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.

Then, in his bid last fall for a full term as mayor, the 70-year-old Richards stumbled. After a half-hearted campaign, he lost the Democratic primary; days later, his 37-year-old son Matthew, a father of two, succumbed to cancer. When supporters mounted a third-party campaign to retain him, Richards seemed ambivalent, producing political chaos that cut against his reputation for steady, businesslike leadership. His real struggle broke into view at one contentious press conference, where he snapped, “Do I want to be mayor? I want to be a grandfather more.”