Ranking the 5 worst contracts in the AL East: Where do the Blue Jays land?

To be able to field a successful winning team in Major League Baseball, one of the key things is being able to sign potential impact players that can play at least to the value to their contract. However, more often than not, a team could be tied to an albatross of a contract when the player has performed below expectations, or has somehow shown signs of regression earlier than expected. As a result, it could end up affecting the overall success of the club substantially. That is because with their underperformance together with their sizeable contract, it could severely restrict a club’s financially flexibility to allow the team to look for improvements at the same time.

Among the teams in the American League East, including the Toronto Blue Jays, there are a few players that currently own one of the worst contracts in the league. Here, we will rank the five worst ones found within the division and how it has impacted their respective teams. For each candidate, the year in which the contract will finally expire appears in parentheses.

5. Masataka Yoshida, Boston Red Sox – 5 years, $90 million, $18 million AAV (2027)

As a prolific hitter coming out of the Nippon Professional Baseball (formerly the Japanese Baseball League), the Boston Red Sox signed outfielder Masataka Yoshida to a five-year deal worth $90 million during the 2022-23 offseason. With a career average of .327 and OPS of .960 while averaging 20+ home runs and 80+ RBI over a full season’s pace in seven seasons with Orix, the Red Sox believed that he could easily translate that success over to North America. 

Overall, Yoshida has performed decently so far in his two seasons with Boston, hitting .285 with a .776 OPS, along with 116 runs scored, 54 doubles, 25 home runs and 128 RBI over 248 games played. However, according to Brady Farkas of Sports Illustrated, he has already fallen out of favour in the organization this past season. The Red Sox minimized his exposure to left-handed pitching, along with utilizing him mainly in the designated hitter role despite being a more than capable outfielder, thus limiting his overall playing time as a result.

At $18 million AAV, it would seem like an overpay when compared to other designated hitters with similar salary AAV such as Yordan Alvarez of the Houston Astros and Kyle Schwarber of the Philadelphia Phillies. Both players provide close to 90+ runs scored, 35+ home runs and 90+ RBI worth of production per season, which is way beyond what Yoshida could muster in an average season.

In addition, there was even speculation that Yoshida would be moved this offseason. But with his recent labrum surgery in his right shoulder, it may have complicated things now as a result. In any event, the fact that he was no longer a necessary asset to the organization just two years into his five-year deal speaks volumes on how bad the contract must be right now.

3. DJ LeMahieu, New York Yankees – 6 years, $90 million, $15 million AAV (2026)

As one of the best pure hitters in the league during his prime, DJ LeMahieu joined the Yankees’ organization back in 2019 after signing a two-year deal with the club via free agency. LeMahieu did not disappoint as he would end up posting his career-highs in runs scored (109), home runs (26) and RBI (102) during his first season with the team.

He followed that up with a strong 2020 year in which he led the entire league in batting average (.364) and the AL in OPS (1.011), while finishing as a finalist for the AL MVP Award. On top of that, he has proven to be an elite defender in the past with three Gold Gloves under his belt previously with the Colorado Rockies. Betting on the fact that LeMahieu would continue his dominance both at the plate and in the field, the Yankees quickly locked him up for six more seasons at $15 million AAV. At the time, it seemed like a big time steal, especially with the Jays apparently in pursuit of him at the time as well.

However, LeMahieu’s numbers would fall back down to earth ever since signing his contract. In his subsequent three years, he would average just 71 runs scored, 21 doubles, 12 home runs, 49 RBI while hitting below .270 despite playing more than 125 games per season. In 2024, things had gotten even worse, as his year had been filled with injuries and inconsistency. When he was healthy, he managed only 19 runs scored, 5 doubles, 2 home runs and 26 RBI in 67 games played while batting an absymal .204 with just a .527 OPS.

With his injuries and struggles this season, along with the emergence of key players joining the roster including Jon Berti and deadline acquisition Jazz Chisholm Jr., LeMahieu gradually fell out of the rotation in the Yankees’ everyday roster. Some have even speculated that we may have seen the last of him in a Yankees’ uniform as New York will likely look to move him this offseason. But whether there will any takers after his recent injury history and regression will be another story.

2. Giancarlo Stanton, New York Yankees – 13 years, $325 million, $25 million AAV (2027)

Following his MVP season in 2017 with the Miami Marlins in which he hit a whopping 59 home runs and drove in 132 runs, Giancarlo Stanton became a prime target for the New York Yankees to add to their potent lineup. They made that a reality when they traded for the star outfielder during the 2017-18 offseason. In doing so, they took hold of the remaining 10 years of his massive 13-year contract that Stanton signed with the Marlins back in 2015. That meant he would be the property of the Yankees all the way until his aged-37 season. 

However, Stanton hasn’t been living up to the value of his contract. Prior to joining the Yankees, he was a four-time All-Star, two-time Silver Slugger, along with capturing NL MVP honours in 2017 while finishing runner-up on a separate occasion. But in the following seven seasons with the Yankees, Stanton had only one All-Star season with no World Series appearances to show for as well.

Aside from putting solid numbers for two seasons in 2018 and 2021, his tenure with the Yankees had been plagued by injuries. On top of that, Stanton has even began to show signs of regression in the past three years. His batting average has fallen below his lifetime .257 mark as he hasn’t hit above .233 since 2021. In addition, Stanton has registered less than 50 runs scored, less than 30 home runs and less than 75 RBI in each of his past two seasons. Those were still decent numbers, but considerably off from what he had been putting up during his prime.

In fact, the Yankees actually explored opportunities to potentially move Stanton in recent years. However, with his full no-trade clause, it became impossible for any options to come to fruition. With still another three years left on his contract that seems practically untradeable, the Yankees are likely stuck with him for the foreseeable future.

1. Trevor Story, Boston Red Sox - 6 years, $140 million, $23,333,333 AAV (2027 with club option for 2028)

After just missing out on the World Series when they lost to the Houston Astros in the 2021 ALCS, the Red Sox added Trevor Story via free agency during the 2021-22 offseason to help bolster their offensive lineup.

Story had previously proven to be a strong offensive contributor during his time with the Colorado Rockies, as he had maintained a solid .272 average with 75+ runs scored, 25+ home runs, and 75+ RBI yearly throughout his six-year tenure with the club. However, some were wary about the fact whether his numbers would transfer over to his new team. That was because most believed that they were inflated due to playing at Coors Field, which is known to be a hitter’s ballpark.

However, the Red Sox never really had the opportunity to test that hypothesis as Story has been beset by a slew of injuries since joining the club. That included major injuries to his right elbow in 2023 and to his left shoulder in 2024. As a result, over the past three years, he has appeared in only 163 games in total, which in effect was almost equivalent to just one full season. Cumulatively, Story has posted just a .232 batting average with just a .693 OPS, along with 73 runs scored, 38 doubles, 21 home runs and 90 RBI between 2022-2024 with the Red Sox.

Boston originally looked to Story to help make up for some of the lost offence after the departure of star shortstop Xander Bogaerts following the 2022 season. However, with Story constantly finding himself looking in from the sidelines instead, his impact on the club has remained minimal and ultimately disappointing to say the least.

At least Story showed some glimpse of hope for the Red Sox when he finally made it back into the lineup in September and batted .270 with 7 runs scored, 2 home runs and 6 RBI over 18 games. Hopefully, it will be the turning point for him in what has been a tumultuous tenure with Boston so far. However, if he continues to be befell by injuries going forward, his contract could be heading towards Stephen Strasburg territory..