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If he didn't specify that if you won already you can't win again then yea i believe you were wronged.
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In regards to that, he said in the first bush race (that nanners won I believe) that if someone wins who owns the top hat, he can't reward you a different hat, no explanation as to why though.
So apart from that if you won the dodge as well then maybe you can't win 2 in a row? I'm not sure, if that was the case he probably should've told you that