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Jack studies each move his prospective "associates" makes with the focus of a master chess player. The treatment shown to the interested girl only served to increase her value to Jack, though what it meant in placement was still to be discovered.
"Why didn't your friend come?"
The former detective takes his time with his reply, sloshing the beer around his teeth all the while eyeing Ira with a confident aura of indifference.
"A strong organization has one voice. If I had her tag along, might be the wrong proposals be made or the wrong terms agreed on. I'm sure you understand." Jack, again, takes a snail's pace with his toxic intake - first beer then cigarette - allowing his listeners to digest the mixed message his answer suggested.
"I need men; not boys, not a bunch a f~&~in' idiots lookin' to cause mayhem for a laugh. Soldiers. Take orders; that means they don't do anything they aren't ordered to do. Word is: the Cassidy-Monroes are a mixed bag. Your reputation... inconsistent. My plan is simple and all I need are numbers. I guarantee whoever makes up those numbers will find themselves cozy n' powerful. Why should I give this gift to the Cassidy-Monroes?" he asks Ira with unflinching decisiveness.
Turning to Adrian with the same intensity, "What reason do I have to trust you'll carry it through?"
Persuasion (influence 'tude): 1d20 + 5 ⇒ (20) + 5 = 25
Perception (cop a crowd feel): 1d20 + 12 ⇒ (9) + 12 = 21
Just a note: his being so blunt is to show authority and leadership. This may not seem like the right sort of statement for a diplomacy check but gangs are a bit like dogs - they follow the Alpha.