (or wrong) conditions. By challenging traditional concepts of good and evil, Prison Break characters are painted in murky shades of gray, providing a compelling exploration of morality and human nature.

10Haywire Jumps To His Death

Prison Break Season 2, Episode 16: “Chicago”

Charles “Haywire” Patoshik jumping to his death highlighted how tortured he was. After becoming a Fox River Eight, Haywire is apprehended again when he protects Sasha Murray by killing her abusive father. Later, Alex Mahone finds Haywire huddled atop a grain elevator and discerns that Haywire killed the abusive father because he was a victim of abuse himself. Recognizing that Haywire needs to be in police custody despite his distress, Mahone helps Haywire come to the conclusion that he can escape Fox River by jumping to his death. It’s a heartbreaking scene for a character the world had broken long before his body hit the ground.

9Aldo Burrows Tells His Sons He Loves Them Before He Dies

Prison Break Season 2, Episode 12: “Disconnect”

Aldo Burrows’ death carries emotional weight due to his familial ties with the main characters, Michael Scolfield and Lincoln Burrows. Despite Aldo’s flawed past, his deep love for his sons is evident. Thanks to his history with the series’ primary antagonists, The Company, he’s forced to leave his family to ensure their safety. After Aldo is shot by Alex Mahone, the trio tragically fails to reach a hospital in time. Before succumbing to his injuries, he rests his head on Michael’s shoulder and tells his sons that he loves them. This tragic moment reaffirms their convictions to fight but also reminds them of what they might lose along the way.

8Brad Bellick Sacrifices Himself To Save Lincoln Burrows

Prison Break Season 4, Episode 10: “The Legend”

Brad Bellick is introduced to the series as a relatively unlikeable character, but his evolution over the course of the series makes his sacrifice for Lincoln Burrows one of the hardest pills to swallow in the entire show. Initially, an antagonist for two seasons before evolving into a genuine friend, Bellick’s character arc is a slow burn. Engaged in a daring plan to infiltrate The Company’s headquarters by crafting a tunnel in a water pipe, Bellick sacrifices himself when the pipe floods. His tragic death showcased the remarkable depth of his metamorphosis from a sociopathic antagonist to a dedicated protector of his friends.

7Christina Scofield Imprisons Donald Self In A Vegetative State

Prison Break Season 4, Episode 21: “Rate of Exchange”

Donald Self is not the most likable character in Prison Break, but his ending is arguably the worst in the entire show. Initially an ally, Self betrays Michael Scofield by stealing the Scylla card for personal gain. The show unveils the personal tragedy of Self’s comatose wife in New York before he’s finally arrested. However, because he refuses to disclose the brothers’ whereabouts, Christina Scofield injects him with the same chemical that left his wife in a vegetative state. Self lives out his days in a similar condition, and although he certainly deserves some sort of comeuppance, eternal locked-in syndrome is pretty harsh.

6Wyatt Matthewson Kills Alex Mahone’s Son, Cameron

Prison Break Season 4, Episode 1: “Scylla”

Alex Mahone remains one of the most enigmatic characters throughout Prison Break, but when he learns that Wyatt Matthewson tortured and killed his 5-year-old son, the news is shocking, appalling, and heartbreaking. Although there are many instances where Mahone’s actions are reprehensible, Wyatt Matthewson is a monster from his first scene to his last. Mahone continues to exhibit a unique sense of empathy for many of his victims. Though it rarely causes him to stay his hand, his empathy suggests he’s a far more complex character and isn’t specifically evil. His son’s death is more than tragic, even if his father is often the villain of the piece.

5Whip Dies In Front Of His Father, T-Bag

Prison Break Season 5, Episode 9: “Behind the Eyes”

Whip’s background remains a mystery for quite some time when he begins working for Michael Scolfield in season 5, but when he finally gets to meet his long-lost father (who turns out to be T-Bag), his death soon after is shocking and exceedingly tragic. Despite Whip’s brief presence, he quickly becomes a likable character. In an unexpected and heartwarming scene, he meets his father in the series. Joining forces with T-Bag to free Michael from Poseidon, Whip is tragically shot and killed in season 5. Whip’s sad and abrupt end adds an unexpectedly heartbreaking touch to the story, revealing a deeper emotional layer to one of the series’ major villains.

4Fernando Sucre Is Imprisoned In Sona To Protect Michael Scofield

Prison Break Season 3, Episode 13: “The Art of the Deal”

After helping Michael Scofield escape from Sona, Fernando Sucre is captured by Sona guards, tortured, and eventually imprisoned for refusing to give up Michael’s location. Throughout the series, Sucre’s loyalty to his friends, especially Michael, is an indelible facet of his character. Shortly before he sets his plan into motion, he makes a tearful call to his lover, Maricruz Delgado, where he apologizes for choosing to help Michael before returning to her and their daughter. His torture and imprisonment at the end of season 3 are made worse when his friends aren’t made aware of his situation until several months later in the following season.

3Charles Westmoreland Dies Before Seeing His Daughter

Prison Break Season 1, Episode 21: “Go”

When Charles Westmoreland dies, it’s especially tragic because his reason for attempting to escape Fox River was simply that he wanted to visit his terminally ill daughter before she died. Westmoreland was a kind individual against the backdrop of Prison Break’s army of convicts, with a valuable knack for avoiding trouble with inmates and Fox River guards. He initially refuses to join Michael Scofield’s efforts to escape, but after learning his daughter was sick, he finally relents and joins Michael’s P.I. crew. While it’s sad that Westmoreland dies, it’s worse that he was unable to see his daughter one last time.

2Veronica Donavan Is Executed By Agent Blondie

Prison Break Season 2, Episode 1: “Otis”

Veronica Donavan’s death at the hands of Agent Blondie was one of the worst character deaths in the series. Flashbacks in the first season establish that she had a hand in helping Michael decide to rescue his brother since the two had been estranged for a time prior to the beginning of the series. Unfortunately, after discovering that Terrence Steadman’s murder was staged, proving Lincoln’s innocence, she calls the police for help only to realize that the police were undercover agents with The Company, and she is subsequently killed. Veronica Donavan’s death is among Prison Break’s most shocking events, especially heartbreaking since was a genuinely good person.

1Alexander Mahone Kills Tweener

Prison Break Season 2, Episode 7: “Buried”

David “Tweener” Apolskis’ death is another tragic end to another tragic character in Prison Break. He is sent to Fox River State Penitentiary for grand larceny after authorities investigate him for pickpocketing only to discover he had stolen a highly valuable Honus Wagner T206 baseball card worth $300,000. Tweener found himself in a series of unfortunate events after struggling to make allies at Fox River. While his actions lead to serious consequences for the series’ main characters, it’s made worse because he trusts the wrong people but never means to do harm. When Alex Mahone finally kills Tweener, it’s a pitiable end for a thematically unlucky character.