@metalmutant: So not 100% sure but what you described sounds a lot like Cyberdogs aka Cdogs, a top down 2d shooter where you bought weapons beforehand then scrounged the level for money, equipment of varying kinds and your objectives. There was also co-op, though you had to play on the numpad which created some awkward shoulder-to-shoulder moments. I'm not 100% if the enemies were actually armed thieves necessarily or if there was a boss with any combination of the words you mentioned, but you can play as a bald guy with a mono-color jumpsuit.
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