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10 biggest contracts handed out in the history of MLB free agency

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The amount of money in baseball continues to grow, and with it, the biggest MLB free agent contracts grow as well.

For fans who need MLB free agency explained, just assume that players will go to the highest bidder. That’s part of the reason why records for the largest contracts in MLB free agency seem to be rewritten with each offseason, and that doesn’t even include the extensions some players have received before reaching free agency.

10 biggest MLB free agent contracts

Not surprisingly, some of the biggest MLB free agent contracts ever signed end up also being among the worst contracts in MLB history.

Of course, since all of these deals are guaranteed, the players don’t mind that. It’s the teams that take on the most risk when signing a player to one of the biggest baseball contracts of all time. In any event, to showcase just how crazy MLB free agency has gotten, we decided to look at the 10 largest contracts in MLB free agency ever.

10. Anthony Rendon & Stephen Strasburg – 7 years, $245 million

The good news is that Rendon and Strasburg were both instrumental in the Nationals winning the 2019 World Series with Strasburg winning World Series MVP.


The two then signed identical seven-year, $245 million contracts the following offseason with Strasburg opting out of his deal but staying in Washington while Rendon signed with the Angels. The bad news is that both teams have gotten the short end of those deals, as both Rendon and Strasburg have been held back by injuries since signing their contracts.

9. Alex Rodriguez – 10 years, $252 million

When this contract was signed, it was the biggest ever. In fact, if it was signed today, that $252 million would be equal to about $400 million and it would still be the biggest contract ever. Nevertheless, the last-place Rangers were determined to do whatever it took to become a winning franchise.

The problem is that sinking over $25 million a year into one player isn’t always a wise choice. In three seasons with A-Rod in Texas, the Rangers failed to finish with a winning season. When Aaron Boone hurt himself in a pickup basketball game, Texas received a lifeline, as the Yankees showed interest in trading for A-Rod, taking him and most of his contract off their hands.

8. Alex Rodriguez, -10 years, $275 million

In a weird way, it’s fitting for A-Rod to be on this list twice. Seven years into the 10-year deal he signed with the Rangers in 2001, A-Rod opted out of that contract so he could sign an even bigger deal to stay with the Yankees.

Rodriguez would ride that contract to the end of his career, albeit with a one-year suspension for his connection to PEDs. He probably didn’t live up to the $275 million price tag, but he was there in 2009 when the Yankees won the World Series.


7. Xander Bogaerts – 11 years, $280 million

Imagine having one of the best young shortstops in baseball and giving him a four-year extension worth $340 million to keep him with your team for the long haul. The only natural thing to do is to spend $280 million on a free-agent shortstop two seasons later.

Somehow, that scenario made sense to the Padres when they signed Bogaerts ahead of the 2023 season. In fairness, Fernando Tatis Jr. missed all of the 2022 season with an injury and then a PED suspension. He’s also athletic enough to move to another position.

Nevertheless, the Padres continued their recent spending spree by giving the 30-year-old Bogaerts an 11-year contract that will make him and Tatis teammates for more than a decade.

6. Trea Turner – 11 years, $300 million

This isn’t the only contract on the top-10 list given out by the Phillies. When MLB teams went wild with spending before the 2023 season, Turner was one of the top benefactors, getting $300 million to play in Philadelphia.

For what it’s worth, the Phillies spent several years playing against Turner when he was with the Nationals, helping Washington to a title in 2019, so the Phils know what they’re getting with such a big investment.

5. Manny Machado – 10 years, $300 million

This is another contract that was once the record-holder for the richest contract in North American sports history. A few years earlier, nobody would have expected the Padres to pay this amount of money for a single player.

But San Diego has become one of MLB’s biggest spenders in recent years.

However, few would have foreseen them going so far as to promise Machado $300 million, even if he’s done a decent job of living up to it during the first few years of the deal.

4. Gerrit Cole – 9 years, $324 million

Among pitchers, Cole has the largest contract in MLB history. Not surprisingly, the Yankees were the team so inclined to set that record. To be fair, when Cole hit free agency after the 2019 season, he was arguably the best pitcher in baseball, leading the American League in both ERA and strikeouts that season.

He’s continued to pitch well in pinstripes, although he’s yet to match what he did in 2019. Plus, his salary comes out to more than $1 million per start, so it’s tough to argue that Cole is living up to that contract.

3. Corey Seager – 10 years, $325 million

At first glance, it’s surprising to see Seager this high up on the list. While he was an all-star in 2022 right after signing this deal with the Rangers, it was the first time he was an all-star since 2017.

Granted, he did win NLCS and World Series MVP in 2020 when the Dodgers won a championship. But it’s hard to argue that Seager is worth more than some of the other players below him on this list. However, Texas was desperate for some offensive firepower during the 2022 offseason, and they were willing to pay whatever it took to get Seager.

2. Bryce Harper – 13 years, $330 million

When Harper signed what at the time was the richest contract in the history of North American sports, it wasn’t just the total but the years the Phillies gave him.

To his credit, Harper got his GED at a young age and went to junior college when he was just 17 with the hopes of expediting his path to the big leagues and reaching free agency sooner. The plan worked because he was only 26 when the Phillies gave him that 13-year deal, much to the chagrin of the folks in Washington, where Harper spent the first seven years of his career.

After winning MVP in 2021 and helping the Phillies get to the World Series in 2022, the mega-contract seems to be working out for both Harper and the Phillies.

1. Aaron Judge – 9 years, $360 million

Heading into the 2023 offseason, the Yankees were already responsible for some of the biggest MLB free agent contracts ever signed, so why not recapture their record? Obviously, only time will tell if this ends up being a good deal or one of the biggest mistakes in MLB free agency ever made.

Judge was already 30 when he signed the deal, so it’s not like he’s a spring chicken. Of course, Judge couldn’t have picked a better time to hit the open market. He was coming off an amazing 2022 campaign in which he belted 62 homers and drove in 131 RBIs while hitting .311.

It was one of the best seasons a hitter put together in a long time. With the Yankees well over a decade removed from their last World Series win, they couldn’t afford to have their biggest star sign elsewhere, so they had to pay a record-setting amount of money to keep Judge.

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