8. Vince Taylor

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In what might be considered an epic tale of a two-time loser, Taylor was another one of the few who managed to win the lottery twice. His first win netted him £1.3 million which enabled him to move into a mansion with its own stables and swimming pool. The purchase of luxury automobiles further diminished his winnings and he was broke by 2001. In an amazing stroke of luck, Taylor won again, this time it was £120,000 – not as good at his first win but certainly a nice windfall for someone who was broke. Bad investments relieved Taylor of his last winnings and he ended up taking on a job as a bricklayer to make ends meet.