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I had seen this 1899 political cartoon about the USA's new colonial empire many times, but only in smaller scans where the whiteboard and other small text could not be read.
This caricature was made by Louis Dalrymple (1866-1905) and appeared on the Jan. 25, 1899 of Puck, a humoristic, satirical magazine. Which raises the question as to how earnest the portrayal is. I don't know the answer, but it sure hasn't aged well.
1898 Dalrymple caricature (also in Puck), on Cuba and the Spanish-American War. "The duty of the hour:—To save her not only from Spain but from a worse fate."
The banners that two armies flanking the "Anarchy" fire carry are labeled "Insurgents" and "Autonomists."
Flag nerds will note that the Cuban flag is depicted with light blue stripes, and ponder its significance. The very earliest Cuban flags (from c. 1850) were dark blue stripes.
Here's a 1903 Dalrymple titled "The unrestricted dumping-ground." Yikes. The man in the thought bubble is President McKinley, who'd been assassinated a couple years before by Polish-American anarchist Leon Czolgosz (US born).
"Our Christmas Tree," Dec. 1899 cartoon in Puck by Joseph Keppler. When this was published people in Puerto Rico had been dying in the thousands from the aftermath of hurricane San Ciriaco.
Keppler, in Puck, 1901. "Encouraging the Child." Uncle Sam tells Cuba, who is playing with a model Capitol building that says "Cuban Independence": "That's right, my boy! Go ahead! But remember, I'll always keep a Father's eye on you!"
Another political humor magazine of the time that seems relevant was called Judge. Here's the Feb. 3, 1906 cover.
McKinley vs. William Jennings Bryan, 1900 election. "Do you want a man who, having raised the stars and stripes on our new possessions, will maintain them with dignity; or a man who will cut down 'Old Glory' and make us the laughing-stock of the world?" (Signed Victor Gillam.)
UNCLE SAM. — "Gosh! I wish they wouldn't come quite so many in a bunch; but if I've got to take them, I guess I can do as well by them as I've done by the others!" Signed Keppler; in Puck, Aug. 3 1898.
