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This could be either pre- or post-1900, but the possibilities I could think of are all post-1900:

(1) The American novelist and Progressive Republican politician Winston Churchill https://www.alternatehistory.com/forum/threads/the-other-winston-churchill.402219/ is more successful in politics--and ends up being POTUS at the same time Winston Churchill is Prime Minister of the UK.

(2) Congressman John Coffee https://en.wikipedia.org/wiki/John_M._Coffee becomes president of the United States at the same time João Café Filho (i.e., John Coffee, Jr.) is president of Brazil. https://en.wikipedia.org/wiki/Café_Filho

(3) Unfortunately, Governor Raul Castro of Arizona https://en.wikipedia.org/wiki/Raúl_Héctor_Castro was ineligible for POTUS, having been born in Mexico.

(4) Maybe John Smith https://en.wikipedia.org/wiki/John_Smith_(Labour_Party_leader) lives and leads Labour to victory in the UK--while Hans Schmidt https://en.wikipedia.org/wiki/Hans_Christian_Schmidt (who in OTL held a number of cabinet positions) becomes Prime Minister of Denmark.

(5) Senator Joseph Clark, Jr. of Pennsylvanis https://en.wikipedia.org/wiki/Joseph_S._Clark_Jr. becomes POTUS--maybe he is elected VP as Humphrey's running mate in 1968, Humphrey wins, Humphrey dies in office, and Clark is elected POTUS in his own right in 1976. He is still POTUS when Joe Clark become Prime Minister of Canada in 1979... https://en.wikipedia.org/wiki/Joe_Clark

(6) Gord Brown https://en.wikipedia.org/wiki/Gord_Brown becomes Conservative Prime Minister of Canada at the same time Gordon Brown https://en.wikipedia.org/wiki/Gordon_Brown is Prime Minister of the UK.
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