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Does it mean

  1. He doesn't have a strong will to win
  2. Gods do not decide that he should win

Bonus: How those 2 meaning of determined related? One means strong will, another means predestination.

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up vote 2 down vote accepted

It almost certainly means the first. To have the second meaning unambiguously it would have to be something like Some people are predestined not to win. But, as I have to keep saying, it all depends on the context.

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