For most of his life, B.H. Anderson was known as the general secretary of the Butler, Pennsylvania, Chamber of Commerce, and as a page at the United States House of Representatives. After the election of Woodrow Wilson on November 5, 1912, however, he became known simply as “the man who lost his bet.” Feeling confident about Progressive Party candidate Theodore Roosevelt, he wagered with a friend that Roosevelt would be elected a third time. The terms of the bet were clear: Should Roosevelt win, his friend would walk in shame across the country with the symbol of the Republican Party — an elephant. If Wilson triumphed, Anderson would go on the same journey, but with Jasper, the “Democratic Donkey.”

The results came in — Wilson in a landslide — and Anderson grabbed Jasper, slapped a Roosevelt campaign poster on him, and took a photo on the corner of Exchange Street and Fore Street in Portland, Maine, to mark the beginning of his eight-month, 4,500-mile trek to Portland, Oregon. Along the way, he called every governor in each state he traveled through, and even made a visit to the White House to congratulate President Wilson on his win. Jasper became the first donkey ever received at the White House. Speaking of his journey, Anderson said, “Presidents, ex-presidents, governors, mayors, and all other officials seem to see the funny side of this thing. While I am glad to add to their cheerfulness, I, myself, fail to see the funny side.” — Will Bleakley

Image Library of Congress, Prints & Photographs Division, [reproduction number  LC-DIG-ggbain-12565]