Before entering politics, Rogers worked for a sports handicapping service, using the name “Will 'The Winner' Rogers”. He encouraged bettors to dial a "pay-per-call number" and claimed to have an 80% success rate for his predictions. A CEO of a sports pick firm said Rogers was in the “kind of seedy end of the industry.” and "If that’s the biggest skeleton he has in his closet, I say elect him president of the United States.” [6] Rogers said the media stories on the topic were "gutter politics"; he said the work was scripted, and that he was not a sports handicapper.[7][8] The sports pick firm CEO said that Rogers' claim that he was simply paid to read a script was "stretching the truth. But I know where he’s been as far as not having total editorial control of your content."[6]
Rogers and Tom Graves were sued by Bartow County Bank for a defaulted $2.2 million loan on the Oglethorpe Inn, They had transferred ownership of the hotel to John Edens, but remained as guarantors for the loan. Rogers and Graves settled the matter out of court, with the bank reducing the value of their guaranty to $1.2 million. The Bartow County Bank's former chairman said their acts "contributed significantly" to his bank's eventual failure.[9]
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