The 15 Most Tragic Moments In Prison Break

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.

15 Lincoln Receives Sara’s Decapitated Head

Prison Break Season 3, Episode 4:

One of the most shocking and saddest moments in Prison Break came in the season 3 episode “Call Waiting.” The Company had kidnapped Sara and LJ and held them as hostages to force Michael to break out from Sona with Whistler, which is when things went wrong. Lincoln tries to break her out but fails. Sara ends up being taken into a van, and LJ hears violent things happening, which leads to her apparent death.

Gretchen Morgan claims that she decapitated Sara, and they sent her head in a box to Lincoln as punishment. It was a horrible moment for Lincoln, who hid the fact from Michael because he still needed to save LJ. When Lincoln saw the head in the box, he almost vomited and realized things had gone from bad to worse. The reason for the head-in-the-box moment was that Sarah Wayne Callies was pregnant and chose to leave the show. In season 4, Prison Break retconned the moment by claiming it was a lookalike who was decapitated to fool Lincoln.

14 Brad Kills Westmoreland’s Beloved Cat Marilyn

Prison Break Season 1, Episode 8: “The Old Head”

Sometimes, the death of a beloved pet or animal is more tragic and sad than even the death of a human. There were so many deaths in Prison Break that it often became normal other than fan-favorite characters. However, one of the saddest moments in the entire series came thanks to the death of a cat. Charles Westmoreland owned Marilyn, and a grandfather clause allowed him to keep his cat in prison.

The cat saved Westmoreland more than once, as the DOC tried to transfer him more than once, but he used Marilyn to remain, thanks to legal loopholes that blocked his move. However, in the season 1 episode “The Old Head,” Westmoreland refused to reveal who killed a corrections officer named Bob in a riot. As a result of his refusal, Brad Bellick killed Marilyn. When Westmoreland went to his cell and found Marilyn dead on his bunk with Bellick looking on, it was a heartbreaking moment.

13 C-Note Attempts Suicide To Save His Family

Prison Break Season 2, Episode 16: “Chicago”

C-Note is an interesting character, as he starts antagonistic with the other prisoners but soon becomes a loyal member of the team. It turns out he was in prison for delivering stolen goods after he struggled to get a job when the military dishonorably discharged him for not covering up the fact they were torturing prisoners. This fact made him a conflicted and morally gray character. He reunited with his wife and daughter when he escaped, but things went wrong.

After his wife ended up arrested for harboring him and his daughter had fallen deathly ill, he turned himself into Mahone to ensure his family’s safety. However, when he served his purpose to The Company, Mahone told him to take his own life in prison or his family would die. Seeing the proud, strong man hanging himself in his cell to save his family was heartbreaking, but luckily, the guards saved him. He ends up testifying against Mahone and is allowed to enter witness protection with his family, so at least he gets a happy ending.

12 Michael Sacrifices Himself To Save Sara & Lincoln

Prison Break Season 4, Episode 24

In one of the most shocking moments in Prison Break history, lead character and hero Michael Scofield seemingly sacrificed himself to save his friends and loved ones. Season 4 ended with Michael electrocuting himself to ensure that Sara and Lincoln could get away. The season ends with everyone at Michael’s grave in a sad, tragic moment, saying their goodbyes. There was also a DVD Michael left them explaining his actions.

One more feature-length episode, titled Prison Break: The Final Break, showed how and why Michael sacrificed his life to save them and why it was important for them to move on without him. While tragic, this was how the series was supposed to end, and it was a melancholy conclusion to the story. The truth is that Michael faked his own death and was still alive for a fifth season that arrived later, but for the time when everyone thought he was dead, it was a sad, tear-jerking moment.

11 T-Bag’s Family Rejects Him

Prison Break Season 2, Episode 17: “Bad Blood”

Theodore “T-Bag” Bagwell was not a good person. The leader of the Fox River Eight and a white supremacist, he was a major antagonist within the prison and caused the heroes a lot of problems throughout his run on the show. When T-Bag learns that Michael is planning an escape, he blackmails his way onto the team. After his escape, a lot happens to T-Bag, and he doesn’t do much to redeem himself.

Even after losing his hand, he became more violent and killed several people, but in the end, he just wanted his family back. He finally found Susan and his kids, and it seemed he might settle down and just stop his illegal activities. That doesn’t happen because Susan and his kids reject him instantly and want nothing to do with T-Bag. Brokenhearted, T-Bag releases them to the police and goes on the run again. He’s not a character the audience wanted to feel for but even after his awful deeds, this was tragic.

10 Haywire 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. Mahone sadly helped Haywire make a decision that both played into his mental illness and also manipulated him at his time of need.

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. Haywire was not a bad person and his life was tragic by itself. His death just emphasized those points.

9 Aldo 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 Scofield 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. This scene was a tragic moment, but it was also important because the death and final confession emphasized how important family was for Michael and Lincoln.

8 Brad 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. It is almost hard to believe that the same man who killed an innocent cat in Marilyn, on top of many other people along the way, garnered so much sympathy when he finally died. He died even while Michael and Lincoln told him not to, and it was a strangely heroic moment for the former villain.

7 Christina 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. Seeing that Self’s actions were almost a way to try to help his wife was a devastating twist. In a heartbreaking moment, Self was listening when Keantz ordered the death of his wife, even though she was in a vegetative state.

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.

6 Wyatt 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. William Kim had already threatened Mahone’s son and hit him with a car. Then, in season 4, the unthinkable happened.

After his wife agreed to reconcile and try to restart their family, Mahone went home and found that Mathewson had gotten there first and shot and killed the five-year-old. 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.

5 Whip 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 Scofield 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. When A&W shoots and kills Whip in front of his father, it finally sends T-Bag over the line, and he sets out to gain vengeance rather than just continuing his life of senseless violence.

4 Fernando 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. Seeing this loyal man imprisoned and abandoned where no one knows where he is was a terrifying moment, and he deserved much better. Luckily, he ended up saved in season 4.

3 Charles 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 PI crew.

Westmoreland had a tough time on the series. He had his beloved cat, Marilyn, and Bellick murdered the animal and left it on his bed to find. This moment pushed him harder to help Michael, and his kind heart made it easy to see him get to see his daughter to say goodbye. Bellick caused his death as well, and his happy ending never happened. While it’s sad that Westmoreland dies, it’s worse that he was unable to see his daughter one last time.

2 Veronica 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.

Tragically for her, she realizes too late that the police were undercover agents with The Company. She lets the police in to protect her from Steadman, now knowing they are dirty cops. At that moment. Agent Blondie pulls out her gun and shoots Veronica in the head and twice in the chest. Veronica Donavan’s death is among Prison Break’s most shocking events, especially heartbreaking since she was a genuinely good person. It was fitting that Blondie died in the exact same way, when Mahone shot him in the head after rejoining The Company.

1 Alexander 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. He felt better connected to the Black population, but they rejected him because he was white.

This put him at odds with the white supremacists, who saw him trying to befriend the Black prisoners – which earned his nickname. While his actions lead to consequences for the series’ main characters, it’s worse because he trusts the wrong people but never means any harm. His end came when Mahone caught Tweener after the escape. Mahone shoots and kills Tweener in cold blood before giving him a secondary gun to make it look like self-defense. It’s a pitiable end for a thematically unlucky character.

Prison Break

Prison Break tells the story of two brothers who must unravel a political conspiracy while escaping from one of the most secure places on Earth. When petty criminal Lincoln Burrows (Dominic Purcell) is falsely convicted of murdering the Vice President’s brother, his own brother, Michael Scofield (Wentworth Miller), has himself incarcerated in order to stage a daring prison break using the blueprints of the facility he has tattooed on his body.  

Release Date

August 29, 2005

Cast

Curtis Lum , Sarah Wayne Callies , Marina Benedict , Amin El Gamal , Wentworth Miller , Steve Mouzakis , Dominic Purcell , Bobby Naderi , Christian Michael Cooper

Seasons

5