The thought of Desmond, no matter the timeline he gets punted to, accidentally adopting a pack of feral street urchins that just think he is the coolest big bro ever makes me very happy.
Like, he remembers being young, without a home, and terrified, and most of these kids are even younger than he was.
So he starts by giving them some coin or food here and there, then he just starts teaching them how to properly pickpocket, how to climb, how to fight, and before he knows it, he has this little squad that follows after him like little chicks.
He doesn't realize it until someone else points out that he is acting very much like a mentor would.
Desmond: "Huh? Nah, I'm just making sure they survive past puberty. Maaaybe 16. Then they are on their own."
(He says, absolutely lying to himself)