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In the late 1950s, New York Yankees catcher Yogi Berra paid the bills by working in the offseason as a waiter. This was not uncommon. Shortly after shutting out the Los Angeles Dodgers in Game 2 of the 1966 World Series, Baltimore Orioles pitcher Jim Palmer supplemented his income to the tune of $150 a week selling suits at a men’s clothing store. NFL legend Jim Brown held a side gig as a sales rep with Pepsi, Hall of Fame quarterback Y.A. Tittle sold insurance and Dodgers outfielder Carl Furillo ran a deli.

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Today’s top players don’t have to worry about working a side gig in the offseason. Nine-figure contracts, once unheard of, are now the norm for the biggest sports stars. Some of the largest contracts are spread out over a dozen years or more. Other athletes collect much more quickly, raking in untold riches in a little more than two years.

In this study, GOBankingRates aggregated noteworthy contracts across multiple sports and ranked the most lucrative ones in descending order, from lowest to highest. The study used data from Spotrac, MLB and ESPN to dig into the contracts further. Boxing, baseball and basketball contracts came out on top. In some cases, more than one player tied with the same contract value, so readers should expect to see some values repeated.

Keep reading to find out which players inked the deals that made them the highest-paid athletes in history.

Last updated: July 12, 2021