At what point did you realize Trump was going to lose?

[EJ24]

?

[ProgressiveModerate]

Wasn't till COVID started that I though Democrats were notable favorites, but I think that week that he got COVID and had a terrible debate was the nail in the coffin.

[brucejoel99]

I thought he'd lose since the day he was elected. The only time during his presidency that I ever seriously feared a win being possible was when his approval rating started approaching ~50% at the beginning of COVID, but then he immediately started f**king things up & failed to garner any more of a rally 'round the flag effect, unlike basically every other world leader, so my fear soon subsided.

[It's Time.]

A few days after George Floyd died.

[Gracile]

There were a number of things in hindsight, but giving up on passing a COVID relief deal before the election was probably the biggest indicator.

[Roll Roons]

When he made the bleach comment.

[Trump Is A Maoist]

When Michigan and Wisconsin mail-in ballot results started coming in around 3:30am.

[Da2017]

When he bungled the covid response back in March.

[cp]

When Michigan and Wisconsin mail-in ballot results started coming in around 3:30am.

This, but a little later. Maybe when Wisconsin was called a bit later that day.

All the options in the poll felt like they ought to have been the final die being cast, but after the past 4-5 years I've stopped believing anything is truly disqualifying, no matter how heinous it is (this applies to the UK too).

[Nightcore Nationalist]

When Saint Bernard got crushed on super tuesday.

[25 Abril/Aprile Sempre!]

I was always confident that Trump would lose, certainly since I started following closely American politics around summer 2019, but I wouldn't say it was a confidence based in rationality necessarily.

[Sumner 1868]

When his campaign became framed around Fox News rants about "socialism" sometime in late 2019 instead of combining a certain amount economic populism with culture war rhetoric like in 2016.

[Motorcity]

Around 12-3am on election when Biden spoke and was super confident and he took the lead in WI and MI

Before that I thought Trump was going to win. That was a rough night. I was sweating and my anxiety was up. It was horrible

[Hammy]

Trump getting COVID erased most of my doubts pre-election. Post-election was when Trump's lead in PA shrank enough that it became impossible to make it up.

[BoJack Horseman]

I was pretty sure Biden would sail through the rest of the primary and win in November after Mike Bloomberg’s campaign died a nationally televised death in the debate on February 19. By Wednesday afternoon it was obvious to any rational observer that Trump’s lead wasn’t big enough to withstand the mail-in ballots and it was only a matter of time before Biden took the lead in the Midwest.

Trump getting Covid and then spending three days rage-tweeting while in the hospital was when I knew for sure that the election was over.

[Red Wall]

When the fox decision desk called Arizona for Biden.

[Morgan Kingsley]

Around may or june I started to suspect, with full expectation and acceptance by September

But the election was so close that I then believed he would win against and did so far nearly 2 days

[JGibson]

When he bungled the COVID-19 pandemic response.

[here2view]

I felt pretty confident throughout the spring and summer that Trump would lose, but I knew that he was d-o-n-e, done after the double whammy of the first debate on September 29th and then him testing positive for COVID-19 on October 2nd.

[Crumpets]

I started to think Biden was favored to win about a week into the summer protests when it was clear they were taking a heavy hit on Trump's numbers and COVID and the economy weren't going any direction that would help him. I started thinking Biden was heavily favored and started to get smug about it around the time the Hunter Biden debacle went absolutely nowhere and Biden was still getting double digit leads in national polls. I was pretty sure Team Trump had planned on that being their big closing argument for re-election.

On election night, there were definitely a couple hours when I went back to thinking Trump was favored, but after going to sleep and reading through where things stood the next morning, I went back to thinking Biden was favored. Once Wisconsin was called, it really felt like it was just a matter of time before Biden was declared the winner and there was no feasible path for Trump.

[Skill and Chance]

The anti-mask stuff in the late spring/summer made him an underdog for the first time.  The first debate made it look like he was certain to lose but then he made up a lot of ground in the second debate, so I would say the debates cancelled out. 

[dw93]

I'll answer by saying how I felt about this at many points during his Presidency:

Nov. 2016 - Dec. 2017: I thought he was gonna lose and lose bad.The GOP hadn't fully rallied behind him yet, the Russia investigation was starting, Charlottesville happened and he responded by calling white supremacists "good people," he was trying to stumble into a war with North Korea, and his Tax Cut looked dead on arrival. There was also my belief that he'd preside over a recession at some point in his term. It wasn't until the Tax Cut passed that things changed.

Jan 2018 - Dec. 2019: I still though the odds were against Trump, but any loss would be closer than many were expecting. While the GOP did rally behind him, the Mueller report didn't amount to anything damning for Trump, and the economy was still humming along nicely, his meeting with Kim Jung UN amounted to nothing, the Government was shut down for over a month in late '18 and early '19, plus there was the Ukraine Scandal.

Dec. 2019 - April 2020: It was in this time frame that the odds were in Trump's favor. While the markets were starting to get shaky, the economy really didn't noticeably dip until March, Impeachment backfired on the Democrats (for reasons both within and beyond their control), and even a near war with Iran really didn't phase anyone. There was also the fact that the Democrats really didn't get their sh**t together until late April. Plus, Trump's approval ratings neared 50% due to the early rally around the flag effect in the early days of COVID, and his mishandling wasn't evident at that time.

May 2020 - Nov. 2nd 2020: He was back on the losing side of things. Outside of a brief period in early June where I thought he'd pull a Nixon and win on a law and order campaign due to the Democrats soft response to the looting and rioting, Trump did himself no favors and even the "law and order " stuff didn't get much traction in the end due to Trump mostly fanning the flames. The god awful first Debate and the COVID diagnosis were IMHO the cherry on top of a loss.

Nov. 3rd - Dec. 2020: I took the entire election week off work and I'm glad I did. Late on election night, I though Trump just might pull it off. Then the next morning, Biden took the lead in WI and MI with the mail in ballots coming in and FOX's declaration of AZ for Biden hadn't changed. Once Biden was declared the winner in WI, I knew Biden was gonna win, the question is to what length would Trump and the GOP go to steal it and would they succeed? Barr launching an Investigation from the Justice Department scared the hell out of me as I saw it as a huge overreach and abuse of power. After this, and after the Legislatures in MI, PA, and WI said they would respect the result and certify Biden, I knew it was over, and that any of Trump's attempts to overturn the election, as damaging as they would be to the institutions and to democracy itself, would fail and Biden would be President.

[Chips]

I had him losing throughout August, September and October.

My final prediction had the 2016 map-WI and MI so I was never confident Trump would lose before the election.

I realized he would've lost once AZ was called.

[Chips]

When Michigan and Wisconsin mail-in ballot results started coming in around 3:30am.

Also this.

[Mr. Smith]

Overall: When he got COVID himself.

Election Night: I compiled my 10 PM Map and Biden was ahead...who leads at thatfixed point in time simply doesn't lose...botched Florida calls aside.