"With Universal Mail-In Voting (not Absentee Voting, which is good), 2020 will be the most INACCURATE & FRAUDULENT Election in history. It will be a great embarrassment to the USA. Delay the Election until people can properly, securely and safely vote???" Mr Trump tweeted.
The president's concerns with mail in voting have been debunked by elections experts. But could he actually move the election?
Joe Biden, the presumptive Democratic challenger to Mr Trump, issued an unsettling warning to his supporters in April about the subject.
"Mark my words, I think [Trump] is gonna try to kick back the election somehow, come up with some rationale why it can't be held," he said during the event. "That's the only way he thinks he can possibly win."
The charge would raise sceptical eyebrows under normal conditions. But in the coronavirus-embattled world we now inhabit, in which billion dollar sports leagues cancel seasons and states postpone - or even cancel - their primaries, is it really that absurd to think Mr Trump could delay the 2020 election?
Mr Trump doesn't have the power to move or otherwise postpone the election. That power - to determine the "Times, Places and Manner of holding Elections" - is granted to the Congress by way of the US Constitution.
The US Constitution mandates that every state votes on the same day and that the states determine a number of electors who ultimately elect the president. US Code builds on that, establishing that those electors "shall be appointed, in each State, on the Tuesday next after the first Monday in November, in every fourth year succeeding every election of a President and Vice President."
With Universal Mail-In Voting (not Absentee Voting, which is good), 2020 will be the most INACCURATE & FRAUDULENT Election in history. It will be a great embarrassment to the USA. Delay the Election until people can properly, securely and safely vote???— Donald J. Trump (@realDonaldTrump)July 30, 2020
In fact, as noted by Dr Erwin Chemerinksy, Dean of Berkeley Law, even if Congress chose to postpone the election, it wouldn't mean Mr Trump would remain in office beyond his term.
"President Trump has no authority to postpone the November election. Period," Mr Chemerinsky said. "In fact, if the election were postponed, Trump's term ends on January 20, 2021. If no one were elected president or vice president, the Speaker of the House would become president."
Responding to Mr Biden's allegations in April, Mr Trump previously said he looked forward to the election and that he wouldn't change the date.
"I never even thought of changing the date of the election. Why would I do that? November 3rd, it's a good number. No, I look forward to that election and that was just made up propaganda," Mr Trump said.
It appears 3 November, formerly a "good number," may have lost Mr Trump's favour.
Why did Mr Trump change his mind?
The president's query on the election date was probably triggered by a confluence of issues.
First, Mr Trump has been taking a beating at the polls in recent weeks, even in states that should be easy victories for the incumbent.
In Florida, polls show Mr Biden leading Mr Trump by 9 points. A Quinnipiac University survey suggested Mr Biden lead the president by 13 points in the Sunshine State.
Mr Biden also leads Mr Trump by 9 points in Pennsylvania, another state the incumbent won in 2016. A poll from Franklin & Marshall College's Center for Opinion Research reported the data earlier this week.
In Georgia, Mr Biden and Mr Trump are in a dead heat, despite the fact that Republicans have carried Georgia for nearly 30 years.
In addition to his poor polling, the coronavirus has only got worse in the US, as states rushed to reopen after a short lockdown, which - paired with a lack of testing and tracing efforts - thwarted the chances for isolating the virus.
Since then, spikes in coronavirus cases in several US states have all but extinguished any hope for normality come November.
As a result, the pressure to move to a mail-in voting system to prevent further outbreaks is likely. Mr Trump, as he revealed in his tweet on Thursday, would rather see the election moved than run in a race that allowed mail-in voting.
It's worth noting that Mr Trump himself has voted by mail - hence the caveat in his tweet about absentee voting being good - as has Vice President Mike Pence, the president's daughter Ivanka, her husband Jared Kushner, his press secretary Kayleigh McEnany, his cabinet members Attorney General William Barr, Secretary of Education Betsy DeVos, his trade adviser Larry Kudlow and the Secretary of Commerce Wilbur Ross. Even his previous campaign manager, Brad Parscale, has voted by mail.
Though Mr Trump's talking points on mail-in voting are always tied to voter fraud, the broader concern that he and his White House cohorts have is that it would make voting easier, which would undermine years of alleged Republican efforts to do the exact opposite through voter ID laws and voter-roll purges.
During an appearance on Fox and Friends earlier this year, the president discussed the "crazy" mail-in voting measures Democrats attempted to include in the CARES Act coronavirus relief package.
"The things they had in there were crazy. They had things, levels of voting that if you'd ever agreed to it, you'd never have a Republican elected in this country again," Mr Trump said. "They had things in there about election days and what you do and all sorts of clawbacks. They had things that were just totally crazy and had nothing to do with workers that lost their jobs and companies that we have to save."
Mr Trump's suggestion was that the higher the voter turnout, the worse Republicans would fare in the election.
That sentiment was echoed in 1980 by Paul Weyrich, an influential conservative activist who all but admitted that voter suppression was good for the GOP.
"I don't want everybody to vote," Mr Weyrich said. "As a matter of fact, our leverage in the elections quite candidly goes up as the voting populace goes down."
Between his lacklustre polling and the likely need for mail-in voting, Mr Trump may think that moving the election as his next best option.
Could he actually do it?
Dr Camila Vergara, a Postdoctoral Research Scholar at Columbia Law School's Eric H Holder Jr initiative for Civil and Political Rights, said even if Mr Trump attempted to use emergency powers, he couldn't - legally - remain in office.
"Some may argue the President could suspend elections using emergency powers, however, in the 136 of the statutory emergency provisions that he could use, there is no explicit power granting the President the prerogative to suspend or reschedule elections," Ms Vergara said. "Any use of such a power would be unprecedented and not grounded on existing legality."
Ms Vergara notes, however, that just because there is no legal way for the president to suspend the election and stay in office, doesn't mean it can't be done.
"However, the President, as the Commander in Chief, can always de facto suspend or reschedule elections, and even stay beyond 20 Jan; who would forcibly remove him from office if the military responds to him and the pandemic is still ongoing?" she said. "Challenges against these actions could only be launched ex post facto, through the courts or Congress through impeachment, and we all know how that went already."
Even if the president did overstay his term in office and even if the Supreme Court held that it was unconstitutional, Ms Vergara notes that months would pass before such a decision was made, and by that point the election would have already been suspended.
Since he's stepped into the Oval Office, Mr Trump has made a few questionable comments about his willingness to leave following a defeat.
In a tweet he made last June while complaining about The New York Times and The Washington Post, Mr Trump openly asked if people would demand that he stay and serve as president beyond his term limit.
.....news is that at the end of 6 years, after America has been made GREAT again and I leave the beautiful White House (do you think the people would demand that I stay longer? KEEP AMERICA GREAT), both of these horrible papers will quickly go out of business & be forever gone!— Donald J. Trump (@realDonaldTrump)June 16, 2019
A few months before that, Mr Trump echoed the call of Liberty University President Jerry Falwell, Jr, who suggested the president should get an extra two years because his first two were "stolen" by a "corrupt failed coup".
After the best week ever for @realDonaldTrump - no obstruction, no collusion, NYT admits @BarackObama did spy on his campaign, & the economy is soaring. I now support reparations-Trump should have 2 yrs added to his 1st term as pay back for time stolen by this corrupt failed coup— Jerry Falwell (@JerryFalwellJr)May 5, 2019
And on more than one occasion he's casually floated the idea of staying in the White House for "10 or 14 years" and suggested he deserves to get his "stolen time back".
Most recently, Mr Trump was unwilling to say he'd accept the results of the election during an interview on Fox News with Chris Wallace.
"I have to see. Look ... I have to see," Mr Trump said. "No, I'm not going to just say yes. I'm not going to say no, and I didn't last time either."
When asked how he would handle such a situation, Mr Biden said that he was confident the military would not allow Mr Trump to remain in office.
"I promise you, I'm absolutely convinced, they will escort him from the White House in a dispatch," Mr Biden said.
None of Mr Trump's comments are overt threats that the he intends to ignore the election results or will try to move its date, and he would likely brush the comments aside as jokes or sarcasm - a defence he and his supporters often use to downplay his comments.
The electoral battle that will likely be fought between the President and Congressional Democrats won't be over the date of the election, but more likely the method.
"In this next bill, we will be supporting vote by mail in a very important way - we think it's a health issue at this point," Ms Pelosi said.
Though recent polls suggest 58 per cent of voters are in favour of nationwide mail-in voting, Mr Trump is opposed to the idea and has called on Republicans to oppose the bill.
"Republicans should fight very hard when it comes to statewide mail-in voting. Democrats are clamouring for it. Tremendous potential for voter fraud, and for whatever reason, doesn't work out well for Republicans," Mr Trump tweeted.
Mr Trump's disdain for mail-in voting may also play into his administrations attempts to undermine the US Postal Service.
Speaking to The Washington Post, a White House official said the president wouldn't sign anything that included funding for the Post Office.
"We told [Democrats] very clearly that the president was not going to sign the bill if [money for the Postal Service] was in it," they said. "I don't know if we used the v-bomb, but the president was not going to sign it, and we told them that."
So, the question going into November is not likely going to be when we vote, but rather how we vote.