50. Curtis Schilling
Curtis Montague Schilling, celebrated as a Major League Baseball pitcher and later a BlazeTV commentator, experienced significant highs and lows throughout his career. On the field, Schilling achieved championship glory with the Arizona Diamondbacks and Boston Red Sox.
Off the field, he launched 38 Studios, aspiring to rival World of Warcraft with his own gaming creation. Despite initial optimism, the company quickly unraveled, declaring bankruptcy and violating the terms of a government loan, leading Schilling to lose millions and part with valuable memorabilia. Schilling then transitioned to ESPN as an analyst, a role he lost due to controversial social media activity, marking another tumultuous chapter in his post-baseball life.