Babe Ruth

Babe Ruth earned roughly $910,000 in total MLB salary across his entire 22-year career. Adjusted for inflation, that's about $17 million — less than the league minimum for a single modern season. His peak salary of $80,000 in 1930 was the highest in baseball and more than President Hoover's $75,000. His response when questioned about it became the most famous salary negotiation quote in sports history.

The Sultan of Swat spent money like he was allergic to it. He was legendary for picking up dinner tabs for entire restaurants, buying rounds for strangers, gambling heavily on horses, and maintaining a lifestyle that included custom suits, luxury cars, and an entourage of drinking buddies. His first wife Dorothy estimated he spent $1,000 a day during the off-season — in 1920s dollars, that's roughly $17,000/day today.

When Ruth died in 1948, his estate was valued at approximately $800,000 — impressive for the era but a fraction of what he earned. The tragedy isn't that he died poor (he didn't), it's the gap between what the greatest baseball player of all time earned and what even average modern players make. Mike Trout's single-year salary ($37M) is more than Ruth earned in his entire career, adjusted for inflation. Ruth built baseball into America's pastime and was compensated like a regional manager.