In the dying weeks of the campaign, Trump appeared to reflect on the possibility of losing and didn't like the idea at all.
"Running against the worst candidate in the history of presidential politics puts pressure on me," Trump said during rally on October 16 in Georgia.
"Could you imagine if I lose? My whole life, what am I going to do? I'm going to say, 'I lost to the worst candidate in the history of politics.' I'm not going to feel so good. Maybe I'll have to leave the country?"
At a later rally he said: "If I lose, I will have lost to the worst candidate, the worst candidate in the history of presidential politics. If I lose, what do I do? I'd rather run against somebody who's extraordinarily talented, at least, this way I can go and lead my life."
Now that the worst appears to be happening The Washington Post has provided an insight into what went wrong with Trump's campaign.
Many are blaming Jared Kushner, Trump's son-in-law and senior adviser, who pulled together his own virus response team that undermined the official coronavirus task force, overseen by Vice President Mike Pence.
"The only constant in this campaign, from Day One, to the very last day, was Kushner," a Trump ally close with the campaign told the Post. "So if the president wins, Kushner deserves credit, but if he loses, Kushner deserves the blame."
Kushner, who is married to Trump's daughter Ivanka, reportedly made it clear that he and the President had final sign-off on all major campaign decisions but was often distracted by his White House duties including trying to secure a peace deal in the Middle East.
But the coronavirus pandemic seems to have been the issue that derailed the President's run.
Earlier this year many expected Trump to win a second term and internal polling reportedly showed he was ahead of Biden in Florida, Pennsylvania, North Carolina and Arizona in February.
Eight months later and Biden looks to have claimed both Pennsylvania and has taken the lead in solid Republican states Arizona and Georgia.
"Back in February, he had this re-election in his pocket. If it wasn't for Covid, he could have sat back on his laurels and won," Tom Bossert, the president's former homeland security adviser, told the Post. "He's always been better at controlling the narrative than the levers of government."
Trump's polling numbers tanked as the coronavirus pandemic continued.
Infectious diseases expert Anthony Fauci reportedly urged Trump and Pence to own the coronavirus problem rather than blaming others, because it was the only way to fix it.
But Trump continued to play down the threat and ignored warnings from Fauci, choosing to hold large events around the country.
He continued his attack strategy on Joe Biden, echoing his "Crooked Hillary" approach, by targeting Biden's son Hunter, as well as the divisive, racist and misogynistic comments he had become known for.
He even revealed to a crowd in Tampa that others were urging him to stop his attack on Hunter Biden because nobody cared, and instead focus on his success on the economy.
"I disagree," he said, as the crowd cheered. "You know, maybe that's why I'm here and they're not."
Trump also appears to have ignored his advisers' debate preparation, interrupting Biden and the moderator constantly during a combative first debate, during which he also failed to denounce white supremacy.
"The average American will choose a doddering old fool who is past his prime over a jerky bully every day of the week and twice on Sunday," a Trump ally close to the campaign told the Post.
While his final debate appearance was better, nearly 50 million Americans had already voted by that time.
Some believe Trump suffered from keeping the focus on himself and that few top staffers were willing to give the US President advice that he didn't want to hear.
"A successful re-election campaign really needs to be focused on disqualifying your opponent, but the president spent most of this year keeping the spotlight focused on himself, which is antithetical to a winning strategy," Senate Leadership Fund president Steven Law said.