Another problem with The New Yorker's cartoon-caption contest:
Gordon Baumbacher's caption is actually pretty funny, BUT...it just plum doesn't work. For it to make any sense, you have to ignore the smiles on the mobsters' faces. Why are they all smiling? Sure, you could say they're being ironic or sardonic or something like that, but if that's true, then it complicates and undermines the joke, mucks it up—and besides, that's obviously not really the idea. The idea is, "Let's pretend they're not smiling: then it works great!"
That's really all I had to say, but let's just note that the second and third entries are classic caption-contest fare: lame "topical" humor. Wilcox's at least resembles humor, but it, like Baumbacher's (but more so), doesn't actually make sense.
[I feel a little bad trashing random citizens' attempts at humor. Let me just state here plainly that I hate the game, not the player. And let me say, too, unrelatedly, that this week's New Yorker has a George Saunders story in it—and I haven't read it, yet, but yay George Saunders!]