Winston Churchill became prime minister of Britain the same day the Germans launched their attack against France and the Low Countries in May, 1940. The situation went from bad to appalling in very short order as the vaunted French army’s high command crumbled under the stress (even if the soldiers fought bravely in most cases). The British Expeditionary Force retreated with the French mobile forces toward the English Channel, eventually evacuating as many troops as they could from the port of Dunkirk. During this time, Churchill was appealing to the American President Franklin D. Roosevelt for whatever aid he could send.
Postwar histories tended to portray FDR as both benevolent and helpful toward Churchill in this stressful period, but behind closed doors FDR was far less a future ally, as Andreas Koureas explained on Twitter:

More than a year after FDR’s attempt to pry Canada and the Royal Navy away from a “dying” Britain, he and Churchill met onboard HMS Prince of Wales, in Placentia Bay, Newfoundland, during the Atlantic Charter Conference. President Franklin D. Roosevelt (left) and Prime Minister Winston Churchill are seated in the foreground. Standing directly behind them are Admiral Ernest J. King, USN; General George C. Marshall, U.S. Army; General Sir John Dill, British Army; Admiral Harold R. Stark, USN; and Admiral Sir Dudley Pound, RN. At far left is Harry Hopkins, talking with W. Averell Harriman.
US Naval Historical Center Photograph #: NH 67209 via Wikimedia Commons.
Ironically, the truth is that in 1940, Roosevelt — behind closed doors — behaved worse than Trump.
On the 20th May 1940, after multiple failed pleas for aid, Churchill wrote to Roosevelt that:
“If members of the present administration were finished and others came in to parley amid the ruins, you must not be blind to the fact that the sole remaining bargaining counter with Germany would be the fleet, and if this country was left by the United States to its fate no one would have the right to blame those then responsible if they made the best terms they could for the surviving inhabitants. Excuse me, Mr. President, putting this nightmare bluntly.”
Roosevelt’s refusal for aid was understandable given the political situation in America. As he told Churchill earlier that month, it wasn’t “wise for that suggestion to be made to the Congress at this moment”.
However, what he did after the 20th May telegram wasn’t.
Not bothering to even reply to Churchill’s warnings, Roosevelt instead sought to get Canada to give up on Britain.
As Roosevelt thought that Britain would likely collapse, and Churchill could not be trusted to maintain the struggle, he summoned a delegation for Canada.
The aim was to get Canada to pester Britain to have the Royal Navy sent across the Atlantic, before Britain’s seemingly-inevitable collapse.
Furthermore, to ensure this, the Americans wanted Canada to encourage the other British Dominions to get on board such a plan, and likewise gang up against Britain.
You can see Mackenzie King’s (PM of Canada) disbelief and horror in his diary,
“The United States was seeking to save itself at the expense of Britain. That it was an appeal to the selfishness of the Dominions at the expense of the British Isles. […] I instinctively revolted against such a thought. My reaction was that I would rather die than do aught to save ourselves or any part of this continent at the expense of Britain.”
King telegrammed Churchill on the 30th May that this was the closed-door political situation across the Atlantic.
Bear in mind, Roosevelt was trying to instigate this during the Dunkirk evacuations.
How Churchill didn’t break knowing the one ally he needed in his darkest hour thought he’d fail, I have no idea.
On the 5th June 1940, Churchill wrote back to Mackenzie King,
“We must be careful not to let the Americans view too complacently prospect of a British collapse, out of which they would get the British Fleet and the guardianship of the British Empire, minus Great Britain. […] Although President [Roosevelt] is our best friend, no practical help has been forthcoming from the United States as yet.”
(The first key mover that swung Roosevelt into entrusting Churchill to continue the struggle — and as such aid would not be wasted on Britain — was when Churchill ordered the Royal Navy’s Force H to open fire and destroy the French Fleet at Mers-el-Kébir — after Admiral Gensoul had refused the very reasonable offers from Britain, despite Germany and Italy demanding the transference of the French Fleet as part of the armistices.)