15 Greatest Prison Break Characters, Ranked

It is time to unlock the cells and stand by your bunks, because Prison Break is back!

Paul Scheuring’s gripping drama originally aired four dramatic seasons over on Fox between 2005 and 2009. The plot revolved around Wentworth Miller’s brilliant Michael Scofield, a structural engineer who had himself incarcerated at Fox River Penitentiary on purpose. The reason? Michael’s brother, Lincoln Burrows (Dominic Purcell), was facing the death penalty for a crime he didn’t commit.

More famous for Scofield’s tattoos that the plot itself, Prison Break was its very own Great Escape as Michael used an intricate series of blueprints tattooed on his body to map their escape. Nothing was ever as simple as that and various inmates, guards, and government agents were there to hinder the brothers on their road to freedom.

With a near-perfect ending, many are wondering whether Prison Break should really return. However, looking at the rogues gallery of lovable and loathable characters, it is hard to see why not. With that in mind, here are the 15 Greatest Prison Break Characters, Ranked.

15. Henry Pope

Who didn’t love an audience with the Pope? Henry Pope was the kindly warden of Fox River. Normally we are used to corrupt wardens who abuse their power, but Pope was a welcome exception to the rule.

Scofield and Pope first came together over Pope’s anniversary, when the warden was seeking the perfect gift for his wife Judith – he asked for Michael’s help in completing his matchstick Taj Mahal. As the inmates attempted to escape, a saddened Pope was shocked when Michael held a shank to his neck and demanded that Lincoln Burrows be released from solitary confinement.

Pope lasted 18 years before resigning due to the escape of the Fox River Eight. Although there were sporadic appearances after he left his role of warden, Pope was most notably there when Michael discovered the thumb drive that proved his brother hadn’t killed the Vice President’s brother. After originally telling Michael to turn himself in, Pope finally realized what it was all about and advised Michael to keep fighting.

Pope miraculously made it out of the show unharmed, which was a rarity for anyone in Scheuring’s world. Just like Charles Westmoreland, Stacy Keach’s role was a much-needed father figure to Michael.

14. Lechero

While the likes of John Abruzzi and Theodore Bagwell lorded it up over at Fox River, Panama had a very different prison system and was ruled by the muscular Lechero. Played by Robert Wisdom, no one character on the show was more intimidating than Sona’s supreme leader – whose real name, oddly enough, was Norman.

The backstory was that Lechero’s mother had been a maid for a very rich man who raped her. Seeing that justice was done, Norman disguised himself as a lechero (milkman) and killed him. From a young age he started taking drugs and soon became a drug kingpin in Panama, which also led to his incarceration.

Lechero was initially mistrusting of Michael, and he had every reason. When outsmarted, Lechero was shot by the guards during an escape and then rescued by Bagwell and Brad Bellick. After conning money out of Lechero, T-Bag saw his chance and suffocated the leader with a pillow to take his place.

With his uncompromising iron fist and manic laugh, Lechero was enough to make anyone’s skin crawl. However, it is his powerful connections and dramatic demise that make him one of the best villains of Prison Break.

13. Charles Westmoreland

While the “Is he D.B. Cooper?” mystery was about as flimsy as Prison Break plots could get, Muse Watson’s role as Charles Westmoreland was more than just an old timer with a penchant for cats. Just like Brooks in The Shawshank Redemption, the death of Charles was on the cards from day one, but it still didn’t make it any easier.

The longest-serving inmate at Fox River, Westmoreland was incarcerated for vehicular manslaughter, however, his story was much more interesting. He was actually infamous hijacker D.B. Cooper, who stole $5,000,000 before leaping from the back of an airplane. Much of season 1 involved Westmoreland refuting the claims, but we all knew it was true.

After the escape, Charles intended on seeing his terminally-ill daughter one last time – sadly, he would never make it that far. After being injured by a piece of glass, Charles bled to death in the infirmary moments before freedom. In his last act, Westmoreland told Michael where to find the money and wished him luck.

As a father figure to Michael, Westmoreland was just too nice for a show like Prison Break. Despite his early demise, the legacy of Westmoreland lived on long after he did, with most of season 2 involving the inmates trying to locate his treasure. Fans got one last treat when Watson reprised the role for a dream sequence in season 4.

12. Caroline Reynolds

There have been some notably corrupt presidents over the years (both in and out of fiction), however, Caroline Reynolds is one of the sassiest. With her razor sharp put-downs and bobbed haircut, Reynolds’ role was kept a mystery until her big reveal in episode 8. The big twist? Reynolds was the current Vice President and her brother was the man “murdered” by Lincoln Burrows.

We went down the rabbit hole to unravel the conspiracy surrounding Reynolds and those around her, including Agent Paul Kellerman as her own personal lap dog. While at first working alongside The Company, Reynolds soon branched out on her own when they threatened to pull their support for her political career. Determined to do it her way, Reynolds seemed to orchestrate the death of the current president and then headed to the White House.

However, everything came tumbling down when she was blackmailed into exonerating Lincoln due to “compromising evidence” about her relationship with her brother and him still being alive. Agent Kim intervened, so before Reynolds could free Lincoln she feigned illness, resigned from the presidency, and was never seen again.

Venomously selfish and with the warped implied incest with her brother, Reynolds was pure James Bond villain gold who bowed out far too early. Move over, Frank Underwood!

11. Benjamin Franklin

The first of many cheesy prison names, Benjamin “C-Note” Franklin was Fox River’s wheeler-dealer. You want it, Franklin could get it for you. The soft-hearted member of the group was one of the more honest crooks of the escape crew, only wanting to get back to his family.

Discharged from the army after discovering corruption, Franklin found himself on the inside after turning to a life of crime to provide for his family. Although he initially just wanted to return home, greed eventually got the better of Franklin and dollar signs rang in his eyes. After escaping Fox River, he joined the others in the hunt for Westmoreland’s money, then took his family on the run too.

When his wife and daughter were apprehended, C-Note was forced to turn himself in and cooperate with Mahone. Under pressure from The Company, Mahone was ordered to kill Franklin but instead told him to hang himself. Promised a relocation under the Witness Protection Service, Franklin and his family went into hiding with new aliases for a happy-ever-after.

Sadly, the deal fell through and C-Note returned for the final episodes of Season 4. Working alongside Agent Paul Kellerman and as a UPS delivery man, Franklin still held up his reputation of being able to get anyone anything. Franklin will be a key member of the revival series, however, he as undergone somewhat of a character change and converted to Islam.

10. Sara Tancredi

One of the most important, but also divisive parts of Prison Break is Sarah Wayne Callies as Dr. Sara Tancredi. While some fans would love to erase her, let’s not forget that the boys would still be rotting in Fox River if not for Dr. Tancredi.

Doe eyes across the infirmary made it clear that Sara and Michael would end up locking lips, however, we never really expected her to literally let him walk out of prison. In season 2, a beaten-down Sara was a changed woman but also a more determined one, who had no hesitation in killing Agent Kim to protect the brothers.

It was around this time that Callies announced her pregnancy and the character was briefly written out. However, unable to agree a new contract, Tancredi was spectacularly killed off in season 3 and Lincoln was presented with her decapitated head in a box. The show lept over the shark when it brought Sara back for season 4 in a move that some viewers still refuse to get on board with.

Sara was always trying to live up to high expectations, while Governor Tancredi was so blinded by his political career, he ignored the daughter in front of him. There is no denying that Dr. Tancredi was a complex and well-written character, it’s just a shame that behind the scenes trouble interfered with her arc.

9. Brad Bellick

Providing much of the comedy value, Wade Williams was perfect as corrupt correctional officer Brad Bellick. The balding, overweight bully definitely had a bark worse than his bite. Looking at the Brad from season 1 and the Brad who departed in season 4, Bellick had one of the most rewarding story arcs and also the most tragic.

When Bellick discovered Scofield’s plan towards the tail end of season 1, it looked like the jig was up, however, he soon found himself tied and gagged with no way of calling for help. Once the cons had escaped, the comedy duo of Bellick and Geary went on their own bounty hunt while looking to snag the reward money.

Williams really came into his own when Bellick (conveniently) joined the rest of the characters in Sona. It was a fall from grace from his Fox River days and Williams spent most of the season in some ill-fitting Y-Fronts. Sadly, things never got better for Bellick and his dramatic sacrifice to save the others in “Greatness Achieved” showed just how far the scumbag had come.

Looking at the roster of formidable villains who faced the brothers by the time the show bowed out, it is slightly laughable to think that Bellick was actually the first antagonist of the show. He may not have been as intimidating as the likes of Mahone or General Krantz, but Bellick had one thing by the bucket-load that set him apart from the others – his rat-like cunning.

8. Gretchen Morgan

Jodi Lyn O’Keefe’s Gretchen Morgan was the best thing Prison Break could’ve introduced in its waning third season. Sure, we had seen the tough men of The Company, but all we really needed was a woman’s touch. 

As a former soldier and current high-ranking operative for The Company, it also turned out that Morgan had a creepy relationship with General Krantz, and even bore his child. Shown to be one of the most resilient members of the cast, Morgan’s refusal to break down during torture in the Iraq War made her one particularly dangerous customer.

Although Gretchen was originally to blame for the death of Sara Tancredi, it turned out that even the show’s most vicious character couldn’t actually go through with the deed. Nevertheless, Gretchen still owns the show’s very own Se7en moment.

Hard-faced to the extreme, Gretchen really was a bad egg and more than deserved her incarceration at the show’s end. Scheuring had planned on doing an all-female spin-off titled Prison Break: Cherry Hill. It would’ve had a middle-class housewife at the center and was rumored to also include Gretchen behind bars; sadly the 2007-2008 Writers Strike cancelled all plans for Cherry Hill.

7. Paul Kellerman

Paul Adelstein’s sinister Paul Kellerman was the first “suit” we met in the series. Apart from Michael and Sara Tancredi, he was also involved in one of Prison Break’s most ludicrous resurrection plots.

Assigned to Caroline Reynolds as her Secret Service agent, Kellerman had a pivotal role in the Burrows framing and did everything in his power to cover up the truth. Often acting for the good of the masses and with an unwavering loyalty to Reynolds, Kellerman was seen still by her side after their assassination of the President. However, he was shown to have a heart when struggling to kill his partner Danny Hale and refusing to murder Sara Tancredi.

Kellerman was disavowed in season 2 and spent the rest of the series on the run as a rogue agent. He tried to expose the conspiracy surrounding Burrows but was “gunned down” when his transport convoy was intercepted. As we all know, this was just another ruse and a cheerful Kellerman returned in season 4 alive and well.

Not quite a villain, but definitely not an ally, Kellerman’s role was crucial to the early days of the show, while his miraculous return for the season 4 finale was a faithful nod to ridiculous conspiracies of Prison Break – remember, if you don’t see a body, they aren’t dead!

6. Alexander Mahone

The pill-popping and bug-eyed Alexander Mahone made Prison Break’s second season successful. While most shows would’ve floundered so far from their original premise, Mahone’s manhunt of the Fox River Eight kept everyone on their toes. William Fichtner’s unhinged menace may have softened as the show continued, but it still didn’t stop the fear that Mahone might bury you under his bird bath.

Introduced in the season 2 premiere, Special Agent Mahone’s sole task was getting the men back behind bars – something that he frequently failed at. As a morally grey character, we saw just how uncompromising Mahone was when he murdered David “Tweener” Apolskis in cold blood. Something wasn’t right with Mahone, and in one of the show’s best episodes, we came to realize that he was haunted by the memory of Oscar Shales, a murderer who he struggled to capture and subsequently buried in his backyard.

With Mahone’s sharp mind and sharper tongue, Fichtner’s absence from the revival is a huge blow to long-term fans of the show. You have to sympathize though; Scheuring said that not bringing Mahone back was the only way his story arc made sense.

Intellectually matched, Mahone was the yin to Scofield’s yang and a more than worthy adversary, even if they did put their differences aside. Fichtner certainly brought an intense performance to Prison Break and is still one of the best crafted FBI agents on television.

5. Lincoln Burrows

Dominic Purcell played the hot-headed Lincoln Burrows to a tee. Wrongly incarcerated for the murder of Terrence Steadman, it was Lincoln’s trip to Death Row that brought Michael for Fox River. While the various relationships between the characters changed over the course of the show, Lincoln and Michael’s brotherly bond remained a constant of the series.

While Lincoln wasn’t the sharpest tool in the shed, he always had a backup plan for when his brother wasn’t around to do the thinking – just like the episode “Bang and Burn” where he stole a plan from Macaulay Culkin in Home Alone. It is a known fact, though, that Burrows was much better at bringing the brawn than the brains.

The loveable lug-head had a few romances along the way, but dating Linc was a dangerous game and his association cost the lives of ex-wife Lisa and hotshot lawyer Veronica Donovan. Thankfully, Lincoln did find romance with Sofia Lugo and appeared to live happily ever after with his son L.J. when the show wrapped.

By season 4, Linc had grown into full-blown Company Agent, shooting first and asking questions later – thankfully he put down his pistol and tried to return to some form of normality. Scheuring was originally skeptical of Purcell, but he won on his acting skills and a quick head shave. Being so perfectly cast, it is hard to imagine that Purcell was the last member of the main cast to join, just three days before shooting began.

4. Fernando Sucre

Suave Fernando Sucre quickly placed himself as Scofield’s BFF inside the walls of Fox River. The cuddly Puerto Rican was doing everything for love, while whether  Sucre would ever get to be with Maricruz was about as close to a Ross/Rachel romance as Prison Break was going to get.

It became tit for tat between Michael and Sucre to see who could save the other more times. Michael saved him from drowning under a tree and so Sucre saved him from a coyote (what else). However, by the end of the second season, Sucre’s fate was left open when he was stabbed in the chest by T-Bag.

Obviously surviving his injuries, Sucre remained the last member of the Fox River Eight at large and proved influential in the attempted escape from Sona. Getting a job as a gravedigger, Sucre damaged the prison’s electric fence to aid Michael’s escape but also ultimately ended up locked inside the Panama hell-hole.

Amaury Nolasco brought heart and soul to the show, with his only real aim being areturn to normal life and find his baby. As expected, Sucre will be once again joining season 5, hoping to discover the truth on Michael Scofield, so we can’t wait to see his big grin again.

3. John Abruzzi

Serving life as the big bad mob boss, Peter Stormare’s John Abruzzi was not a man to be messed with. Put inside by Fibonacci the snitch, Abruzzi’s tale often revolved around his dogged desire for revenge.

As Fox River’s resident celebrity, Abruzzi ruled with an iron fist– well, until Theodore Bagwell slit his throat and seemingly put him out to pasture. With a physical and religious resurrection, Abruzzi was back and more determined than ever to get out and “whack” Fibonacci.

Although he was officially part of the Fox River Eight, Abruzzi’s tenure was shorter than most. His relentless pursuit of Fibonacci lead him into a trap set by Agent Mahone. When given the choice of going back to Fox River or taking a trip to the morgue, Abruzzi’s final lines were pure Godfather perfection. Spouting “I kneel only to God. I don’t see him here,” Abruzzi went down in a hail of bullets.

Abruzzi also got two of the show’s most shocking moments from its earlier years; taking two toes off Michael Scofield to get the location of Fibonacci and removing Bagwell’s hand with an axe. Given that he took Prison Break in more of a Sopranos direction, it’s only sad that Abruzzi didn’t stick around longer!

2. Michael Scofield

Prison Break would never have existed without Michael Scofield, the boy with the prison tattoo. For 12 years we’ve watched Wentworth Miller scowl into the distance and wear long-sleeved t-shirts to cover for makeup artists who got bored of penciling on his body. Michael was the focal point of Prison Break and always one step ahead of his enemies.

It takes a strong man to get sent to prison to visit your brother and it takes an even stronger man to break him out of that inescapable prison. As the show went on and the dangers grew, Michael made the most of the friends and accomplices around him by always putting his engineering skills to the best possible use.

Even after Prison Break moved from life behind the bars of Fox River, Michael and his brother realized that their days were destined to a life on the lam. Even after five seasons of the show, it’s still impossible to crack Michael’s stoic facade and poker face.

Although Miller has gone on to be an accomplished writer on the likes of Stoker and appearing as fan-favorite Captain Cold in the Arrowverse, he will forever be known as the brains of the Fox River escape.

Once again Scofield becomes the center of the show in the revival, when all eyes will be on how he has cheated death once more.

1. Theodore Bagwell

If anyone has given a “helping hand” to Prison Break over the years, it’sTheodore “T-Bag” Bagwell – once described as one of the creepiest characters on television. Robert Knepper has oozed anti-hero charm across every season and is easily the most exciting part of Fox’s revival. However, it is still an enigma how a man with literally no redeeming features can have reached such fan-favorite status.

As the leader of the white supremacist group, T-Bag caused problems for Michael Scofield from day one. The real turning point for Bagwell was the amputation in the season 1 finale. From then on, T-Bag was on his own and out for revenge. A crudely reattached hand and the murder of a vet set Bagwell out on a lonely second season.

Frequently separating Bagwell’s story from the main cast was always a bold move; few characters could hold up a separate storyline. Luckily, Knepper did it with ease and even crossed over to the “unofficial” spin-off Breakout Kings.

From prostitute murder to pedophilia, ruling a Panama prison to bludgeoning someone to death with a prosthetic hand, you name it, Bagwell has done it. The slimy weasel is usually the one at bottom of the pack who somehow always floats to the top. Only time will tell how he fares in season 5, when see T-Bag return to his psychotic glory.

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