Someone has to pay him. Following a 62-home run MVP season as a member of the Yankees, star outfielder and free agent Aaron Judge deserves one of the largest contracts in the history of baseball. Anything less than the eight-year, $300 million offer recently extended by New York would be an unprecedented betrayal of MLB’s ever-ballooning free agent market. But there’s a problem.

Every few years, a player improves to a point where his market price grows beyond what any team should feasibly spend on a single player. In a sense, he’s too good to be signed, and yet, it’s necessary that multiple teams vie for his talents. History tells us that the winner has a long road ahead.

Though Judge may demand one of the largest contracts in the history of the sport, he’s certainly not the first highly touted free agent. The fervent pursuits of players like Mike Trout, Mookie Betts and Bryce Harper should all be fresh in fans’ minds, as they all demanded high prices in recent years. But the intense efforts of the Angels, Dodgers and Phillies, respectively, to sign those players have not yet resulted in a championship victory for any of them. Many other teams have made similar blockbuster deals without championship success.

In fact, of the 20 highest MLB contracts of all time, only one has contributed to a team’s World Series victory. In 2008, the Yankees signed Alex Rodriguez to a nine-year, $231 million deal and they won the World Series the following season. They also spent $50 million more than any other team in the league in 2009 and extracted immense value from other highly-paid players like Derek Jeter, Mark Texeira and CC Sabathia.


A week of sports news in your in-box.
We find the sports news you need to know, so you don't have to.

Besides the Yankees, the 2012 Tigers and 2022 Phillies are the only other teams to reach the World Series carrying a top-20 contract.

The Tigers did everything they could to lock down Justin Verlander while also paying Miguel Cabrera and Prince Fielder more than $20 million each. But without extraordinary production from outfielder Austin Jackson and upstart pitcher Max Scherzer, it’s doubtful the team could have contended for a championship. The Tigers only had to pay Scherzer $3.7 million and Jackson $500,000.

Meanwhile, this year’s Phillies team was undoubtedly propelled by Harper’s resurgent playoff performance, one they had been waiting for since he signed his 13-year deal with the team in 2019. But paying comparable sums to pitchers Aaron Nola and Zack Wheeler in shorter deals proved even more valuable over the course of the 2022 season.

Even in success stories, it becomes clear that there is absolutely no correlation in baseball between signing players to massive contracts and winning championships. It takes a lot more than one player to win a World Series, and though payrolls are growing every year, these contracts still prevent many teams from spending more in other areas.

In 2030, Trout will be 39 years old. Betts and Harper will be 38. All of them will be on the same contracts they’re on now, and if none of them have won a championship by then, their contracts will have been massive failures for their respective franchises. Judge, already an injury-prone player at 30, will also be 38 by then, and the team that signs him now will still be paying him for his 2022 value. The clock will begin to tick as soon as he signs the dotted line.

Read more about:

Leave a comment

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

The reCAPTCHA verification period has expired. Please reload the page.

Listen to the uInterview Podcast!
Get the most-revealing celebrity conversations with the uInterview podcast!