Alex Rodriguez & Cynthia Scurtis: Madonna, Prenup Escalators, and $27 Million

What Happened

Alex Rodriguez, one of baseball's highest-paid players with a $275 million contract from the New York Yankees, married his high school sweetheart Cynthia Scurtis in 2002. When Cynthia filed for divorce in July 2008, she cited 'emotional abandonment' and named pop superstar Madonna as 'the other woman' in her court filing -- a bombshell that dominated New York tabloids for months.

The case was notable for its sophisticated prenuptial agreement, which included escalation clauses -- provisions that increased Cynthia's payout based on the length of the marriage. For each additional year they were married, the settlement amount grew. At six years of marriage, the prenup entitled her to approximately $12 million. Various infidelity and misconduct provisions reportedly triggered additional payouts.

The final settlement was reported at approximately $27 million, significantly more than the base prenup amount. Florida law, where the couple resided, generally enforces prenups strictly, but the escalation clauses and potential infidelity triggers pushed the number higher. Cynthia also received their Coral Gables mansion and primary custody of their two daughters.

The Rodriguez divorce highlighted two important innovations in prenuptial drafting: escalation clauses that reward longer marriages, and infidelity triggers that penalize cheating. These provisions made the prenup feel less like a 'divorce planning document' and more like a marriage incentive structure. Despite the drama with Madonna, the prenup worked as designed -- protecting both parties while providing fair compensation based on the marriage's duration and circumstances.

Legal Breakdown: Prenup Escalation Clauses

What This Means for Your Divorce