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I'm stuck, I  can't get the Outsiders first Lt to show up at all. The bar is showing I've maxed rank 2 with them but nothing else has happened, is there something I'm missing?

Same happened for me. No idea if I did something wrong but I think it's a bug.

same I got the same proble.

Yes, you forgot that you have to rise your own army of mind-controlled agents then attack the gangs during land grabs in order to push gang leaders to show themselves. 😉