I don’t know what Churchill thought of Monty as a person. Winnie was too astute a politician to leave anything for posterity that could be constured as derogatory to Britain’s one popular military hero of the war, even if Churchill knew he had some glaring personality flaws.
For which I will adapt one of my favorite lawyer jokes to Monty, who although married wasn’t considered much of a ladies’ man:
Q: What did Field Marshal Montgomery use for contraceptives?
A: His personality.
That’s funny. I don’t know if anyone liked Monty.
That’s hilarious. Besides which, if it ever actually came down to it, by the time Monty finally got “ready,” she’d have long ago lost interest.
In those days Monty would have been labeled “A confirmed bachelor”.