Honestly Shanks hadn't notice how late it was getting until Luffy fell asleep against the bar. The pirate doesn't think anything of it at first, just snorts a laugh at how quickly the boy went from wide awake to fast asleep and goes back to drinking. Then as he's draining the last of the rum from his glass, he sees Luffy start slipping off the bar stool. Shanks moves without really thinking, dropping his glass and snatching Luffy up off the stool before the kid can fall. Thank goodness for quick reflexes. Both his, for preventing his young friend from cracking his head open on the floor, and Benn's for saving the glass Shanks had dropped.
Nobody else, aside from Benn and Makino, seems to have noticed the commotion, even Luffy doesn't stir in the slightest as Shanks holds him tightly to his chest. The pirate captain breathes a sigh of relief and exasperation. This kid has given him more heart attacks in six months than anything else has in his entire career as a pirate. Shanks sits back down on his bar stool, hooking one arm under Luffy's legs to leave the other free for drinking. Of course as soon as he gets settled and even resigns himself to the fact that he's gonna have a seven year old drooling on his shoulder for the rest of the night, that's when Luffy finally stirs. Shanks starts holding his breath when the kid's snoring cuts of with an abrupt snort, waiting for the inevitable indignant wails about being held like a little kid.
So he's taken entirely off guard when Luffy just rubs at his eye with one tiny hand. "Shanks?"
"Hm?" He responds a little hesitantly.
Luffy buries his face in Shanks's shirt and mumbles, sleepily, "Let me join your crew…"
With that he falls right back to sleep without even waiting for a reply. Not that he'd get one right now anyway, because Shanks is speechless. That's fucking cheating! Asking for something Shanks absolutely cannot grant while being this adorable is definitely cheating. It has to be. He kind of wonders if this is how parents feel when they have to be responsible and not let their kids do incredibly stupid and reckless things. Because if it is, Shanks is never, absolutely never, going to have kids. This is torture.
Slowly Shanks turns to Benn, putting on his best pout and just staring, helplessly at his first mate. Benn, the heartless snake, just laughs and pushes Shanks's empty glass down the bar towards Makino, who happily refills it, giggling behind her hand. As he takes the now full glass from Makino and passes it to Shanks, Benn claps the redhead on the shoulder, very gently, and says, "Stay strong, Captain."
Shanks just whines as he adjusts his hold on Luffy. Easy for him to say.