Following is a sampling of the political cartoons produced as America transitioned from the self-absorptive Gilded Age to an era of grand reform championed by the Progressives. The octopus was a favorite visual metaphor used by cartoonists to convey the villanous monopolies. In late nineteenth-century America, the octopus seemed, metaphorically, to be everywhere. It was not a sea monster, but every bit as menacing as a land creature, instilled with clear rationality, malicious purpose, and unbridled appetite. Why did this image resonate so deeply within the popular imagination of the era? It was due to the growing awareness of the extent to which massive, centralized, interlocking networks of administration, organization, production, and distribution were shaping American life. Trapped in such systems, the American public suffered an infringement of autonomy in nearly every realm. While the specific local conditions to which each of these three cartoons refer are different, their message is consistent.

Perhaps the most recognized of all the octopus-imaged cartoons is that of Ashcan School artist George B. Luks, entitled "The Menace of the Hour." After years of calculated delay in construction of the New York City subway, the issue finally boiled over in early 1899. Tammany Hall politicians and the businessmen who monopolized the city's street railways were resistant to the competition that a subway system would bring. On the other hand, the public was demanding more efficient, less crowded urban transit. Outrage over the manner in which the contract was awarded, as well as terms of contract itself, caused Governor Theodore Roosevelt to intervene. The action earned him the enmity of corrupt New York City politicians and businessmen.

Standard Oil Company of Ohio, under John Davison Rockefeller, was a common target for political cartoonists of the era, such as Udo J. Keppler. His 1904 "Next!" drawing used the octopus to depict Standard Oil. Rockefeller entered the petroleum refining business in 1863 and a few years later embarked on the strategy of purchasing rival oil companies and consolidating them under one company. In a series of articles entitled "The History of the Standard Oil Company" (printed in McClure's Magazine, 1902-04), Ida Tarbell attacked the oil tycoon who had forced her father out of business, accusing Rockefeller of building his company through "hard dealing, sly tricks, [and] special privileges." It is one of the Progressive Era's most famous muckraker exposés. Later, in Standard Oil Company of New Jersey et al. v. United States (1911), the Supreme Court agreed with Tarbell.

The railroad became America's primary symbol of industrial power and continental expansion during the late 1800s, and was therefore seemingly granted carte blanche by the government. Congress backtracked somewhat when it attempted to install some degree of regulation through the Interstate Commerce Act of 1887. Political cartoonists have portrayed the railroad industry (including magnates Charles Croker, Mark Hopkins, Leland Stanford, and Cornelius Vanderbilt, to name a few) in numerous villainous forms—an octopus, Dr. Frankenstein's monster, and a giant puppeteer, to list a few. The 1901 novel The Octopus, by Frank Norris, is the best known of several muckraker attempts to expose railroad-sponsored injustices. The book presents an account of the Mussel Slough incident of 1880, a land dispute between California wheat farmers and the Southern Pacific Railroad which culminated in the deaths of eight men from both sides of the conflict.