I say that the concept of playing a criminal is entirely off-mark without the law to keep them in check. Good cannot exist without evil in concept, and thus, crime/criminals cannot exist without law/lawpersons (I collect my PC points)
I, if I were GMing, would not shy from checking a criminal player with anything ranging from IT information security, to patrol cops, to ATF task force investigations. There is no such thing as a criminal who does not need to be careful, and there is no such thing as a criminal with no need to cover their tracks.
As a GM, I would require rolls when conducting criminal business. Diplomacy for schmoozing the drug/gun buyers, law to know what the laws are, larceny rolls to determine success/failure. Their collective failures, successes, and gray-area decisions would be kept an eye on. A string of successes means the fine life. A string of fuckups might mean safe houses and fake passports.
If the player chose to continue to roleplay the character as brazen and careless despite warnings of an incoming ATF task force, then he/she may very well drive right into a choke point and plenty of kevlar-covered officers yelling at the character to get their hands up.
At that point, the player would have a decision to make:
- Give up, but this could render the character in jail/out of reach, but I would still allow for an attempt or so to get free (jailbreak, Rodney Lawyerstein)
- Drive. Drive. Drive. Run. Hide.
- Go Tony Montana and brave a highly risky shootout that could result in death.
However the pelican chooses to fly is up to the player, but as a fair GM, I would never let a criminal character just assume a stance of "so good that it's all about the funtime to of being a criminal without any pesky law enforcement trying to squick my fun"