Break SHA256, and you can cause hash collisions that allows you to easily mine blocks until 51% of the network switches to a better hashing algorithm (which should happen pretty quick, because it'll be obvious that someone broke it). To steal users money, you'd have to break ECDSA.
Edit: I wasn't 100% exact. It gives you more [1] than easily mining blocks, but still not that much power so that I would call it "Winning".
[1] https://en.bitcoin.it/wiki/Weaknesses#Attacker_has_a_lot_of_...