In all honesty, as much as I love Supernatural's flashback episodes, they rarely reveal anything particularly new or enlightening about the Winchesters these days, and "Bad Boys" wasn't much of an exception. Dean's life is made of duct tape and disappointment. Sam's is made of superglue and lies. So many lies. Even something as relatively harmless as what Dean was doing for those two random months back in 1995: LIES.
Dean summed it up best when he recalled how the story that he and Douchey Dad John told Sam was simply "the story" until it just became the story—the truth, as fabricated, endorsed, and accepted by the Winchesters. Sort of how big bro is currently forcing the "story" of Sam's survival to desperately enter the accepted Winchester truth zone as well. Good luck with that one; miiiiight want to stop being a freaking WEIRDO about things. "Everybody's fine with heading out to the Catskills?" JEEZ, DEAN, IT'S LIKE YOU WANT SAMMICH TO FIGURE IT OUT.
Don't we all, though?
Get with it, Sam, plz thnx.
So anyway, once upon a time in 1995, the Wee Dean lost the food money John left when he abandoned his children in a skeevy motel to go hunt a rugaru, and the Wee Dean decided to shoplift some PB&J. He was caught and taken to a boy's home, and when Father of the Year John Winchester got the call, he left Dean there because John's the actual worst. Also, character-wise, I'm not entirely sure that made sense, because wasn't it partially John's paranoia about ol' Yellow Eyes that made him keep his kids around even though he clearly didn't have time to not be an awful father, what with slaughtering monsters and all? Maybe I'm making that up. It's been nine seasons, yo, sometimes it's hard to remember what actually happened and what was merely discussed with fellow fans on Gchat at three in the morning.
The late, somewhat great, John Winchester has always been a hard character for me to get behind. As far as hunters go, John was among the best, and he certainly has a claim to being lumped in with the heroes on this show, but he's also one of the most flawed characters on the Supernatural roster and when we talk about how Sam and Dean couldn't have become the men they are today without him, that's a comment that could be taken both positively and negatively.
"Nobody bad touched me, burned me with their smokes, or beat me with a metal hanger—I call that a win." You guys, my jaw dropped when Dean said that. That's some textbook emotionally abused child rationalization right there. Personally, I've long held the belief that John Winchester was an abusive father... just not in the sense that we tend to default to when we think of how an abusive parent acts.
Sam and Dean have all the hallmarks of emotionally abused children, but given what we saw in "Bad Boys"—which may not have been mind-blowing, but was still pretty insightful, especially since most of the show's past flashbacks have focused primarily on Sam—Dean's in his mid-thirties and he's still struggling to come to terms with the turns that his life, and by association, Sam's life, have taken. He'll condemn John, then defend him in his next breath. Some part of Dean clearly recognizes the wrongness of the environment he was raised in and the way John acted toward him, as illustrated by the way he's interacted with children throughout the entire series—from that mute kid in "Dead in the Water" to Ben Braeden to Creepy Timmy in this week's episode. Even Dean's interactions with pre-Stanford Sam in other flashback episodes have shown a near-total rejection of the lessons taught at the John Winchester School of Horrendous Parenting.
At the same time, Dean and Sam are by no means functional, well-adjusted people (because where's the fun in that?) and one of the most telling tragedies that came to light in "Bad Boys" is that we saw how the positive lessons Dean gleaned during his time at Sonny's home have backfired due to their incompatibility with what was drilled into him from the age of four. Did anybody else cringe a little when Sonny told Dean to "Do what's best for you, even if it hurts the ones you love"? Like... maybe stuffing an angel into your unwilling brother in order to keep him alive—without his knowledge—even though he was kind of okay with not being alive anymore and we've been holding our breath for like, seven episodes waiting for the inevitable soul-crushing fallout?
Dean's compulsive need to keep Sam around stems from his own personal wants, sure, but also from a lifetime of being assigned that very task: He wasn't merely told to keep Sam safe, he was practically programmed to always, always, always put Sam first. Dean's self-worth is so tied up in whether or not Sam has a pulse that over and over and over again he's made terrible decisions with that singular goal in mind—and he'll continue to make terrible decisions because he can't help it. Dean's miserable right now, and a part of him is certainly regretting the whole Ezekiel thing, but he still can't bring himself to face the alternative.
Teen Dean came close, though. He said he wanted to be a mechanic because after you fix the cars and they drive away, they aren't your problem anymore. Dude was so not just talking about cars. Perhaps—and this is just my face making words that may or may not make sense—in some small way that Dean will deny forever, Sam running off to Stanford when he was 18 wasn't actually the worst thing that ever happened to Dean.
Anyway, of course John came to fetch Dean before the big high school dance. Of course he did. Life-ruiner. But hey, at least Dean's teenage crush is still alive. And human. (Sorry, Sam.)
Even though it largely just confirmed an awful lot of what we already knew—that even happy Winchester memories are actually fraught with emotional compromise—"Bad Boys" also, finally, gave us an honest look at what makes Dean Winchester tick. It may not be pretty, and to call it "noble" is to severely misunderstand how emotional abuse and manipulation works, but it is completely human and understandable, and when Dean makes his unfortunate life choices and we all go "WTF ARE YOU THINKING?" I believe that now, we all know exactly what Dean's thinking.
OMG I'm gonna cry again. #help
– Teen Dean got good grades and made the wrestling team and I can't... stop... crying. The werewolf bruises also really broke my feels.
– So Sonny taught Dean how to get out of handcuffs with a paperclip, eh? Aww.
– Welp, I'm never showering again. THAT WAS SO AWESOME AND NOT OKAY. I was expecting more gore with the lawnmower, though. I mean, it was a lawnmower.
– For a second, the fiancé and I thought Sonny was played by Josh Brolin too... but it's actually Blake Gibbons from a bunch of stuff, including General Hospital. Love the 'stache!