The Bryang Kayo story is pretty interesting too - he was part of a loaded, underachieving U17 team from a couple years back. He's a DC United academy player, but wants to go overseas. While I don't think I've ever heard specifics, he elects not to sign with DC, and instead signs with Orange County of the USL. Never plays for them, but then signed with Wolfsburg when we turned 18.
There's some sketchy stuff happening - by not signing with DC, they aren't entitled to youth compensation. While I'm sure Orange County got something for being the middle man, its not great that players are circumventing the process to get where they want and teams aren't getting compensated. I don't blame the players, MLS needs to change things.
Caden Clark is another one - RB Leipzig wants to sign him, but he can't until he's 18. Not a MLS academy player, but wants to play professionally until then. But, if he signs with MLS, he loses a ton of leverage in making that move happen. So instead, he signed with NYRB 2 team (also in USL). He's know basically in the funnel of RBL without any compensation to any youth teams.