“The End of the Circus Season” by  William Allen Rogers published November 3, 1900, in Harper’s Weekly p.1050

Democratic nominee William Jennings Bryan is pictured as a clown dejected by his impending defeat. He rides the exhausted Democratic Donkey through a driving rain storm, while carrying the symbols of his failed issues—free silver (bunco dollar), imperialism (tyrant), and antitrust (octopus). The scene evokes the literary analogy of Don Quixote, who tilted at imaginary windmills, and the body of water is probably meant to be the Salt River, a metaphor for political defeat.

Source of image and quote: Harp Week (Accessed 27th Aug 2010)

Octopus of ‘Monopoly’ by John Tenniel published in Punch, or the London Charivai, November 3rd,1888. The octopus of “Monopoly” attempts to upset the boat of oar-wielding ‘Commerce’ (wearing the winged hat of Hermes or Mercury?). The octopus’s limbs are: ’salt’, ‘iron’, ‘copper’, and ‘cotton’. The boat is called: “Free Competition” (A case of ‘bad’ versus ‘good’ capitalism?).

Image source: Fotosearch, http://www.fotosearch.com (Accessed: 16th March 2009)