Steve & Elaine Wynn – $741 million
After meeting in college, Steve and Elaine Wynn married in 1963. 13 years later, the couple divorced; only to get married again five years later.
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Steve managed to strike out twice with the same woman because they divorced for the second time in 2010. The divorce cost the billionaire $741 million in Wynn stock at the time of the settlement. Both of them continued to work at the company.