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Joining us today is Race Across America 8 time. The first trip to the winner's circle for Caldwell came in the Xfinity race — he's won both series races he's entered this. Racers will receive a Strider jersey, number plate for their bike and a goodie bag valued at more than $50. So do your World Champs wins mean more to you than say a championship overall win? The other closely watched race where Trump was campaigning for Balderson the.