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Here Coolidge depicts the ending to the saga presented in A Bold Bluff. The bull dog did not call the Saint Bernard’s keen bluff and his pair of deuces won because the other dog folded with at least a pair of jacks. The Saint Bernard has dropped his cigar and is using both paws to collect his big winnings. All the other dogs bark in disgust after seeing the Saint Bernard’s cards, spilling a glass of scotch in the process.
Two versions of this painting exist. They are very similar but have some unique differences. One adds a poodle bringing the boys drinks and the dog’s facial expressions are slightly different in each. In fact, the multiple versions of Waterloo have been misinterpreted to be distinct ideas in the story line played out in A Bold Bluff and this painting. Only two paintings are used to depict this tail though, not three. The reason for the different paintings is not clear, although it is believed that the one with the poodle carrying drinks is Coolidge’s original idea, which Brown and Bigelow modified for their needs producing the other version. The exact circumstances are sketchy though. Other changes forced upon the artist were the title, as Coolidge originally called this painting Judge St. Bernard Wins on a Bluff
It was painted sometime before February of 1909.