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Starting in the present, Trump is perceived by the left as illegitimate for two reasons. First, they believe—regardless of the conclusions of official investigations—that Trump was aided by Russian malefactors in his ascent to the White House. They regard, therefore, his actions as inherently treasonous and the election of 2016 as null. Second, they categorically cannot process the fact that someone they so intensely find repulsive occupies the highest political office in the United States. It cannot compute and so at some deep level must not be possible for such an object of their disgust to in any way represent, let alone govern, them.
The left's refusal to accept Trump is amusing since Trump himself fomented the birther movement against his predecessor in an attempt to garner attention for himself in preparation for his own presidential run. Trump's strategy to play upon the right's strings of distrust was effective at making him appear tough and persistent, with him constantly jibing at Obama to produce his birth certificate. Even when Obama did just that, Trump had the temerity to boast that he gets results, which was curiously true—though not relevant—as others had attempted ineffectually to goad the president into showing his birth certificate.
Of course others on the right never accepted Obama for other reasons, different but as absurd as questioning his citizenship. Some right-wingers really thought he was a Muslim, others delegitimized him because he was not white, others thought the 2008 election was stolen in ballot shenanigans. Some people just couldn't reconcile that someone with such a leftwing agenda could be president; he must be un-American. Some people simply didn't take him seriously on account of his youth and inexperience. Whatever the reason, Obama was illegitimate in the eyes of many right-wingers from the get-go, just like his predecessor, G. W. Bush.
The ballot shenanigans of the 2000 election certainly dwarfed anything that happened in 2008, with weeks of recounting and reexamining Florida's ballots until the issue of the recount was settled by the United States Supreme Court, who allowed an accounting of the ballots that resulted in a Bush victory. From the beginning, then, G.W. Bush was "selected not elected" in the eyes of many liberals.
(So illegitimate and hated was Bush that it became not uncommon to hear liberals wishing he would just die, and such was even publicly depicted, paving the way for Kathy Griffin's infamous cover of her holding Trump's severed head.)
In the 2000 election the U.S. Supreme Court was seen widely by the left to have acted in blatantly partisan, inherently anti-democratic bias, an outrage the left took badly after seeing their previous guy, Bill Clinton, was dogged for years by accusations of sexual harassment for years, humiliated in the Monica Lewinsky scandal, and then ultimately hauled into impeachment hearings. The left perceived that onslaught, which ended only in February of 1999 with Bill Clinton's acquittal, as instigated, fomented, and perpetuated by right wing partisans and a self-declared moral majority of self-righteous religious fundamentalist crusaders, all out to destroy their guy. This sentiment, infamously promoted by Hilary Clinton during the "Year of Monica" as a "vast right wing conspiracy," though not universally accepted even among the left the time, has become liberal dogma.
The scandal also set the left rather firmly opposed to the religious, and the left is not entirely wrong in feeling so opposed, I think, as some of the right-wing reaction against Bill Clinton was indeed driven in part by religious women's disgust at the sexual nature of the charges which they found impossible to reconcile with the dignity of the office. As such, the left remembers chiefly that disgust felt toward their guy, and many to this day will tell you with intense resentment that he was "impeached for a blow job," saying and thinking nothing of the charges of perjury, obstruction of justice, and abuse of power.
Fast forward and escalate that resentment for twenty years—through the indignity of enduring the Bush "I'm the decider" years, the seemingly final victory of the left under Obama vanishing in 2016 with the rise of Trump and the fall of the corporate press—and it's not hard to understand the animus driving their hostility toward Trump, whom many on the left, even moderates, want to see not only defeated, not only disgraced, but punished.
Trump's presidency is itself, and mostly I think, the right's vote of no confidence in the pre-2016 political status quo, in which they realized no principled republican could ever win: they brought Trump in precisely to give the left a bloody nose.
That blow having been dealt—socially if not in policy—it seems now that many on both sides are unable or unwilling to consider any representative of the other side as a legitimate chief executive and representative of popular will, despite the promises or processes that bring the candidate to the office. Whether this is peak POTUS legitimacy crisis and people will moderate, or it will continue to escalate, we will see.
