Ranking MLB’s Ugliest Contracts in 2025: Worst Underwater Deals

This article digs into the worst MLB contracts heading into 2025. Injuries, age, and decline have turned once-celebrated deals into financial headaches.

The Los Angeles Dodgers thrive with smart spending and elite depth. Meanwhile, plenty of other clubs feel handcuffed by massive guarantees owed to stars who just aren’t producing anywhere close to their paychecks.

The Contrast: Dodgers’ Precision vs. League-Wide Contract Nightmares

The Dodgers set the modern standard for roster construction. They’ve got deep pockets, but they also make tough calls and keep churning the roster.

They don’t let sentiment dictate payroll. Elsewhere, a bunch of marquee names have become a graveyard of sunk costs.

Long-term contracts that once looked like franchise-defining moves now weigh down flexibility. Future planning gets a lot harder with those deals on the books.

Anthony Rendon: The Gold Standard of Bad Contracts

No contract sums up this problem better than Anthony Rendon’s deal with the Los Angeles Angels. Rendon was once a World Series hero and elite two-way third baseman.

Now, he’s the league’s cautionary tale. Rendon missed the entire 2025 season after hip surgery, and the Angels still owe him about $27 million a year for two more years.

That’s superstar money for zero value on the field. Injuries and an inability to stay healthy have turned what was supposed to be a cornerstone contract into a financial anchor for a franchise already struggling to build around its stars.

Kris Bryant and the Rockies’ Painful Gamble

The Colorado Rockies took a huge swing signing Kris Bryant, hoping his MVP pedigree would stabilize their lineup. Instead, Bryant’s body just hasn’t held up.

In 2025, Bryant played only 11 games. Injuries and chronic back problems have defined his time in Denver.

When your big free-agent splash barely takes the field, the contract turns from hopeful investment to an albatross. It makes any kind of meaningful rebuild feel almost impossible.

Houston’s High-Risk Core: Big Names, Bigger Concerns

The Houston Astros have been one of the era’s great success stories. Still, a few hefty deals on their books now look like long-term liabilities.

Injuries and regression are hitting at the same time. That’s raising real questions about their payroll structure.

Christian Walker, Carlos Correa, and Lance McCullers Jr.

Each of these players arrived with star-level production or postseason pedigree. But the on-field results haven’t matched the checks being cut.

• Christian Walker hasn’t delivered the consistent middle-of-the-order impact his contract promised.
• Carlos Correa used to be a dynamic two-way shortstop, but his performance and availability have both slipped.
• Lance McCullers Jr. keeps battling injuries, so his big contract feels risky for a team that needs reliable innings.

Position Players Failing to Match Their Paydays

Across the league, several everyday players get paid like stars but play more like role guys. That gap between salary value and on-field value is where contracts really go off the rails.

Benintendi, Bogaerts, and Nola: Underwhelming Returns

Andrew Benintendi has become a problem for the Chicago White Sox. He was supposed to bring stability and on-base skills, but his production has been middling at best.

Xander Bogaerts with the San Diego Padres is another example. Age, defensive regression, and less offensive punch have made this long-term deal look questionable already.

On the mound, Aaron Nola of the Philadelphia Phillies hasn’t really lived up to his big salary. He still shows flashes, but the inconsistency and lack of ace-level dominance make his contract look steep.

Darvish and Rodríguez: Pitching Investments Gone Sideways

Big-name pitchers always carry big risk, and both Yu Darvish and Eduardo Rodríguez prove that. Injuries and stretches of ineffectiveness keep popping up for both guys.

When a top-of-the-rotation arm doesn’t deliver, the financial strain gets magnified fast.

Big Market Misfires and Mid-Market Miscalculations

Even the big-money franchises—and those clawing for contention—are feeling the sting from bad deals. Sometimes it’s performance, sometimes it’s timing, sometimes just bad luck.

Yankees, Tigers, Blue Jays, and Rangers in the Crosshairs

Giancarlo Stanton of the New York Yankees still has that raw power. But long stretches of inconsistency and health issues mean New York pays superstar money for only occasional impact.

The Detroit Tigers are stuck with Jeimer Candelario (Báez) on a pricey deal that hasn’t delivered. For a club not yet over the hump, that kind of dead weight on the payroll is especially tough.

In the AL East and AL West, Jorge Santander of the Toronto Blue Jays and Joc Pederson of the Texas Rangers haven’t justified their big contracts. Injuries and underperformance have turned these moves into cautionary tales.

Mike Trout: Greatness in a Losing Context

Mike Trout is a different kind of contract dilemma. He’s still a productive, elite-caliber player, and by the numbers, his deal is more defensible than most here.

But the Angels have no clear path to contention, and Trout’s massive salary eats up a huge chunk of the payroll. In isolation, his contract isn’t “bad,” but when you factor in age, injuries, and the franchise’s lack of direction, it’s another example of how even a great player can be part of a messy financial picture.

The Bigger Picture: Balancing Star Power and Financial Risk

These contracts really highlight something obvious but important: MLB teams are always trying to balance chasing big names with not getting stuck in financial quicksand. If a massive contract actually works out, it can keep a team competitive for ages.

But when it flops, it can totally stall a rebuild and back teams into tough corners. Flexibility disappears, and suddenly, decisions get a lot harder.

The Dodgers keep showing how smart, numbers-based spending can work wonders. Every offseason, the rest of the league seems to circle back to the same old question: how do you pay for the stars you need now without wrecking your future?

Honestly, in 2025, a lot of teams are realizing—sometimes painfully—that there’s just no simple fix.

 
Here is the source article for this story: What’s the ugliest contract in MLB? Ranking baseball’s worst underwater deals