In contrast, here's Mr. Warmth himself, Don Rickles. This is a long compilation, so watch as much as you want, but in the modern, politically correct era, I am supposed to say some shit like "trigger warning" or something because Rickles made a lot of racist and ethnic jokes. He got away with it because he was Don Rickles. Don't try this unless you, too, are Don Rickles. (Also, this was decades ago).
I don't even know where to start here, so I won't. Don Rickles. Rest in the grave you dug for yourself. Rather than try to unpack all of that, how about this? Here's a more brief gem from some writers who clearly learned a lot from Mr. Warmth: Matt Stone and Trey Parker.
Rather than calling someone a "loser," how about calling someone a "shit-faced cockmaster?" Or, a "donkey-raping shit-eater?" Maybe a "boner-biting bastard?" Nice alliteration there, by the way, and that's before we get into the fun of using "unclefucker" rather than simply "motherfucker."*
A Don Rickles routine, or even the juvenile-yet-hilarious name-calling from "Asses of Fire" deviates from basic, generic insults in that it shows thought. That is precisely what Trump never does. He has a few stock insults to which he always returns. Loser. Third-rate. Those are his favorites. Beyond that, he insults women's appearances, and so forth, but he just never shows any thought or creativity.
And there is some interesting history here. Years ago, Barack Obama referred to ISIS as the "JV team" of terrorism. Now, I'm not a sports guy, but whoever that team is, they'd probably still be able to beat me up, particularly after I call them "donkey-raping shit-eaters." Apparently, though, this is a diminishing comment, and Obama was attacked for having made it. Yet, to call ISIS "losers" is similarly diminishing.
Another way to diminish them might, in principle, be to show the effort of intellectual engagement with other adversaries, in the form of witty barbs, and not bother with ISIS because they aren't worth the effort. So, unload a brutal tirade of devastating verbiage towards Kim Jong Un, while not bothering with the effort for ISIS, and just call them "losers" because they don't deserve the mental effort of the tirade.
You see the problem. If everyone you don't like is a "loser," that model has no predictive power, in social science terms. See? I'm using social science! Fuck, yeah!
This, then, is the basic problem of the Trump insult. It is always the same. My advice to Trump: hire a good writer.
*Fun note as I write this: the spell-checker built into the browser/blog-editor/thingamajig doesn't object to "motherfucker" because "motherfucker" is a known word. It does object to "unclefucker." It also objects to "cockmaster." I am not particularly surprised by either, but it is interesting to point these out, particularly since English is constructed similarly to German, based around compound words. George Carlin once did an extended follow-up to the 7-words bit, on whether or not "motherfucker" belonged on the list if "fuck" was also on the list. This is turning into a longer note than I expected... Go watch a shit-load of George Carlin.