Corrected entry: Willie has a criminal record and has been in prison. We know this from his intro commentary. But throughout the movie he leaves his fingerprints everywhere, most notably early on when he steals a car and leaves car keys all over the parking lot and then proceeds to crack the safe in the hose without gloves. It would seem very unlikely that he has remained at liberty for his seven years of safe cracking.
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Correction: Willie is a small time thief that travels from town to town. His Santa gig is perfect in that hardly any background checks are done for applicants. Not to mention that he only does it once a year. So despite his leaving fingerprints, police would probably not have a current address and would not be very concerned with trying to catch him (as opposed to say an armed bank robber.) However unlikely it may seem, it is not impossible to go under the radar from the police for seven years.
Damian Torres