Kenyon Cox, COLUMBIA & CUBA – MAGAZINE COVER – NUDE STUDY (1898)
In an essay that appears in Race and the Production of Modern American Nationalism, Maria DeGuzman has this to say about the above image:
Besides connoting the stronger/weaker sister relationship, the drawing plays on an older/younger sister or mother/daughter relationship. It suggests a scenario in which the older sister/mother (Columbia) has just finished disciplining the younger siter/daughter (Cuba) and is standing proudly while Cuba clings contritely to Columbia who wields a big stick, paddle, or bat…. [I]mages like this one need no support from male representatives of American power because such militantly masculinized images incorporate them already. However, Columbia’s muscular, mannish are leading down to the hand which grips the phallic stick may also be interpreted as leading back to these male representatives. The club is a clear reminder of the long arm of Uncle Sam and the “big-stick policy” articulated by Theodore Roosevelt. Both the Columbia and Cuba of Cox’s study gaze out at the viewer. One might imagine that this veiwer coule be a “New Woman” herself, a suffragette for whom such an image of female power, however imperialistic, might still have had emancipatory appeal. Nonetheless, the point to which the figure’s look is directed might just as easily be Uncle Sam’s controlling gaze. Columbia’s posture is remindful of that of a soldier standing at attention before this gaze which in the cartoon is not embodied by a corresponding cartoon character, but rather transparently conscripts the viewer.
This passage, though not without insight, exemplifies something that bugs me about a lot of art criticism. As Susan Sontag explains, “The aim of all commentary on art now should be to make works of art—and, by analogy, our own experience—more, rather than less, real to us. The function of criticism should be to show how it is what it is, even that it is what it is, rather than to show what it means.” In other words, I seriously doubt most people’s first reaction to the above image is, “Of course, it’s about American imperialism. How obvious!” To quote Sontag again: “In place of a hermeneutics we need an erotics of art.”
Submitted For Your Perusal 
This allegory looks much more like a scene with Columbia as Cuba’s protector. And Roosevelt first spoke of the “big stick” in 1901.
These figures would’ve been clothed for the cover, no?
Yes, Michael, I imagine they would be clothed for the cover. Thanks for your comment.
Please note that author of the above item has incorrectly identified the author of the quoted passage. The actual author is Maria DeGuzman. The quote appears at p. 107 of her essay “Consolidating Anglo-American Imperial Identity Around the Spanish-American War (1898).” Reynolds Scott-Childress was the editor of the work.
Thank you for calling my attention to this! I have updated the post to give DeGuzman credit, as well as softened my judgment of her analysis, which I now, nine years later, find far less vexing.