One of the biggest what-ifs of the 20th century, if not the entirety of world history, is "What if Hitler doesn't attack the Soviet Union"? Because Hitler wasn't supposed to attack the Soviet Union...
On August 23, 1939, Nazi Germany and the USSR signed a non-aggression treaty known as the Molotov-Ribbentrop Pact. A week later, Germany invaded Poland. Stalin was happy to see it burn, waiting for Eurasia to be divided between the two powers.
But the pact! Negotiations started earlier that year, but stalled. You see, in charge of the Soviet side was Maxim Litvinov, who came with some baggage. Litvinov was born with the much less Russian name of Meir Henoch Wallach, and wanted no part of making nice with Hitler. Hitler wanted no part of Litvinov as well, so Stalin fired him. "The Soviet Government intended to improve its relations with Hitler and, if possible, sign a pact with Nazi Germany. As a Jew and an avowed opponent of such a policy, Litvinov stood in the way." It's not often we quote Stalin at JONJ, but this one is rather significant.
Litvinov was replaced by Vyacheslav Molotov, a Stalin lackey, and soon, peace was made. Obviously, in June of 1941, Hitler broke the pact, which led to his eventual downfall.
Of course, if Litvinov was kept in charge of negotiations, there might have not been a pact, and whole modern history might have gone in an entirely different direction...
Another fascinating what-if.