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.