Teddy Roosevelt had Theobald Chartran do his first portrait in 1902. After the portrait was finished, teddy hated it. He hired John Singer Sargent to do his portrait. That was Teddy's portraitist.
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That's pretty open ended. There could be a healthy debate among the many worthy candidates: Churchill, Ghandi, Mandela, Reagan, the Roosevelts (Teddy, FDR and Eleanor) ...
He expected victory.
he understood the varius needs of his audience
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Middle America: Panama, Cuba and Venezuela.