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Until the final months of his failed 2013 campaign for reelection as mayor of Rochester, N.Y., Thomas Richards enjoyed a charmed career. He repeatedly leveraged legal jobs into executive posts—from litigation partner to managing partner of what is now Nixon Peabody; from general counsel to CEO of the local energy utility, which cut him loose with a $10 million golden parachute after a merger; and from Rochester city corporation counsel to mayor, a position that he won in a special election when his predecessor became New York’s lieutenant governor.

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