The joke rightly bombed, but the reason is much more interesting than “you can’t call Puerto Rico an island of garbage because it’s amazing.” The joke bombed because the audience doesn’t have a secure enough relationship with Puerto Rico to joke about it like that. There’s a certain sort of edgy humor you could call the “older brother” joke. You know the sort: you call your brother a moron, but if anyone else does, they can meet you behind the schoolhouse. Call it negging, call it mean-funny, call it what you like—the key is that it’s rooted both in genuine affection and not in any real insecurity. How does that saying go? Women socialize by complimenting each other and not meaning it, men by insulting each other and not meaning it. Every healthy male friend group I’m in is peppered with both a constant stream of joking insults and with sincere mutual affection. There’s a great moment in Succession when one of the characters, invited to talk degradingly to her husband in pillow talk, tells him “I’m too good for you. That’s why you love me, even though I don’t love you. But you want me anyway.” And she tries to pass it off as a joke and she tries to recover from it, but on some level both of them know she actually feels that way and it ruins them. Puerto Rico and other US territories are sort of niggling awkward questions for the US. People from the Northern Mariana Islands are citizens and can vote, but how many Americans think of Saipan on a regular basis? How many of them feel in their bones that it’s The Same As Them? I haven’t been to Puerto Rico, but I did stop over in Saipan for a few days. And it was beautiful and it was fun and it was great and I’d love to go back sometime, and it was also clearly and palpably at a different stage of development to that of US states. The richest US territory, per capita, has a lower GDP than the poorest state. People in the territories are US citizens, but they live far away from the empire heartland and nobody quite has a serious plan for their incorporation as states, nobody’s quite sure what to do with them—remnants, as they are, of a different era. That can and should change. We should be thrilled to have the territories as part of America, and we should not flinch at incorporating more territories as appropriate, if more areas want to be incorporated. But it creates a hint of status insecurity—of uncertainty. You can say Puerto Ricans are amazing, and it’s true! If Puerto Rico and the US—and in particular, the Republican Party—had a secure, fully mutually confident and healthy understanding of their relationship, you could rib them on the political stage and everyone could have a good time. But they don’t, and so instead the joke landed a bit more like the accidentally honest moment in Succession: That was a joke, right? You didn’t mean that, right? You don’t actually think they’re a garbage patch, when you think about them at all? You like and respect and care about them, not only as a throwaway line when you want their vote… right?