Big money MLB contracts look smart on the first press conference day. In 5 years, a few of these deals could feel like concrete shoes on a payroll.
The very biggest MLB contracts are not just about talent. They are about belief. Front offices lock in 9, 10, even 11 years of commitment and say, out loud and in dollars, that this player will still be worth it when the speed fades and the aches multiply.
This list looks at MLB contracts that could age badly over the next 5 years. Not because the players are bad. Many are still stars. But the combination of age, health, length, and sheer size turns these deals into real financial stress tests for their clubs.
Context: Why Risky Deals Matter
There is no escape hatch if a player stops being a star before the money stops landing in his account.
Front offices accept that risk when they sign long contracts. They know they are paying for prime seasons at the front, and they may eat dead money at the back. The tension shows up when the decline starts earlier than expected, or when injuries turn a superstar into a part time starter.
Over the next 5 years, a handful of MLB contracts sit right on that fault line. They tie up eight figure annual salaries at ages and positions where decline is common. They press against the Competitive Balance Tax and crowd out future moves. And they test how far an owner is willing to go before saying, quietly, that a contract has become a problem.
These rankings draw on public contract databases like Spotrac and Cot style research, performance metrics such as WAR and OPS plus, injury history, aging curves and roster context, with ties broken by total guaranteed money and years left instead of any era based adjustments.
The Risky Money On The Books
1. Manny Machado And Risky MLB Contracts
The defining moment came in spring 2023, when Manny Machado and San Diego agreed on a 11 year, 350 million extension that runs through 2033. The Padres were coming off a deep playoff run, the ballpark buzzed every night, and ownership decided to push all their chips toward a long window with Machado, Fernando Tatis Jr, and a wave of expensive stars.
On paper, the early value has already slipped from his near MVP peak. From 2018 through 2022 he played at a clear superstar level, often sitting above 5 WAR. The last couple seasons have landed in a lower tier, closer to solid regular than top five position player. By the time this deal hits the final 5 years, he will be in his mid 30s, still pulling more than 30 million a season while the club tries to rebuild a thin farm and a top heavy payroll.
Emotionally, this contract is tied to a whole era in San Diego. Machado is the face of the swagger the Padres sold, for better and worse. When he said, “In my mind, I was always going to be a Padre,” it sounded like a love story between player and city. If the back half of the deal turns into dead money, that same line will read more like a warning about how long you should tie yourself to any player.
Behind the scenes, people around the club talk about how often younger players still watch how Machado moves and talks in the clubhouse. That is leadership, but it is also pressure. If his body drifts further from his prime while the salary stays at full star rate, every free agent the Padres choose not to sign in the next 5 years will be viewed through the lens of this extension.
2. Xander Bogaerts Bet That May Hurt
In December 2022, the Padres doubled down again and handed Xander Bogaerts a 11 year, 280 million deal that also runs through 2033. It felt wild in the moment, dropping another nine figure contract on a roster that already had Machado and Tatis paid like franchise anchors.
The baseball problem is simple. His offensive numbers dipped well below his Boston peak, and the Padres have already begun to shuffle him off shortstop to make the defense work. Compared with other long term shortstop deals, like Corey Seager in Texas or Francisco Lindor in New York, Bogaerts has delivered fewer wins so far on a similar financial footprint.
The vibe around this contract shifted fast. At first it looked like a bold move from a small market club flexing like a coastal giant. Now it feels more like a weight that drags every trade rumor and free agent story back to the same question: how many high priced veterans can one mid market payroll carry at once.
3. Kris Bryant And Sinking MLB Contracts
Look, maybe I am reading too much into this, but the Kris Bryant deal already feels like a case study that every future front office will use in “what not to do” meetings. In March 2022, the Colorado Rockies gave him a 7 year, 182 million contract to be their middle of the order star through 2028.
The numbers have been rough. Through his first three full seasons with Colorado, he has spent more time on the injured list than in the heart of the lineup, with multiple stints for foot, back, and oblique issues. His OPS has sagged well below his peak with the Cubs, and the defense has slipped from passable third base work to corner outfield and first base duty. There is still real money left, with three expensive seasons remaining and limited signs that he can get back near his early career MVP level.
Fans in Denver feel that weight.Instead, “Why did they give Bryant that money” has become almost its own sport talk segment. Around the league, analysts now group his deal with the worst long term commitments on any roster.
The small personal details make it sting more. Bryant talked at his press conference about loving the city and wanting his young family to grow up there. He smiled and joked with his son on the stage. In 5 years, if the contract is remembered mostly as a sunk cost that blocked a reset, that first happy day is going to look very different in hindsight.
4. Mike Trout And Aging MLB Contracts
You know the story here. The Los Angeles Angels signed Mike Trout to a 12 year, 426.5 million extension in 2019, locking in one of the best players anyone has ever seen through his age 38 season. It was the sort of deal you give when you think you are paying for a living legend and a long line of playoff runs.
Since 2021, the injuries have piled up. Trout has missed huge chunks of multiple seasons with calf, back, knee, and wrist issues, and the Angels have already moved him from center field to right field to reduce the wear on his body. In the last few years he has played barely more than a full season total while still carrying an annual salary in the mid 30 million range. Compared with his own early peak, his WAR and plate appearances have fallen off a cliff. Yet the contract still ranks near the top of MLB in total value with 5 seasons to go.
Trout has tried to push back on any trade talk. At one point he said, “I want to win a championship here,” and you believed him. If the Angels remain stuck in neutral while paying prime money for partial seasons, the question in 5 years will not be about what he did in his twenties. It will be about how long a small window of greatness can justify a decade plus of financial squeeze.
5. Wander Franco Deal In Limbo
Some contracts become headaches because of age or injury. Wander Franco’s monster extension with Tampa Bay turned into something else entirely. In late 2021, the Rays signed him to a 11 year, 182 million guarantee with a club option that could push the total past 220 million. It was the largest deal in team history and one of the biggest ever for a player with so little service time.
On the field, the early returns were strong. Franco flashed star level production at shortstop and made an All Star team by age 22. But his career stopped in 2023 when allegations surfaced about a relationship with a minor. He was placed on administrative leave, then moved to the restricted list without pay once formal charges were filed. In June 2025 a Dominican court found him guilty of sexually abusing a minor and handed him a suspended prison sentence, while MLB kept him off the field and under investigation.
Behind the scenes, people in the game talk about Franco as a cautionary tale for pre arbitration mega deals. No front office can fully guard against off field behavior, but the size and length of this extension make the loss more than just a baseball issue. In 5 years, whatever the final legal outcome, this contract will still be cited as one of the most painful miscalculations any team has made.
6. Trea Turner Bet On Speed
In winter 2022, the Philadelphia Phillies pushed their chips in on Trea Turner with a 11 year, 300 million contract that runs through 2033 and includes a full no trade clause. It was a huge bet that his rare blend of speed, defense, and power would carry deep into his thirties.
The stat line so far has been a roller coaster. His first season in Philadelphia started with a slump so deep that fans organized a standing ovation to lift him up, and it worked. He raked from August on, and by 2025 he had turned in a 6.7 WAR season, won the National League batting title with a .304 average, and finished in the top tier of NL position players again. The problem is not present day value. It is what happens when his game, built on speed, has to survive ages 34 to 39 at more than 27 million per season.
From a culture standpoint, the bond between Turner and Phillies fans is real. That standing ovation night is already Philadelphia lore, complete with a documentary and an Emmy. The city chose to cheer a struggling star rather than boo, and he rewarded them. That buys a lot of patience, but it does not erase the back half of the contract.
7. Jacob DeGrom Contract On A Knife Edge
Here is the thing about Jacob DeGrom. When the Texas Rangers handed him a 5 year, 185 million contract before the 2023 season, they knew they were buying both risk and greatness. He made only 6 starts in year one before needing another Tommy John surgery, then missed most of 2024.
The comeback in 2025 has been a reminder of why they did it. DeGrom returned to throw more than 170 innings with a sub 3 ERA, won Players Choice Comeback Player of the Year, and even became the fastest pitcher on record to reach 1,700 strikeouts. At age 37 he still sits near the top of the league in run prevention when healthy. The fine print is cruel though. He is owed roughly 40 million per season through 2027, with a conditional option that could push the total value past 220 million if he keeps performing at a Cy Young level. One more serious elbow or shoulder issue could turn those last seasons into pure sunk cost.
Fans have mostly stayed on his side. His first start back at Citi Field in a Rangers uniform turned into a long standing ovation. Mets supporters and Rangers fans both treated it like a shared moment, not a betrayal. That does not change the math for Texas if his body breaks again.
What Comes Next
Think about it this way. Every massive MLB contract is a story about time, money, and how long a body can fight the curve.
Over the next 5 years, front offices will watch these deals and decide what lessons to take. Here is the quiet question that hangs over all of it.
When does loyalty to a star stop being love for a player and start being fear of admitting a contract was a mistake.
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I bounce between stadium seats and window seats, chasing games and new places. Sports fuel my heart, travel clears my head, and every trip ends with a story worth sharing.
