I think you are underestimating two very powerful cultural forces and not giving enough credit to the fact the Clintons made their own bed of awful baggage.
First, the sheer amount of irrational hate Hilary Clinton generates among moderate-centrists and conservatives has lasted 20+ years. I linked a survey earlier that showed 53% of Trump voters said they were specifically voting Against Hilary. That was the highest number ever recorded since they started recording that stat.
Even more people voted specifically against Hilary than against Trump. Anyone who conducted focus groups instead of polls like Michael Moore and Frank Luntz could see how much more powerful the dislike for Hilary was than just about any other Democrat in history including the first black President. Its certainly an interesting phenomenon because Hilary is more center-right than most Democrats yet in my experience she was vastly more hated than even Obama, Warren or anyone. I definitely heard more random moderates and conservatives at airports, truck stops etc, just chatting mad shite about Hilary from 2008-2016.
Second, the progressive wing of the Democrat party had long abandoned her and her husband and that is the very base the Democrats need to motivate to get out the vote to win. Its important to remember that Bill Clinton was out there campaigning for Hilary. That alone is enough to turn off a lot of progressives who lived through the Clinton years. Defense of marriage act, Three Strikes Laws, Hilary's corporate alliances with Wal Mart (where she was on the Board in the 1980s when Bill was Gov in Arkansas) and Wall Street, etc made Hilary the weakest candidate possible at turning out the Democrat voter base.
There simply isn't another living person that could simultaneously piss off progressives enough to not vote for her while at the same time energizing the conservatives into a mad frenzied voter turnout. Literally no one.
Trump had an easy time because Hilary had 3 decades of hatred built up on both the moderate-conservatives and progressives. Its truly remarkable how she could piss off such two ideologically diverse groups at the same time.
Here is a great article on Clinton baggage. The Clinton's baggage was not invented by Trump. He simply tapped into the Democrats making the worst strategic decision in a nomination in the history of American politics. And before the objection that this article is on Bill its important to remember they really come as a couple - Hilary used her experience as First Lady heavily involved in policy as an argument for why she was qualified for Senator in 2000 so she can't have it both ways:
"Now, the relevance of all of this to the present election can be debated. It is typical for Hillary Clinton’s supporters to point out that holding Hillary accountable for her husband’s actions is unfair at best and sexist at worst. Hillary Clinton was, of course, a major power in Bill’s administration and his equal partner in a joint political venture. But more importantly, Bill’s recent comments have been made as part of the campaign. Bill was defending this record on behalf of Hillary Clinton, to thousands of her supporters. If Hillary Clinton didn’t have Bill Clinton out front speaking about the Clinton Administration, it might be fair to ask people not to associate them. But since she has chosen him to be an ambassador for her message, we must at least assume that she does not think him as heinous as the record proves he is."
"A theme therefore runs through Clinton’s entire political career: black lives have never mattered to him, except to the extent that they conferred black political support. "
"But in order to understand Clinton, it is important to set aside the idea that his heart must necessarily have been in the right place. The evidence suggests something different, something far simpler and more logical: Clinton treated black interests with total mercenary cynicism. If cultivating their support helped him, Clinton would go to every length to connect with black voters. But the moment he faced a difficult choice between the politically expedient thing to do and the racially just thing to do, there was quite literally no harm he was unwilling to inflict upon black people in order to secure even minor political victories.
This was most starkly evident in criminal justice. From the very beginning, Clinton made a point of, as Alexander puts it, “signaling to poor and working-class whites that he was willing to be tougher on black communities than Republicans had been.” This is not just speculative interpretation on Alexander’s part; Clinton made it quite clear. During the 1992 election, just before Super Tuesday, Clinton traveled to Stone Mountain Correctional Institution in Stone Mountain, Georgia. There, he stood next to conservative Southern Democrats Sam Nunn and Zell Miller, as well as Dukes of Hazzard star Ben Jones (recently heard prominently defending the Confederate flag), posing for photographers in front of a group of black inmates. (See image above.) Clinton quite literally made a prop out of a group of convicts...
Another 1992 incident displayed that ruthlessness even more starkly: the execution of Ricky Ray Rector. It’s a chapter in Clinton political history that has become moderately infamous, but most accounts fail to convey the full calculating brutality of Clinton’s actions...
Ricky Ray Rector was a black prisoner in Arkansas who had been convicted of murder and was scheduled for execution. But Rector was severely brain damaged, having shot himself in the head after shooting the victim; he was missing one-third of his brain and had been effectively lobotomized. As a result, Ricky Ray Rector’s mental functioning was that of a very young child...
Clinton refused to grant clemency. Rector was executed on January 24, 1992. It is unlikely he had any idea what was about to happen. When he had his last meal, Rector set the dessert aside for later, even though there wouldn’t be a later. And in a pitiful and poignant detail, the night before his execution, watching Clinton on television, Rector said that he planned to vote for him in November.
There was no mystery as to why Clinton had refused to grant Rector clemency. Earlier in his political career, Clinton had lost a race against a “law and order” candidate, and those around him said he was determined not to make the same mistake twice. And it worked:
Intended or not, in the following months the political value of Rector’s execution became abundantly clear. It knocked the law-and-order issue out of the campaign. One commentator said it showed Clinton was “a different sort of Democrat.” As another put it, “he had someone put to death who only had half a brain. You don’t find them any tougher than that.”
Or, as former prosecutor and Arkansas ACLU director Jay Jacobson said, “You can’t law-and-order Clinton… If you can kill Rector, you can kill anybody.” In the general election, the National Association of Police Organizations endorsed Clinton over Bush, and so did a law enforcement group in Bush’s home state of Texas.
Clinton did not just simply allow Rector to die, however. In fact, he was active in using Rector’s death politically, flying back to Arkansas just so he could be there for the execution. As The Guardian reported:
The same week, Gennifer Flowers came forward with her story of a 12-year affair with the candidate. Beset by crisis, Governor Clinton broke off his campaign in New Hampshire to return to Little Rock for Rector’s execution. There was no legal obligation on him to do so; as the Houston Chronicle remarked, “never – or at least not in the recent history of presidential campaigns – has a contender for the nation’s highest elective office stepped off the campaign trail to ensure the killing of a prisoner.”
The Ricky Ray Rector case has been mentioned from time to time as a controversial Clinton act. But it’s important to be clear about just what Clinton did: he deliberately had a hallucinating disabled man killed, in an execution so callous it made even the warden queasy. He personally ensured the execution of a mental child so as not to appear weak...
But there are plenty of other, less viscerally appalling instances of the same phenomenon: Clinton shoring up political support by demonstrating that he was more willing than Republicans to inflict harm and suffering on black people, securing the black vote through words and the white vote through deeds.
This is precisely what happened in criminal justice policy. When the United States Sentencing Commission recommended that Clinton close the 100-to-1 disparity in sentencing for crack and powder cocaine, Clinton refused, in a decision Jesse Jackson called “a moral disgrace,” and observing accurately that Clinton was “willing to sacrifice young black youth for white fear.” In his own defense, Clinton said that “I am not going to let anyone who peddles drugs get the idea that the cost of doing business is going down. "
https://www.currentaffairs.org/2016/04/bill-clinton-has-always-been-this-person
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