Why Neal Caffrey Escaped Prison In White Collar Months Before He Was Due To Be Free

Neal Caffrey kicks off White Collar making one of the weirdest decisions for any prisoner when he escapes prison months before his official release date. White Collar began airing back in 2009. However, unlike any other crime drama, or fun buddy cop story, White Collar began with an incredibly compelling story where a career con man whose intelligence meant he evaded capture for years, makes the incredibly stupid choice to break out of prison a few months before his sentence is served.

While less intelligent criminals may grow tired of their confinement, a man with so much on the line like Neal Caffrey could really use a clean slate, and if he simply finishes the remainder of his four-year-long prison sentence, he would be free and clear. Instead, he chooses to run at the very moment when it looks like he is almost over the finish line. No sane person would do that, much less a criminal mastermind, so what made him do it?

Neal Caffrey Escaped Prison Because His Girlfriend Was In Trouble

Neal Caffrey Decided To Make His Escape For Love

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Like many of the most popular stories, it was all for a girl. Prior to being captured, Neal began a relationship with the lovely, yet dangerous Kate Moreau. Kate, played by Alexandra Daddario, learned how to con from Neal while the pair were dating, but the pair became estranged for some time. While Neal tried to get Kate's attention, he performed bigger and more ambitious jobs, eventually leading him back to his beloved Kate, but it was at this point that Neal was captured by the FBI and locked away for four years.

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Throughout that time, Kate visited him, and wrote letters, but when she stopped just three months before Neal was due to be free, Neal couldn't simply wait to find out what was happening. Neal broke out of prison, proving how easily he could have done so earlier if he had the proper motivation. Then, he was off in search of Kate, to make sure that she was still OK, and trying to determine what her true feelings were. Ultimately, he was unsuccessful in finding his former flame, but that didn't mean his search came up empty-handed either.

Neal Caffrey Gave Himself Up After Finding A Message From Kate

Kate Sent A Hidden Message To Neal In White Collar

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Neal went to a spot where the lovers had agreed before to meet so they could run away together. When he arrived, all he found was an empty wine bottle. Later in the show, Neal reveals that the empty bottle was a hidden message, which essentially meant a promise of a better life. This was ultimately why Neal did not resist being captured and arrested again, because he felt that Kate was safe, and she had intentionally left the bottle to indicate she didn't want to be followed.

While Neal tried to get Kate's attention, he performed bigger and more ambitious jobs.

Of course, as the show develops, Kate meets a fateful end, and Neal spends much of the rest of the show recovering from this incredibly challenging moment after losing the love of his life. However, it also leads to Neal getting a shot at doing investigative work alongside agent Peter Burke. Without this inciting incident, and Neal earning himself more time in custody, he was more than happy to accept a job as a consultant and get himself out of his shackles more often. But, had he not escaped prison, he could have finished his sentence and been a free man with no FBI oversight in his life, but then White Collar would lose its most compelling story.