I believe he means literally people in prison but with enough power and influence to continue to manage operations from within.

Aye, the statement was many on the inside to one on the outside, yeah? =] For the "kingpin" scenario, it would be many on the outside to one on the inside, right?

(Admittedly, I may be misunderstanding, which is why I'm asking.)

Here is one example but the reply is also correct.

https://amp.businessinsider.com/mexican-drug-lord-el-chapo-b...

I'm probably misunderstanding but that would be many on the outside speaking to one on the inside, yeah?