Dems tried to roast Trump by pointing out the fact that he was stealing valor from billionaires who honestly extracted value from their workers instead of ripping off creditors; this obviously failed because this only makes Trump look bad to other rich people, and to the lumpen and petty-bourgie chuds this makes Trump look more badass because the criticism promotes his carefully-curated false image as some sort of crass nouveau-riche Gatsby-like figure who got rich by gaming the system and scamming the rich liberal assholes they think are all pedophiles anyway.

The Dems also tried to roast him by painting him as if he were some sort of Manchurian candidate, a de-facto puppet of Vladimir Putin. This didn’t land despite Trump’s existing business connections with Putin because Trump was easily able to fire back against Clinton for taking Saudi money and against Biden for his son making shady deals in Ukraine. “Tu quoque” has always been Trump’s best defense, and the reason why Dems and neolibs tend not to point out more obvious criticisms that make “their faves” (Clinton, Pelosi, etc.) look just as bad or worse.

The best comebacks of the childish variety they had was “Drumpf”, “Cheeto Mussolini”, “Orange man bad”, etc. “Cheeto Mussolini” is the closest one that actually sort of works to correctly pejoratively convey Trump’s proto-fascist politics, but it was often abbreviated to “The Cheeto” and robbed of any meaningful critique. Likewise, “Drumpf” was originally formulated as a direct attack on Trump’s nouveau-riche branding but most forgot about that and it too turned into an empty signifier.

Of course the Dem leadership refused to run with any of the more puerile insults directly because they didn’t want to get their hands dirty and look too uncivil, despite the Mussolini comparison actually having some potential political weight behind it that even the CNN-watching rubes can grasp.