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RE: Riddle Me This! #2: SBD Earnings go to winner on payout.
I'm thinking he's betting for the same - or higher amount with someone else, but somehow knows that whatever horse he legitimately bids on will lose... Hence whichever horse he bids on, he knows will lose, and then bids on another one with his other bookie...
Or something similar, hmm~.
I like your take on it.