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Often he came on his way to or from the United States or to host a meeting with the American President. He saw Canada as a vital link - the 'linchpin' he called it - of the English-speaking peoples.
In Winnipeg in 1901 he heard of the death of Queen Victoria and headed home to begin his amazing political career.
In Toronto in 1929 the Imperial Statesman drew such large crowds that speakers had to be placed outside the Royal York Hotel.
In Calgary in 1929 he wrote to his Wife that he was thinking of retiring from politics and taking up a business career in the Canadian West.
Off the coast of Newfoundland in 1941 Churchill and Roosevelt formed the Atlantic Alliance and later that year in Ottawa he spoke in the House of Commons and sat for Karsh to take what has become one of the most famous photographs in history.
In Quebec City in 1943 a conference between Churchill and Roosevelt planned Operation Overlord, the invasion of Normandy which occurred the following year.