What Sullivan likely did not foresee was that Trump would drive so many others crazy that he could return to a less demanding column while appearing almost as a voice of reason. He could not possibly have foreseen someone like Louise Mensch claiming that a sealed indictment had already been filed against Trump in May 2017. Or that a Mike Cernovich would portray then-National Security Adviser H.R. McMaster as a puppet of the Rothschilds. Or that so many between those poles would loosen their moorings.
To be sure, Sullivan remains hyperbolic. His inaugural column for New York in May 2016 argued America has never been so prone to tyranny (that he recycled it in March 2018 might be considered somewhat self-refuting).
But unlike his contemporaries at The Atlantic, Vox, and The New Republic, the heart of his argument was that we reached late-stage democracy because a century of progressive activism eroded the republican safeguards built into our Constitution by the Founders and the historical elitism of institutions like our political parties.