Alex Rodriguez

Alex Rodriguez earned $441 million in MLB salary over his career -- the most in baseball history -- including a 10-year, $275 million contract with the Texas Rangers in 2000 that was the largest in professional sports at the time. His second mega-contract, a 10-year, $275 million extension with the Yankees in 2007, pushed his career playing earnings past $400 million. No baseball player has ever been paid more to play the game.

Rodriguez has been equally aggressive in business. A-Rod Corp, his investment and real estate firm, owns over 15,000 multifamily apartment units across the southern United States. He has invested in TruFusion (fitness), NRG esports, Hims (men's health), and multiple tech startups through his venture arm. He was part of the ownership group that attempted to purchase the New York Mets (losing to Steve Cohen) and has been involved in several sports-adjacent investment deals.

His media career includes a stint as an ESPN analyst, a Fox Sports broadcasting role, and multiple business reality shows. Rodriguez is among the most financially active former athletes in the world, treating his post-career with the same intensity he brought to the batter's box. His net worth of $350 million reflects both his massive playing contracts and his growing real estate and investment portfolio. The PED suspension that tarnished his legacy on the field has not slowed his deal flow off it.