What figures could fit this theme? Quickly looking over my figs, the ones that immediately come to mind are Purple Man, Mr. Fixit and Scourge.

Then, there is the Kingpin and the Red Hood. Both are good gangster types.

the punisher would be a good one

well punisher has the look but he would most likly be the one that is taking on the mafia

Cosmic Justice Lex Luthor
Legacy Blockbuster

Collateral Damage Black Mask
Unleashed Two-Face
Unleashed Mr. Bones

Patch actually makes a pretty decent enforcer type. And I think the Ultimate Nick Fury could fit in at a stretch if you wanted to stretch into a bigger-point game. But my favorite gangsters by far are the abovementioned Mr. Fixit, Mr. Bones, and the vet Legacy Joker and the Scourge. Those four will scare the bejeezus out of you just standing across the map, ready to break kneecaps.

The Hypertime Joker has a pretty good look, too. And don't forget the Penguin, if you're just looking for guys in snappy suits. At least if you repaint his godawful white jacket and pants and black with a nice blue hat.

If you're going for look, mayhaps Blockbuster?

I got nothin'. Sorry.

When he debuts, Titan from Invincible will fit into this theme quite nicely...