We were able to track down the original post, “The USA isn’t by any means perfect but…,” shared to r/libertarianmemes on August 3 2020 by u/Libertarian-Blade:
Later versions of the meme (including a purported correction to its labeling) became more common after the thread appeared. Originally, top text read “why socialism sucks,” and bottom text labeled the image on the left “USA” and the right “USSR.” (The USSR was dissolved in 1991.)
In the more popular version with comments appended, u/BoogiSooki commented: “The first pic is Cuba, second is Detroit.” In response, the submitted u/Libertarian-Blade replied: “wait seriously?”
That particular exchange appeared to have been deleted from the thread, but one account pointed to an August 3 2020 post to r/sendinthetanks, presumably post just prior to the meme’s emergence on r/libertarianmemes:
Of further note was that the submitter on the r/sendinthetanks’ post was u/Bolshevik-Blade — a username template matching that of u/Libertarian-Blade. Moreover, u/Libertarian-Blade’s account was created on August 3 2020, the same day u/Bolshevik-Blade indicated they intended to share the meme “to capitalist subreddits.”
As for the image on the left labeled “USSR,” it indeed showed the abandoned Packard Plant in Detroit around 2009. The image on the right (labeled “USA” and purportedly showing Cuba) appeared to primarily exist in AirBnb listings for Havana, Cuba.
Although the “why socialism sucks” meme featuring Cuba and Detroit was indeed accurately described in the comment aspect of the meme, the original thread included important context that somewhat undid the joke. On August 3 2020, Reddit user Bolshevik-Blade shared it to r/sendinthetanks with a stated intent to use the meme to mock “capitalist subreddits.” That same day, newly-minted u/Libertarian-Blade shared the image to r/libertarianmemes — where they were quickly corrected. Therefore, we have rated the claim (and what appears to be a rather clumsy attempt at a troll) Decontextualized.