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In Prison Break, Charles Westmoreland was never meant to stand out. He fed a cat, mentored a younger inmate and kept mostly to himself. He wasn’t the loudest or the most dangerous among the ten men trying to break out of Fox River, but when the moment came, he got as close to freedom as anyone could, bleeding to death inches away from the window that could have saved him.
Besides, he seemed harmless and too old to matter much. However, the truth hidden behind those quiet eyes tied him to one of the biggest unsolved crimes in American history. His gentle manner and steady tone masked a past that stretched far beyond prison walls. While most of Prison Break lived in the realm of fiction, Westmoreland’s story came with roots buried deep in real events.
The Real Story Behind Charles Westmoreland and D.B. Cooper
Long before Westmoreland shuffled across the prison yard, the world knew him by another name and that is D.B. Cooper.
In 1971, Cooper hijacked a plane, walked off with $200,000 of ransom and jumped out of the plane with a parachute into the night sky as per Screenrant. Ultimately, none of the efforts made by the FAA or FBI were fruitful and no one could ever find him or conclusively prove he survived the jump. But in Prison Break, that mystery found an answer. Westmoreland carried proof of who he used to be, tucked away until the time was right.
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How Charles Westmoreland’s Secret Became Key to Michael Scofield’s Prison Break Plan
Westmoreland kept denying his real identity but when Michael needed help, he came clean. He had money stashed away that more than anyone had guessed and it amounted to five million dollars which was kept hidden in Utah.
Michael, always two steps ahead, had already figured it out. His plan wasn’t only about breaking out but about gathering everything he needed, including the likes of loyalty, a plane and most importantly, money to vanish after. Westmoreland, who succumbed to his injury during the escape, gave Scofield that final piece.
Charles Westmoreland’s Past and the Tragic Reason He Tried to Escape
D.B. Cooper supposedly landed badly back in the day before he limped away and stole a car only to crash it later on. That crash killed someone, and it was what led to Westmoreland’s long sentence. His knee never healed and his daughter, Anna, grew up while he served time, and when he heard she was dying from cancer, something shifted within him. Westmoreland wasn’t escaping for himself, he just wanted to see her one last time. And that hope pulled him into Michael’s plan.
Unfortunately, as we all know he didn’t make it. The show stretched belief more than once and not everything added up. Michael had promised to find Westmoreland’s daughter, and give her family some of the money. But nothing came of that. The story forgot her, like it forgot many things.
The Five Million Dollar Chase After Westmoreland’s Death
When another inmate overheard the secret about the money, he talked and the guards got involved. That set off a chain reaction that sent everyone chasing the same prize. The second season turned into a hunt for Westmoreland’s cash. T-Bag stole it while Bellick and Geary followed and it kept slipping through everyone’s hands. Eventually, even Michael and Lincoln got it, only to lose it again after it was pushed into the sea by Agent Kim.
Among murderers and liars, Westmoreland stood apart. He was the one who had already run from the world once and got caught in its grip again. His story connected a made-up prison break to a real man who vanished into a storm and became a legend.
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