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What would have happened if Franklin Roosevelt had followed his uncle's footsteps and joined the Republicans when staring out as a politician? In many ways it was his natural political home.
There are parallels with Tony Blair joining Labour instead of the Tories, but I think the FDR case is both more significant and less explicable. Blair joining the Labour Party is at least partly explained by his wife and his mentor. And we won't know the full story with Blair until a definitive biography appears.