The oversized hat of his grandfather’s, which here fits over his own hat, is a symbol used by several anti-Harrison cartoonists to suggest that Benjamin Harrison did not measure up to William Henry Harrison’s stature. Democrats lampooned the younger Harrison in the campaign song “His Grandfather’s Hat,” which insisted that it could not be filled by the short (5' 6") Republican nominee they ridiculed as “Little Ben.” Republicans responded with their own campaign ditties, “Grandfather’s Hat Fits Ben” and “The Same Old Hat,” as well as distributed hat-shaped ornaments and pins.

The suit of armor for protecting large corporations (“trusts”) associates Republicans with big business and is a visual pun on James Blaine’s nickname, the plumed knight. The octopus symbolizes the corporations’ massive size and grasping reach into every area of the economy. The metaphor derives from Henry Demarest Lloyd’s three-part exposé in The Atlantic Monthly (1881), concerning the allegedly underhanded and threatening practices of the Standard Oil trust, which he called an octopus. The term was later used by Frank Norris in his novel, The Octopus (1899), to identify the Southern Pacific Railway.

The jug of free whiskey refers to the Republican platform plank expressing preference for eliminating all internal taxes to dismantling the protective tariff system. Given the importance of the prohibitionist vote in the close elections of the era, Democrats seized upon the statement to paint Republicans as advocating the abolition of taxes on alcohol. Robert “Bob” Ingersoll was a popular Republican speaker, who had dubbed Blaine the “plumed knight” at the 1876 national convention, and one of the nation’s foremost trial lawyers, who defended federal officials implicated in the Whiskey Ring and Star Route scandals. He firmly opposed the prohibition of alcohol as contrary to personal liberty, impractical to police, and a temptation toward banning tobacco and other products.