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0 of 8 Mark Lennihan/Associated Press Starting pitcher Kevin Brown made history at the 1998 winter meetings, becoming the first player in MLB to sign a $100 million contract when he inked a seven-year, $105 million deal with the Los Angeles Dodgers. In the years since, players salaries have exploded, and there have been 90 more contracts of $100 million or more, according to Baseball Prospectus. That number will continue to grow this offseason, with Trevor Bauer, George Springer and J.T. Realmuto potential candidates for nine-figure paydays. Will that be money well spent? We crunched the numbers to figure out how may $100 million free-agency deals have actually been worth it, based on production, health and postseason success.

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