Top 6 MLB contract blunders set to haunt front offices in 2026 ft. Yu Darvish

The MLB offseason has already witnessed a blockbuster deal after the Toronto Blue Jays signed free agent ace Dylan Cease on a franchise record seven-year $210 million deal in November.

While Cease was among the most coveted starting pitchers in free agency, only time will tell if he could prove his worth in Toronto and live to the expectations that comes with signing a record deal.

With teams likely to go big on the remaining top talents this offseason, we list some of the biggest deals to have backfired for MLB teams.

Javier Baez - Detroit Tigers

Baez signed a six-year, $140 million contract with the Detroit Tigers in December 2021. While the Tigers expected Baez to be the franchise cornerstone, the former NLCS MVP failed to live up to the expectations.

After the first three seasons in Detroit, Baez posted a .516 OPS and -1.1 rWAR, raising questions about his future with the team. While many believed he would be released by the Tigers, Baez turned things around in the first half of the season in 2025 to earn his first All-Star selection since 2019.

However, the three-time All-Star slumped in the second half, proving his six-year contract was one of the biggest blunders in MLB history.

Masataka Yoshida - Boston Red Sox

Yoshida was posted for MLB teams in December 2022 and the Red Sox went big by signing the Japanese outfielder on a five-year deal worth $90 million. While Yoshida showed early promise, his tenure has not been what Red Sox fans would've expected.

He underwent shoulder surgery in October last year and missed most of the first half of the 2025 season. He batted .266 in 55 games with four home runs and three stolen bases. He has two years remaining on his contract and the Red Sox could ship him off this offseason.

Lance McCullers Jr. - Houston Astros

The Astros turned a few heads after they offered a five-year, $85 million contract extension to Lance McCullers Jr. in 2021 after an injury riddled 2020 season.

McCullers Jr. lived up to the expectations in the 2021 season, making 28 starts and posted a 3.16 ERA with 185 strikeouts over 162.1 innings. However, injuries have derailed his career since,

After missing the entire 2023 and 2024 season, McCullers was added to the bullpen in the second half of the 2025 season and is expected to pitch in relief next season.

Anthony Rendon - Los Angeles Angels

When the Angels signed Anthony Rendon in 2020, they hoped for an All-Star calibre slugger to partner Mike Trout in the hitting order. Little did they know they were playing their part in one of the worst contracts in MLB history.

Rendon signed a $245 million for seven years after his World Series winning campaign with the Washington Nationals. However, it and been setback after setback for the All-Star slugger since.

Frequent injury issues and his controversial interactions with media have made Rendon a pantomime villain for Angels fans. According to reports, the 35-year-old is thinking about retirement and will opt out of the final year of his contract.

Yu Darvish - San Diego Padres

The San Diego Padres offered a $108 million contract to Yu Darvish in 2023 ahead of his age-36 season. While Darvish's ability as a top pitcher cannot be argued, the Japanese ace is not aging gracefully.

Darvish's past injuries have caught up to the All-Star pitcher as he was limited to just 31 regular-season appearances across the last two seasons. The five-time All-Star is set to miss the 2026 season due to an elbow surgery and will return for his age 40 season in 2027.

Kris Bryant - Colorado Rockies

The Colorado Rockies' $182 million contract over seven years for Kris Bryant in 2022 is arguably one of the worst deals in MLB over the last two decades. The Rockies' decision to pay Bryant a blockbuster fee in the latter stages of his career has backfired massively.

Bryant has mostly been absent because of injuries and his swing not being what it used to be in his heyday. He has played 170 games over the last four seasons with just 17 home runs.

The former NL MVP still has two years left on his contract and the way the Rockies have been sinking over the last two seasons, it seems a change could be coming for Bryant.