Imagine this: your favorite MLB team just signed a star player to a massive contract, and fans are ecstatic. But fast forward a few years, and that same deal is now a millstone around the team's neck. Welcome to the world of free agency gone wrong, where bad contracts can haunt franchises for years. But here's where it gets controversial: are these deals simply unfortunate missteps, or do they reveal deeper issues in how teams evaluate talent and manage their finances? Let's dive into some of the most notorious MLB free agency contracts that are still causing headaches in 2026—and explore why they're so hard to escape.
Eduardo Rodriguez, Arizona Diamondbacks
When the Arizona Diamondbacks signed left-handed pitcher Eduardo Rodriguez to a four-year, $80 million deal, it seemed like a steal. After all, Rodriguez had just posted a 3.30 ERA in his final season with Detroit, showcasing a deceptive low-90s fastball and a strong five-pitch mix. But here’s the part most people miss: his expected ERA that season was 4.07, a glaring red flag that Arizona—like many others—overlooked. Fast forward to 2026, and Rodriguez is still owed $21 million this year, $19 million in 2027, and a mutual option of $17 million in 2028. After missing most of 2024 due to injuries and posting a 5.02 ERA in 2025, his prime years feel like a distant memory. At 33, with declining velocity, a return to form seems unlikely. Arizona’s front office is now stuck, unable to invest heavily in pitching while this contract lingers.
Anthony Rendon, Los Angeles Angels
Anthony Rendon’s seven-year, $245 million deal with the Los Angeles Angels in 2020 was supposed to make him Mike Trout’s superstar sidekick. Instead, it became one of the most crippling contracts in baseball. After restructuring his deal in 2026, Rendon’s $38 million salary was spread over five years, effectively ending his tenure in L.A. But the damage was done. Rendon’s production plummeted, and the Angels were left with a financial black hole that prevented them from competing in the postseason. The team is now treading water, much to the frustration of fans who want to see Trout in meaningful games. And this is the part most people miss: Rendon’s contract wasn’t just bad—it was a symptom of the Angels’ broader inability to build a winning roster.
Anthony Santander, Toronto Blue Jays
At first glance, Anthony Santander’s five-year, $92.5 million contract with the Toronto Blue Jays doesn’t look terrible, especially with a $13.5 million signing bonus softening the annual cap hit. But after a disastrous 2025 season where he played just 54 games with a .565 OPS, the deal feels far less appealing. What makes it worse? The Blue Jays narrowly missed out on Kyle Tucker, who signed with the Dodgers instead. While Santander could rebound—he did hit 44 home runs in 2024—he’s now on the wrong side of 30, and his value hinges on his power. If Tucker thrives in L.A. while Santander continues to struggle, Blue Jays fans will have a hard time forgiving this missed opportunity.
Masataka Yoshida, Boston Red Sox
The Boston Red Sox’s five-year, $90 million investment in Masataka Yoshida looked promising after his rookie season, with a .783 OPS across 140 games. But his performance has declined sharply since, with a .696 OPS in 2025 and recurring injury issues limiting him to just 55 games. Yoshida’s lack of versatility—he’s almost exclusively a DH—and his diminishing power make him a liability. Boston’s surplus of outfielders means there’s no room for him in the lineup, and his trade value is virtually nonexistent. The Red Sox would undoubtedly love a do-over, but they’re stuck with a player who complicates their roster and payroll.
Xander Bogaerts, San Diego Padres
Xander Bogaerts’ 11-year, $280 million contract with the San Diego Padres in 2023 felt like a bold move at the time. But in 2026, it’s looking like a massive overcommitment. While Bogaerts is still a solid player—with a .720 OPS and improved defense in 2025—he’s 33, and his offensive decline is undeniable. The Padres will be paying him over $25 million annually into his 40s, a commitment that’s already hindering their ability to sign younger, more impactful players. With ownership disputes and a depleted farm system, San Diego is stuck in neutral, and Bogaerts’ contract is a big reason why.
Carlos Correa, Houston Astros
The Houston Astros’ reunion with Carlos Correa at the 2025 trade deadline was a desperate move that backfired spectacularly. Despite his solid .734 OPS last season, Correa is now 32, and his $20 million-plus salary through 2032 feels excessive. The Astros are forced to consider trading Isaac Paredes, a younger and more productive player, just to accommodate Correa’s contract. This deal has thrown their roster construction into disarray, leaving fans to wonder: was bringing back Correa worth sacrificing the team’s future flexibility?
Aaron Nola, Philadelphia Phillies
Aaron Nola’s seven-year, $172 million extension with the Philadelphia Phillies in 2024 seemed like a no-brainer at the time. But after a disastrous 2025 season with a 6.01 ERA, the deal now looks like a costly mistake. While Nola’s injuries last season weren’t to his arm, the fact remains that older pitchers rarely get healthier. His contract has already limited the Phillies’ ability to pursue other stars, like Bo Bichette, and contributed to Ranger Suárez’s departure. With Zack Wheeler injured, Philadelphia’s rotation is suddenly a question mark, and Nola’s deal feels like an anchor.
The Bigger Question
These contracts aren’t just financial burdens—they’re cautionary tales about the risks of long-term deals in a sport where performance can decline rapidly. But here’s the controversial part: are teams too focused on past performance when evaluating players, or are they failing to account for factors like age, injury history, and positional versatility? And what does this say about the pressure on front offices to make splashy signings, even when they might not be the smartest move?
What do you think? Are these contracts simply unlucky, or do they reveal deeper flaws in how teams approach free agency? Let’s debate it in the comments!
