The central problem facing most writers or directors of crime films is how to make the audience care for and about characters who do things they would not tolerate (much less approve of) from people in real life. There are several conventional ways of trying to engender sympathy for a protagonist who is a criminal. Contraband uses all of them in a mostly failed attempt to convince us that smuggler Chris Farraday—despite participating in armed robbery, sabotaging an ocean freighter (nearly causing a collision and thereby endangering the lives of scores of workers), smuggling hundreds of thousands of dollars in counterfeit currency which will be used to fund other criminal enterprises, and stealing a $40 million painting to sell on the black market—really is, at heart, a decent guy.
I was not persuaded.
The first step toward making the criminal character more palatable is underscoring that he is a reluctant criminal. When the film opens, Chris (Mark Wahlberg) has turned his back on a life of crime. His imprisoned father even says that he was never more proud than on the day Chris "turned legit." When Chris's brother-in-law, Andy, messes up a drug deal, Chris agrees to pay back the dealer who would otherwise kill Andy. Loyalty to a relative is admirable, but by accepting responsibility for the debt, Chris places his own family in jeopardy, betting the lives and welfare of his wife and kids on the success of his smuggling plan. He pays lip service to being angry at his brother-in-law, but in one telling scene of horseplay on the boat, Andy says he can tell that Chris is glad to be back in action and is not contradicted. Did Chris really have no other choices in this situation, or was the threat to Andy a justification for doing something he was inclined to do anyway?
Another way in which the criminal protagonist is often softened is that he is supposed to have a code. In this way he shows himself, while flawed, to be preferable by contrast to other criminals and thus worthy of our respect. Contraband gestures once or twice at this convention. Chris initially refuses to smuggle drugs, implying that the smuggling of counterfeit currency is somehow less insidious than smuggling the actual drugs that the money will be used to buy. More directly, while the drug dealer (Giovanni Ribisi in full-out, crazy-man mode) is willing to beat up Chris's wife and threaten his kids, Chris cuts short an assault on him when he sees the dealer's daughter is watching them. The ship's captain is shown to be corrupt on a grander scale than Chris, and Chris's loyalty is contrasted with another character's unexpected betrayal. None of that makes Chris good, though; it just makes him not as bad as the people he is stealing for.
Finally, criminal characters can sometimes engender sympathy by exercising skill in their enterprise. Even if we don't approve of the ends to which talents are put, the audience can still admire cleverness, preparation, discipline, or intelligence. As criminal geniuses go, however, Chris is no Professor Moriarity. Contraband is essentially an action movie, so it is more concerned with putting Chris in situations where he can shoot or fight his way out of a jam than in ones where he can figure things out. The one scene in which Chris has to make a deduction was so badly telegraphed that rather than making him look smart for his realization it makes him look dumb for having been fooled so long by someone not particularly bright himself.