There is always a significant level of risk involved when it comes to handing out massive contracts in MLB free agency, and that will no doubt be on the minds of teams kicking the tires on the market's top-tier players once again this winter.

While many of the most obvious ill-advised long-term deals have come and gone, including the end of Patrick Corbin's contract with the Washington Nationals this offseason, there are still a handful of notable ones on the books heading into the 2025 season.

Ahead, we've ranked the 10 worst contracts that teams are stuck with going forward, focusing on players with multiple years remaining on their current deal. The deals were ranked based on remaining money owed, recent production and expected production going forward.

No contracts with one year remaining were considered, since the finish line is in sight on them and teams can more easily navigate them as a result.

10. All the Bad Contracts With 2 Years Remaining

Remaining years and money left on the books is a major factor in deciding which contracts rank as the worst heading into the new season, so it seemed reasonable to lump all of the bad deals with two years left on the books into one category in the No. 10 spot.

Here are the worst deals with only two years remaining and a light at the end of the tunnel:

3B Anthony Rendon, LAA: Two years, $77.1 million
SP Robbie Ray, SF: Two years, $50 million
OF George Springer, TOR: Two years, $48.3 million
OF Nick Castellanos, PHI: Two years, $40 million
SP Taijuan Walker, PHI: Two years, $36 million
SP Lance McCullers Jr., HOU: Two years, $35.4 million
IF DJ LeMahieu, NYY: Two years, $30 million
1B/3B Jeimer Candelario, CIN: Two years, $29 million

The worst of the bunch is undoubtedly Anthony Rendon, who has managed just 4.7 WAR over the first five seasons of his seven-year, $245 million deal and will again be one of the highest-paid players in the sport in 2025.

Further down the list, Taijuan Walker and DJ LeMahieu are both candidates to be outright released this offseason as a sunk cost could outweigh their negative contributions.

On the flip side, a healthy Robbie Ray could be a major X-factor for the San Francisco Giants, while George Springer is not far removed from being an All-Star-caliber player and could bounce back with a better supporting cast.

9. OF Andrew Benintendi, Chicago White Sox

Remaining Contract

2025: $17.1 million
2026: $17.1 million
2027: $15.1 million

Total Remaining Money: $49.3 million

Among 129 position players who recorded enough plate appearances to qualify for the batting title, Andrew Benintendi ranked 128th with minus-0.8 WAR in the second season of a five-year, $75 million contract.

The 30-year-old was coming off a career year and his first All-Star selection when he signed that contract, but that level of production has been nowhere to be found since he joined the Chicago White Sox, and now he is on an albatross contract for a team at rock bottom of a rebuild.

Benintendi hit .229/.289/.396 for a 95 OPS+ with 20 doubles and 20 home runs in 522 plate appearances this past season, and the former Gold Glove defender was also one of the worst defensive players in baseball (-13 DRS, -1.4 UZR/150) in left field.

8. OF Christian Yelich, Milwaukee Brewers

Remaining Contract

2025: $26 million
2026: $26 million
2027: $26 million
2028: $26 million

Total Remaining Money: $104 million

After winning the 2018 NL MVP and finishing runner-up in the balloting the following year with a second straight 7-WAR season, Christian Yelich inked a nine-year, $215 million extension with the Milwaukee Brewers.

His production cratered during the shortened 2020 season, and he tallied just 4.3 WAR over the first three seasons of that shiny new contract, but he has returned to being an impact offensive player the last two years.

The 32-year-old was an All-Star this past season for the first time since 2019, hitting .315/.406/.504 for a 151 OPS+ in 315 plate appearances before undergoing season-ending back surgery in August.

For a team like the Brewers on a tight budget, having Yelich account for more than 30 percent of their $70.8 million payroll in 2024 was simply too big of a piece of the pie. That will continue to be the case in the coming years.

7. DH Giancarlo Stanton, New York Yankees

Remaining Contract

2025: $32 million
2026: $29 million ($10 million paid by MIA)
2027: $25 million ($10 million paid by MIA)

Total Remaining Money: $86 million ($20 million paid by MIA)

Giancarlo Stanton put together a fantastic 2024 postseason for the New York Yankees, posting a 1.048 OPS with seven home runs and 16 RBI in 14 games and taking home ALCS MVP honors.

That said, the 35-year-old is no longer the star-caliber player he was in his prime, and while he continues to provide over-the-fence power, he has tallied a combined 0.6 WAR in 325 games over the past three seasons.

His strong playoff performance and the fact that the Marlins are on the hook for roughly 25 percent of his remaining salary keeps him from ranking any higher, but it's unlikely he will live up to his salary over the remaining three seasons of his 13-year, $325 million megadeal.

6. SS Trevor Story, Boston Red Sox

Remaining Contract

2025: $22.5 million
2026: $25 million
2027: $25 million

Total Remaining Money: $72.5 million

Trevor Story has played just 163 games over the first three seasons of his six-year, $140 million deal with the Boston Red Sox, hitting .232/.296/.397 for an 89 OPS+ with 21 home runs, 90 RBI and 4.0 WAR during that span.

A shoulder issue and subsequent surgery limited him to a career-low 26 games in 2024, and with top prospects Marcelo Mayer and Kristian Campbell knocking on the door, the Boston front office could start looking to cut its losses in the not-too-distant future.

After racking up 26.8 WAR, two All-Star selections and two Silver Slugger Awards during his six seasons with the Colorado Rockies, Story has been a complete non-factor over the first half of his Red Sox contract, and at 32 years old, a return to his peak form seems increasingly unlikely.

5. SP Jacob deGrom, Texas Rangers

Remaining Contract

2025: $40 million
2026: $38 million
2027: $37 million

Total Remaining Money: $115 million

The Texas Rangers have paid Jacob deGrom a staggering $70 million for nine starts and 41 innings of work over the first two seasons of his five-year, $185 million contract, and he was watching from the sidelines during their 2023 World Series run.

The 36-year-old did return with a 1.69 ERA and a 14-to-1 strikeout-to-walk ratio in 10.2 innings over three late-season starts, and a clean bill of health heading into the offseason will be a welcome change for the two-time Cy Young winner.

However, the Rangers are now in a transition period following a disappointing 2024 campaign, and having $115 million still on the books does not aid in their efforts to get below the luxury-tax threshold.

4. 2B/SS Xander Bogaerts, San Diego Padres

Remaining Contract

2025: $25.5 million
2026: $25.5 million
2027: $25.5 million
2028: $25.5 million
2029: $25.5 million
2030: $25.5 million
2031: $25.5 million
2032: $25.5 million
2033: $25.5 million

Total Remaining Money: $229.5 million

The San Diego Padres' decision to sign Xander Bogaerts to an 11-year, $280 million deal during the 2022-23 offseason was a bit of a head-scratcher from the start, especially considering the longstanding belief he would likely have to shift off shortstop in the not-too-distant future.

After a 4.4-WAR debut with the team in 2023, he had one of the worst seasons of his career in 2024, hitting a punchless .264/.307/.381 for a 92 OPS+ and tallying just 1.2 WAR in 111 games—his lowest total since his rookie season in 2014.

The 32-year-old also shifted to second base last spring, opening up the shortstop position for a superior defender in Ha-Seong Kim, but now Kim is departing in free agency and Bogaerts may be forced to make a full-time return to a position where he logged below-average defensive metrics (-4 DRS, 0.0 UZR/150) in 2023.

He will be 40 years old in the final season of his contract, and while a rebound from his 2024 performance is not out of the question, the general downward trajectory of his form is likely to continue.

3. SS Javier Báez, Detroit Tigers

Remaining Contract

2025: $25 million
2026: $24 million
2027: $24 million

Total Remaining Money: $73 million

At his peak with the Chicago Cubs, shortstop Javier Báez was one of the most dynamic players in baseball, making back-to-back All-Star appearances and finishing runner-up in 2018 NL MVP balloting on the strength of his power, speed and elite defense.

After joining the New York Mets as a two-month rental at the 2021 trade deadline in a deal that sent Pete Crow-Armstrong the other way, he signed a six-year, $140 million contract with the Detroit Tigers in free agency and was expected to be a cornerstone of their rebuilding efforts.

Instead, the 31-year-old has hit an unsightly .221/.262/.347 for a 71 OPS+ in 1,426 plate appearances over the first three years of that deal, and his already diminished production cratered in 2024 when he hit .184 with a 46 OPS+ in 289 plate appearances before undergoing season-ending hip surgery.

In his absence, rookie Trey Sweeney showed legitimate upside as the starting shortstop, and Báez will now need to earn his playing time in a platoon role to start the 2025 campaign.

2. OF Kris Bryant, Colorado Rockies

Remaining Contract

2025: $27 million
2026: $27 million
2027: $27 million
2028: $27 million

Total Remaining Money: $108 million

Few players have had a better start to their MLB career than Kris Bryant, who won 2015 NL Rookie of the Year and followed it up with 2016 NL MVP honors while helping the Chicago Cubs break a 108-year title drought.

He was a four-time All-Star during his seven seasons with the Cubs, including the 2021 season when he was traded to the San Francisco Giants at the deadline ahead of his first foray into free agency.

Bryant ultimately signed a seven-year, $182 million deal with the Colorado Rockies, who were seemingly bidding against themselves at that asking price and were by no means one splashy signing away from being contenders.

That contract now looks like a legitimate contender to go down as the least productive $100 million deal ever handed out, as injuries have limited him to 159 games and minus-1.3 WAR over his first three years in Colorado.

The 32-year-old played 37 games and hit .218/.323/.301 with two home runs in 155 plate appearances in 2024.

1. OF Mike Trout, Los Angeles Angels

Remaining Contract

2025: $37.2 million
2026: $37.2 million
2027: $37.2 million
2028: $37.2 million
2029: $37.2 million
2030: $37.2 million

Total Remaining Money: $223.2 million

Let's start by saying that if Mike Trout retired tomorrow, he would be a first-ballot Hall of Famer in five years.

The 33-year-old is an 11-time All-Star, three-time MVP winner and was on an all-time great trajectory over the first 10 seasons of his career when he piled up 74.3 WAR and was one of the faces of baseball.

However, he has played in just 266 of 648 games over the past four seasons, which amounts to nearly 60 percent of the time spent watching from the sidelines.

A nagging back injury was the most glaring issue at the start of that injury-plagued stretch, though it was a torn meniscus in his left knee and then a second tear of the same meniscus later in the year that limited him to just 29 games in 2024.

He is still capable of making an impact when healthy, evidenced by his 140 OPS+ and 10 home runs in 126 plate appearances when he was able to take the field this past season, but the injury woes are starting to pile up.

Trout's contract is essentially immovable at this point, leaving an Angels team that is in serious need of a roster retooling to continue trying to build around its aging superstar and his bloated salary.