It's an interesting glimpse into Break's old life -- into who he was, beyond the relatable things they share. The monster hunting, the kids to watch out for. Qrow certainly knows stuffy people who are invaluable to have at your side in a crisis, but he wouldn't say he's particularly close to either of the two that come to mind straight away. Glynda was his senior colleague, ultimately, connected mutually through Ozpin. And Winter...well, Winter was Atlesian. It always had been complicated.

Qrow, meanwhile--ah, it's like he said to Clover, back when. He's found that working alone tends to be for the best.

"Ugh, paperwork. Pretty sure I had a colleague who would've done that to me if I couldn't just fly away."

He is sure this has caused Glynda no end of aggravation, but in fairness, that was also Ozpin's doing, so. It evens out!!! Or something.

"You'd think with all the time they spend nagging us to do it, they could get it done already, right?"

Who needs bureaucracy, quoth the ex-forest vagrant.

"He sounds like a solid guy, though. Glad you've got someone like that watching out for your kids."

Qrow doesn't say that there would be a version of him taking care of things back there even if he were to wash up in Trench; from their past talks, he doesn't think it would be a particularly comforting sentiment to hear, especially from someone who's chosen to leave his old life behind at this point.