As big a whale as DSP is, I'd bet it's nearly impossible for him to lose either.
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I'm willing to bet that DSP wins 99%+ of his battles, and I'm not exaggerating that number. He MIGHT lose 1 or 2 battles per week if he gets a really bad loadout, but with trainers and stuff these guys start with their finishers already powered up. Also, a lot of their finishers are stuff like "create 8 new blue blocks" so that they have combos where they hit their moves AND power up their moves for the next turn.