Something "The Wire" pounded into our heads for sure.

Or could you be thinking of Stinky Peterson?? XD

"Roach" reminded me a lot of Cricket for some reason.

Yeah I think you're right, just rewatched it. Kind of too low-key an appearance for what would be an important person.

And I'm pretty sure the old lady mentioned in your first stray observation is supposed to be the owner of the Dolphins or at least part of the ownership team. Basically inferred from the back in the day conversation with the Rock and the diamonds and dolphins earrings.

Sounds about right. But they were doves in the pie not street pigeons.