When someone asks you who is or was the greatest Gotham crime lord who do you think of? Factor in their effect on the underworld, their effect on Batman and how well they operated.
Probably Carmine Falcone. Before Batman showed up to kick his ass, he was running the whole show. After Batman showed up, no-one's really lasted long enough or went high enough to qualify as the head honcho of Gotham's underworld.
@takeluutzen: yah but he's not really a mob boss. He isn't interested in crime as a business like Carmine or the Penguin but as a way to get to Batman.
Penguin easily...just look at what he has accomplished. He climbed his way up from the bottom of the gutter to becoming a full blown mob leader, no penny in the entire city changes without his knowledge, has vast resources and capable of getting his hands on a variety of stuff from drugs to weapons to money to high technology and even runs his own club. In the New 52, he helped drive Falcone away and actually managed to take over a Gotham's premiere crime lord without shedding too much blood. Sure he blackmails and bullies to get what he wants, but out of all of Batman's enemies, he is arguably the "cleanest" and least insane. And he actually managed to form a sort of working relationship with Batman while preventing his own incarceration. As long as he keeps a low profile and doesn't hurt people while also supplying him with information, Batman leaves him be for now, however, Penguin cleans his tracks well and prevents Batman from pinning something on him, however Batman's counting on the Penguin slipping up and once he does he'll be there to put him down once and for all. But until then, despite "running Gotham" Penguin isn't a primary target for Batman compared with the other bad guys, and so as long as Penguin isn't an immediate or major threat, Batman won't go after him. And keeping a low profile is best for business as long as Penguin is concerned. It's quite an interesting dynamic.
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