For all the angst about large, nine-figure MLB contracts when they’re first signed (welcome to the club, Dylan Cease, Kyle Schwarber and Pete Alonso), they actually tend to be decent investments.
Sometimes, you get a paradigm-changing superstar who uplifts your franchise to the promised land (e.g. Shohei Ohtani, Corey Seager, Max Scherzer). Other times, you get a guy who never quite reaches the highs of his previous years but manages to be a legitimate MLB player for at least a few years (e.g. Xander Bogaerts, Albert Pujols).
But rare is the contract in which, almost from the get-go, the player ceases to be a starter-quality MLB player, if he’s playing at all. At the very least, you should be getting a guy who can immediately be an acceptable addition to the lineup or rotation. You can count on one hand the list of big contracts that failed to meet that standard.
So it’s quite surprising when two of those contracts contain the same terms and involved players originally from the same team.
The 2019 Washington Nationals’ dilemma was doomed from the start
Dec. 30, 2025, saw the arrival of news that seemed inevitable for years. Anthony Rendon and the Los Angeles Angels have reportedly agreed to a buyout of the final year of his contract in 2026, paving the way for the third baseman to retire at the age of 35.
Rendon spent all of 2025 recovering from hip surgery and is still owed $38 million for 2026. It’s unclear how much of that money Rendon will receive, but it will be paid out over the course of the next three-to-five years. Because he has nearly all of the leverage in buyout talks, he likely got most of that money in exchange for freeing up some 2026 cash for club and ending an Angels career that became a distracting fiasco.
Let’s now rewind back to the end of the 2019 MLB season. The Washington Nationals had broken through for their first World Series title, featuring an array of veterans and young stars. As they entered the offseason, they had two clear items at the top of their to-do list: Re-sign Rendon and World Series MVP Stephen Strasburg.
It was a tough decision. Rendon, at the time, was one of the best third basemen in MLB and theoretically a better long-term bet, despite past injury issues. He had just slashed .319/.412/.598 while leading the NL in doubles (44) and RBI (126). He had also played at least 130 games the previous four seasons.
Strasburg, meanwhile, had just posted the best season of his career and had the emotional factor of being the first overall draft pick who marked the beginning of the Nationals’ new era. He had been a face of the franchise since he was selected in 2009 and had just led the NL with 209 innings pitched while displaying his usual post-Tommy John surgery effectiveness.
The Nationals would’ve liked to retain both players but ultimately reached an agreement with only Strasburg, for seven years and $245 million. Coincidentally, those were the same terms Rendon agreed to with the Angels only two days later.
With the benefit of hindsight, it is now clear that the ideal outcome for Washington would’ve been signing neither of them. Because the identical deals turned out to be arguably the worst deals any MLB team has ever made from a financial perspective.
Only one other contract compares to Anthony Rendon’s and Stephen Strasburg’s
Let’s keep this simple. Here is Baseball Reference’s list of the 50 largest contracts in MLB history, with deals going back to 2001. It includes both free-agent contracts and extensions.
At the top end is Juan Soto’s record 15-year, $765 million deal with the New York Mets. At the bottom end is Matt Olson’s eight-year, $168 million extension with the Atlanta Braves.
Among those 50 players, Rendon ranks 41st in Baseball Reference’s calculation of Wins Above Replacement, and Strasburg is 46th. That doesn’t sound extravagantly disastrous, but consider that three of the deals (Cease, Vladimir Guerrero Jr. and Garrett Crochet) haven’t started yet, so those ranks are actually out of 48 players. And it takes only one good season — such as Max Fried’s 2025 — to rank 39th, where Fried is now.
Then consider that of the five non-Strasburg players below Rendon, three signed their deals in the past two years: Willy Adames, Aaron Nola and Corbin Burnes. It’s far too early to judge them.
That basically leaves two candidates to compare with Rendon and Strasburg for the worst ever: Miguel Cabrera’s eight-year, $240 million extension with the Detroit Tigers and Kris Bryant’s seven-year, $182 million deal with the Colorado Rockies.
At the risk of hand-waving, we can at least say Cabrera had a Silver Slugger-level year in 2016, the first year of that contract, and he’ll go into the Hall of Fame as a Tiger. The Tigers could’ve spent that money more wisely, yes, but Cabrera doesn’t fit in with this group.
That means that among the 50 largest MLB contracts ever, we’re left with Rendon, Strasburg and Bryant as the least rewarding from a financial standpoint, team-wise. All three are players who got enormous paydays — even bigger than Chris Davis’ infamous seven-year, $161 million deal, which might have been the previous low-water mark as far as value — and simply failed to stay on the field with any regularity.
In the case of Rendon, you have a player who started well — but only in the COVID-shortened 2020 season, in which he slashed .286/.418/.497 in 52 games. Since then, well, he still has yet to play more than 60 games in a season with the club while slashing .231/.329/.336 in 205 games from 2021 to 2025. There was a season-ending hip injury in 2021, a nearly season-ending wrist injury in 2022, a season-ending fractured tibia in 2023, a hamstring tear and oblique injury in 2024, and the hip surgery in 2025.
Strasburg was even more injury-ravaged. Following that 2019 season in which he led the NL in innings pitched, he made seven starts total, across which he posted a 6.89 ERA. That’s worth repeating: seven starts, or the number a pitcher usually makes over the course of less than two months. He experienced a nerve issue in his pitching hand in 2020, then was diagnosed with thoracic outlet syndrome (TAS) in 2021. There might not be a more dreaded issue for a pitcher than TAS, from which successful returns are few and far between. Strasburg never adequately recovered and retired after negotiating a buyout last year.
Bryant’s contract was odd from the start. When the Rockies signed him, he was being sold as a middle-of-the-order bat who could play five different positions. Colorado, in its finite wisdom, decided he should instead be a full-time left-fielder. Like Rendon, the first year was fine when he was on the field, with a .306/.376/.475 slash line in 2022, but back and foot issues limited Bryant to 42 games.
Since then, Bryant has been barely playable in 128 games across three seasons and was diagnosed with a degenerative disc disease in May. If he plays a full season again, it will be a surprise. Like with Rendon, there are rumors Bryant has played his final game, though he recently insisted he’s not contemplating retirement.
How do you compare these three? That’s ultimately up to you, but let’s say Strasburg is the worst because, again, the Nationals ended up paying nearly that entire $245 million for seven overall bad starts. And the contract was reportedly not insured, so they were on the hook for the full sum minus whatever they saved in the buyout. Rendon and Bryant had similar arcs with good-but-limited first seasons and then a full injury breakdown, with Rendon playing 205 games in five seasons and Bryant playing 128 games in three seasons.
Now let’s consider two things. One, Rendon’s contract was $63 million more expensive overall, which ain’t nothing. Two, while Bryant has by all accounts been committed to coming back, Rendon has been blasé about his baseball future to an infamous degree. He said baseball wasn’t his top priority in 2024 and has shrugged off attempts by reporters at a status check-in. There was also that 2023 incident in which he took a swing at an opposing fan.
In other words, Rendon has barely played since 2020, hasn’t played well at all since 2020 and has played a central role in the Angels becoming the complete laughingstock they are now. To us, that sounds like a contract worse than Bryant’s, even if the latter is worse by total WAR.
As for other candidates, there are deals such as Davis and Ryan Howard, who got their paydays and simply ceased to be replacement-level players, but they at least stayed on the field. There’s also Josh Hamilton, whose disappointing Angels tenure ended two seasons in after he unfortunately relapsed with his addiction issues. But that’s a very difficult comparison for these purposes, especially when his contract came in tens of millions of dollars less than the three discussed here.
This is all admittedly harsh. None of these players has control over their health and to judge a person by the ratio of their labor to their cost is inherently dehumanizing. These were all good players at one point, and all three have well-deserved World Series rings. They just also happen to be major reasons so many fans get antsy when their teams actually commit to spending in free agency.
So congratulations, 2019 Nationals. You will be remembered for reasons beyond a cathartic World Series title. And those reasons are now beyond mitigation.