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18. Frank and Jamie McCourt

Settlement Amount: $131 Million

The former owner and chairman of the Los Angeles Dodgers, Frank McCourt, made most of his money in the real estate development business, but was set to lose a healthy portion of it when it was announced that the couple was splitting after 30 years of marriage in 2009. In a messy divorce, McCourt fired wife Jamie as CEO of the Dodgers and as part of the divorce settlement, she relinquished her ownership stake in the team after receiving a $131 million settlement.

The settlement was reached in October 2011, several months after the Dodgers filed for Chapter 11 bankruptcy protection, which eventually required the team to be put up for sale. In March 2012, the Dodgers and the land surrounding the stadium sold to a group of investors for a record price of $2.15 billion. It was a surprise to most everyone in sports that the team would have such a high valuation, but since Jamie McCourt had relinquished her ownership stake, she was not eligible to benefit from the proceeds, leading The Wall Street Journal to pose the question: Jamie McCourt’s Share: Baseball’s Worst Deal?

Photo: Kirby Lee | WireImage | Getty Images