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Once Upon a Time

Once Upon a Time’s Neal Cassady vs. White Collar’s Neal Caffrey — Why They’re More Similar Than You Think

Fans are divided when it comes to Neal Cassady (Michael Raymond-James) on Once Upon a Time. On one hand, he’s the kind of scruffy leading man that was desperately missing from OUAT band of merry men — we love you Charming, but you’re a little vanilla this season — but on the other, he’s kind of a jerk.

Seriously! He turned pregnant Emma into the police for a crime they both committed. Not cool, bro. (We know he did it so she could fulfill her destiny, but it was still a major party foul.) However, no matter how much of a jerk Neal was in his past, we can’t help but love his sexy smirks and wisecracking ways. Sorry Prince Charming, but some girls just love bad guys.

In fact, Cassady isn’t the first Neal to make us feel such conflicting emotions. Our other favorite Neal on TV — White Collar’s Neal Caffrey (Matt Bomer) — has a similarly disarming smirk and also happens to have a decorated past as a con artist. So how do these two Neals stack up against one another? Let’s take a look at some of their similarities.

Their Jobs

Both Neals have a knack for theft. However, while Cassady settles for small-town crime (lifting watches, stealing cars), Caffrey sets his sights on white-collar crime (conning rich people, stealing hidden treasure, etc). Needless to say, both Neals are broke and do what they need to get by.

However, when it comes to the art of conning, Cassady and his small heists can’t really compete with Caffrey, who has effortlessly made a living out of stealing rich people’s money (Robin Hood, is that you?!).

Daddy Issues

When it comes to family, both Neals have major daddy issues. Cassady didn’t have the easiest childhood. For starters, he was born in Fairytale Land, where he went by the name Baelfire. His mother, Milah, ran away with Captain Hook when life in the shire got too dull for her liking, and his dad, Rumplestiltskin, slayed “The Dark One” to keep Bae safe. Unfortunately, this meant Rumple inherited “The Dark One’s” powers. When Bae tried to help his dad rid himself of magic, Rumple backed out of the plan at the last minute. Needless to say, Bae was not impressed. Angry and upset, he ran away to the “Land Without Magic” and became Neal. Of course, the pain of his father’s betrayal never quite went away.

Caffrey, on the other hand, grew up thinking his father was dead. As Danny (because like Neal/Bae, Caffrey also has two names), he grew up believing his father was a hero and died taking out a gang of criminals. Because of this, Danny wanted to become exactly like his father. However, when he turned 18, his dad’s partner, Ellen, told him the truth, as well as the fact that his real name was Neal, not Danny. This resulted in Danny denouncing his father's surname, changing his name back to Neal, and adopting his mother's maiden name, Caffrey.

In Season 4, Neal attempts to learn more about his dad by tracking down Ellen. Before her death, she tells Neal to meet with Sam, a no-holds-barred ex-cop who knows about Neal’s father. Why? Oh, because Sam is Neal’s father! And he goes by the name James Bennett. It turns out James never died and the whole story was just a cover-up for an investigation.

So both Neals feel betrayed by their fathers, and coincidentally enough, both are now reunited with their dear old dads, which will hopefully make for some awkwardly heartwarming father-son moments in the near future. For two characters who grew up searching for some normal sense of family, it’s nice to see them both reunited with their dads. (Oh, and did we mention both of their dads are played by badass screen legends? Robert Carlyle and Treat Williams for all of the Emmys.)

Love Life

If there’s one thing Neal Caffrey has going for him (aside from his good looks and incredible physique), it’s his charm. Women just can’t resist him — and really, who could? — but that doesn’t mean that when it comes to relationships that he has the best luck. His first real love interest, Kate, a fellow con artist, died in a plane bombing. And his second lady love, Sara, totally friendzones him in Season 4. Tough break, Caffrey.

But it’s not like Cassady is doing much better in the love department. As we’ve previously noted, things between Neal and Emma are shaky, to say the least. Sure, she was the Bonnie to his Clyde before he ratted her out to the police. (We know he needed to do it so that Emma could break the curse, but that doesn’t mean we have to agree with Neal’s decision.) And if he really loved Emma, why would he fall in love with Tamara, who happens to be a total fairy-tale- character-killing psycho? He says he “needs” her, but we just don’t trust Tamara. (Sorry ‘bout it, Neal.)


As any White Collar fan knows, Caffrey has an affinity for hats, specifically fedoras, and well-tailored suits. They’re kind of like his go-to fashion accessories. In fact, why is Justin Timberlake’s “Suit & Tie” not playing every time Neal Caffrey walks onto our screens? (TV gods, make it happen!)

 photo matt-bomer-fedora_zpsade4fd82.gif

As for Cassady? Well, he’s a little bit on the scruffy, bro side. He prefers T-shirts and jeans, but he does tend to spice up his everyman ensembles with a trendy scarf every now and then. We approve.

So there you have it. It turns out these two Neals have more in common that you might have originally thought. Maybe these two could meet up in some TV character limbo and start their own spinoff? Neal and Neal: Conning for Love. Or how aboutHow to Deal With My Daddy Issues.

04.12.2013 / 11:00 PM EDT by Crystal Bell
Related: Once Upon a Time, TV Stars, Neal Cassady, Michael Raymond-James

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