The real question is: Is it still possible to be an outlaw in the 21st century? If you judge an era by the stature of its bandits, ours seems to come up short. The likes of Madoff, FARC kidnappers, pirates in the Seychelles, or Al-Qaeda terrorists don’t inspire anyone; their blind violence or shady embezzlements reek of cowardice. The new outlaws in the fields of finance and I.T., preoccupied solely with amassing their own wealth, attack both the rich and the poor without any panache to speak of, nor with any pretense of honor. All generosity has disappeared, and our world is ailing from the lack of big-hearted outlaws.
I'm fascinated by this question, and have been for a long time. The possibility for large-scale crimes of every variety is larger than it's been at any other point of history. There's more wealth, and more ways to steal, divert, transport, and misuse it. Our weapons are more lethal than they've ever been. The internet makes it possible to recruit people to causes, to deceive them, and to rip them off, in ways that would have been heretofore impossible. But perhaps because of that ease, crime seems less daring--or murderous beyond the point of glamor. There's an enormous difference between John Dillinger and Mohammed Atta. And there should be.
But I also wonder, if at a time when more people are more free and more prosperous than at almost any other time, if we're less likely to find champions in outlaws, and more likely to see them as a threat. Bernie Madoff isn't some champions of the under classes--he's a prosperous guy who stole out of greed. The recession hasn't produced outlaw champions, perhaps because folks who have been devastated by mortgages they couldn't afford, or retirement accounts that were wiped out, don't want to perceive themselves as having been plunged into a permanent underclass--they want to believe that they're going to recover their economic status, so it doesn't make sense for them to identify with criminals who are rebelling against a system many people see as rotten. Even some of the pop culture rebels who have gained large audiences in recent years are outlaws of a counterintuitive kind: Jason Bourne isn't rebelling against the state or the economic order, he's an outlaw because the government program he worked for was corrupted and went wrong. If the system functioned properly, he wouldn't be an outlaw at all.
Really, Omar Little is the only genuine rogue I can think of to have captured the popular cultural imagination in a long time, and even then, The Wire's reach isn't that enormous (sadly):
His declaration to Levy in court that, "I got the shotgun, you got the briefcase," is a textbook definition of outlawry. But for that definition to work, some people have to be getting more with briefcases than other people are getting with guns. Some people have to be willing to pick guns. And of those people, a tiny minority have to be able to making picking up that gun an act of style and defiance, both against the folks with the briefcases, and against the possibility of not making it. Not many can. These are shrunken days--the heroes are getting smaller, too.