Multiple realities
(covers information from several alternate timelines)

Sir Winston S. Churchill was a Human who served as Prime Minister of Old Britain during Earth's World War II.

In 2152, Malcolm Reed compared a speech of Chancellor Kultarey, a political leader of Gosis' species, to those of Churchill before World War II. (ENT: "The Communicator")

In an alternate timeline, Churchill made a wartime unity speech to improve Allied morale which was broadcast over radio in 1944. Aboard Enterprise, Hoshi Sato picked it up and replayed part of it for T'Pol, Tucker, Reed and Mayweather: "…as to the youth of all the Britons, I say, 'You cannot stop.' There is no halting-place at this point. We have now reached a stage in the journey where there can be no pause. We must go on. It must be world anarchy or world order." (ENT: "Storm Front")

The speech was an actual speech by Churchill, called "The Gift of a Common Tongue" (aka "The Price of Greatness") [1]. It was in reality delivered on September 6, 1943 at Harvard University in Cambridge, Massachusetts. (Star Trek Encyclopedia (4th ed., vol. 1, p. 143)) Presumably the alternate speech was delivered under different circumstances, since Massachusetts was under German control. In fact, Churchill's whereabouts or activities at this time are wholly unclear, as England too had fallen to Hitler early in the war.
In a developmental memo Gene Roddenberry wrote Robert Justman about TOS: "The Enemy Within" (dated 23 May 1966), Roddenberry postulated, "Churchill, without discipline, could have become the arch-criminal of the Twentieth Century." (In the memo's next sentence, Roddenberry made a similar observation about Harry S. Truman.)

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