Having another hunter around, Michael and the gang have managed to get a rhythm going. One that includes Dean getting to eat, sleep, and even have some one-on-one time with his family.
This is one of those one-on-one's.

"Checkmate."

"What?" Sam asked with a disbelieving chuckle.

"Checkmate, dude."

"Uh, look again, dude: my king's safe and I've still got-"

"You look again, dude, 'cause your king's one move away from gettin' his freakin' head cut off."

Sam looked up from the admittedly close game to better argue his side, but at the unexpected sight of a serious, studious expression across from him, instead found himself swallowing whatever he'd been about to say. Mouth snapping shut when Dean caught him staring.

"Don't look at me," the older Winchester said with a sudden, widening smirk, "it's your king needs help."

Deciding to humor the guy who hadn't had so much as half a chance for cheating in the completely distraction free solitude of his Room, Sam looked back down to where his king was sitting safe and sound exactly where he'd left it. On the outskirts of an active war zone, snuggled between just enough protective heavy hitters to-

"Wait, when did your knight get there?" Sam demanded, leaning to squint himself a better look at the board in the 'light' provided by their wimpy, half used candle. Nearly balking at how close to death it turned out his principal piece actually was.

"Told ya," Dean said with a cocky snort.

Not sure exactly what'd just happened, Sam snapped his head back up to figure it out. Only, when he met eyes with his opponent, it wasn't the pair of eyes he'd been expecting to find in that smug face.

"For once, your ignoramos of an older brother is right," the uninvited archangel informed with a prim nod. "Checkmate."

"Hey, my brother's not an ignoramos," Sam all but snapped as-

"Okay. Where'd that come from?"

As Michael let Dean back out. Without even the hint of a warning.

"Uh... Sorry?" Sam saved, surprised that Michael was still able to do that without Dean noticing. "What I meant was: The student becomes the teacher. Good game," Sam said, holding out his hand for a congratulatory shake. Remembering late that that was one of Dean's big 'visiting the guy possessed by an archangel' no-no's.

Thankfully, the victor pretended he hadn't seen the thoughtless gesture and went straight to enjoying his spoils.
"Tch," he scoffed as he looked over the board, no doubt counting how many of Sam's pieces he'd managed to capture, "dude, I've been letting you win since you were, like, nine."

"What?"

"Figured you were old enough now I could stop holding back," the guy in the clunky handcuffs said as he eased his hands behind his head and took a leisurely lean back in his bright red, childproof beanbag. Self-satisfied look deepening with every moment the younger brother spent wracking his memory for a sign- any sign that might prove the assertion one way or the other.

After what felt like far too long, Sam straightened, ignoring the shift of polystyrene pellets beneath his own tuchus, stared his brother right in the eye and went with his gut.
"Bullshit."

The only answer it got him was a cackling laugh the likes of which Sam hadn't heard since... probably back before the two of them had brought about Armageddon. The first time. Back before Dean had finally gotten out of the juvenile habit of making fun of Sam every time he made even the slightest slip up.
This laugh though wasn't quite as 'you're an idiot' as those had been, and honestly, Sam was glad Dean had it in him to let loose a little. In fact, considering everything, he wasn't going to hold it against Dean even if the guy was blowing one hundred percent, grade A smoke up his a-

"Naw, Sam, I mean, you're great and all, it's just-" Dean cut himself off while he made a face that looked like him trying and failing to wipe away his victorious grin. Then he started over.
"You know those books you made me check out for you so you could become 'a chess playing grandmaster'? That summer, way back?"

"I don't remember saying it like that, but yeah?" Sam acknowledged, completely at a loss as to where this was going. And where it was coming from.

With a Cheshire grin the size of which Sam hadn't seen in ages, Dean eventually answered.
"I read them first."

Sam felt his mind short circuit at the distant memory of his extremely younger self pestering a similarly younger Dean over when he was going to get to read the new book he'd asked his big bro to bring home with him.
"'I'll give it to you when I'm good and ready.' Oh my God. I thought you were just being a jerk; sitting on it- making me beg and do chores while-while you watched tv on the couch. But you were actually reading them?"

"If I didn't know how to play, you'd've been bored out of your skull before we got the board set up," Dean confirmed with a sagely nod. Smile turned soft the way it always did when he talked about 'the good old days'.

"Wait, if you knew how to play, then why'd you make me explain the rules every time we broke it out?" Sam asked, unable to curb his curiosity.

"Nothing nine year old you enjoyed better than getting to tell people what to do," came the most ridiculous answer Sam'd- "'Sides, made the games last longer."

To that, Sam could only sit back and stare. Stare at the brother who never ceased to annoy, stump, and —it turned out— care about him. Which made Sam wonder with a thick, sickly sinking feeling, somewhere deep in his gut, just how much of what Dean used to do- or even still did, was for his 'little' brother's benefit?

In response to the lengthening silence, Dean shook his head and began straightening the board.
"Well, I know you got important Apocalypse Gang coordinating stuff to get back to, so-"

"Actually, Cas is on top of that today," Sam corrected, "So, you're not getting rid of me that easy."

"...You givin' me permission to kick your ass?" Dean ventured. The shimmer of their momentarily guttering candle playing tricks with Sam's eyes, making it look almost like the guy across from him was second guessing his own question.

"Giving you permission to try," Sam corrected.

"Well, alright then. Guess Sammy the grandmaster's finally gonna see what playing in the big leagues feels like," Dean said, a hint of challenge sneaking into it near the end.

Sam smiled at that. Couldn't help it. Wasn't gonna let himself ignore the new evidence to suggest that, no matter how aloof he might've acted at the time, Dean had always cared. And that even back then, even at his teenaged jerkiest, he'd been way better at showing it than their dad ever had.

Bolstered by the eagerness in Dean's movements as he reset the board, Sam regrouped and put his full attention on the game that was about to start. Hoping to beat the guy who'd just made one of the loftiest claims a chess player could make.

But as he reached out and made his first move, Sam found himself once again staring at that studious expression across from him. The one that looked so very out of place on that ultimately familiar face.
It was in that moment that Sam realized that somewhere in the recesses of his psyche, somewhere where a young version of himself still held onto that flame of hero worship he'd once held so tight to, that he wanted his big bro to make good on that ridiculous threat of his. That the little kid in him wanted Dean to win.

That Sam wanted his big brother to prove just how good he was and kick his kid brother's ass.
Royally

I've only ever played a few games of it, so please bear with me if the depiction of chess in this chapter is at all wonky!
Also, I figured that this would be the kind of thing Dean would do for his little bro. So I went to town and made him a chess playing virtuoso! XD
Hope y'all enjoyed the brotherly bonding!