thesnowleopard: your argument is reasonable, but I still think it's conjecture. In support of your view, the film is at best neutral on whether Max wants to get caught. You basically have to take a psychiatrist's perspective in explaining Max's motivations (the "all hardcore gamblers want to lose" sort of thinking), when there are simpler explanations for Max's apparent self-sabotage that are rooted in basic human nature.
Yes, we would need to go from a psychiatrist's perspective, since Max is so lacking in self-insight, he's almost constantly lying to himself and everyone around him about what he really wants and really feels. He's practically on autopilot for much of the film. So, asking Max most of the time why he's doing what he's doing is pointless. He doesn't know.
It's a large part of why he is the way he is, which is too institutionalized to survive on the outside without getting killed or caught again. Sure, he's going to fight those alternatives, but once one of them comes, he'll likely feel mostly relief.
Is he also greedy and arrogant and going hog wild with his new freedom on the outside? Sure. But are those his primary motivations for being
really stupid about his big crime spree, to the point where it's a guarantee things won't end well for him? No, those seem pretty weak to me. That final montage is not an elegy for a free spirit.
Vanishing Point is about a guy who just wants to be free, but is ultimately crushed by a cruel and unfair system. I would argue that while Straight Time initially appears to be a similar film, it ultimately turns out to be something quite different.
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