Ranking the Blue Jays’ Most Painful Contracts Right Now
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One of the most encouraging trends around the Toronto Blue Jays organization in recent years has been a willingness from the Rogers ownership group to spend. Since 2021, the club has landed the likes of Dylan Cease, George Springer and Kevin Gausman in free agency on nine-figure deals.
By and large, that spending has worked out pretty well. The Blue Jays probably don't reach the World Series in 2025 without Springer and Gausman, while Cease was one of the lone highlights from Toronto's 2026 season after putting forth a Cy Young-caliber campaign.
That being said, costly mistakes have been made too. With the MLB GM meetings set to get underway and with president Mark Shapiro and GM Ross Atkins looking to address a roster that under-achieved in 2026, it's a good time to assess the less desirable contracts that remain on the organization's books.
3. Andres Gimenez - 3 Years, $70.71 Million Left (Plus Team Option)
It is possible to remain a good, productive player while still holding an onerous contract. Such is the case with Andres Gimenez, whose late 2024 trade to the Blue Jays was made possible by the Cleveland Guardians wanting to rid themselves of the seven-year, $106 million deal they handed the shortstop before the 2023 season.
Gimenez has helped solidify Toronto's infield defense over the past two seasons, but at a very steep cost. As his annual salary continues to inflate, the club is largely paying for his success with another team.
It was with the Guardians that the 28-year-old earned his three Gold Glove awards and his All-Star nod. Now, the Blue Jays are left to pay over $23 million annually to a player who has produced a .628 OPS over two years.
2. Jose Berrios - 2 Years, $48 Million Left
Jose Berrios got paid $18.7 million last season without making a single appearance on the mound for Toronto. And things don't look much more encouraging as he heads into 2027.
Berrios sat out the early portions of the 2026 campaign while dealing with elbow inflammation and discomfort and appeared to be on track for a return before subsequent tests revealed the need to undergo Tommy John surgery.
His recovery remains on-going, with a return to the mound anticipated around June. Even then, it will be hard to know what to expect from the 32-year-old after what will be more than 18 months spent sidelined.
It came as no surprise that Berrios opted into the final two years of a contract that still owes him roughly $48 million. More uncertain, however, is what the team can expect from the Puerto Rico native who also wasn't particularly effective (9-5, 4.17 ERA) in his last healthy campaign.
1. Anthony Santander - 3 Years, $52 Million Left (Plus Team Option)
When all is said and done, the five-year, $92.5 million contract that Anthony Santander signed prior to the 2025 season may well go down as the organization's worst of all-time. And it seems to keep getting worse.
Upon debuting with the Blue Jays in 2025, Santander experienced a sharp offensive drop-off, struggling to get on base (.175/.271/.294) or hit for power (six home runs, 18 RBI in 54 games. Then came shoulder injuries and back tightness that shelved him for most of the year.
Ahead of 2026, he underwent left labral surgery and would go on to miss the entire season. Most recently, Toronto's PR team had to address controversial social media activity from the 32-year-old in the aftermath of the U.S. mid-term elections.
There's still time for a healthy Santander to turn things around in Toronto, but he's got a lot of work to do if he doesn't want to go down as one of the worst free agent signings in team history.
Dishonorable Mention: Vladimir Guerrero Jr.
It would have been unfair to include Vladimir Guerrero Jr. among the Blue Jays' 'worst contract' list, but the pink elephant in the room should probably still at least be addressed.
Toronto is in all kinds of trouble moving forward if Guerrero Jr. can't find his way out of his 2026 funk, not the least of which because they are just one year into the 14-year, $500 million mega-contract that easily stands as the biggest in franchise history. That contract was intended for a game-changing superstar, not a rally-killer with a single digit home run total and a .260/.332/.356 slash line.
If Guerrero Jr. continues at this pace, he might wind up holding one of the worst contracts in all of MLB.
Shapiro and Atkins have, by and large, done well with their home run swings on contracts. And who knows, if everyone remains healthy and productive, maybe these contracts will age a little better than anticipated. If not, the club's brain trust has some work to do to divest themselves of contracts that Rogers surely won't want to be on the hook for.
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Ben Fisher is a long-time sportswriter and baseball lover, dating back to 2008, when he was a member of the media relations team for the Toronto Blue Jays. He has covered a wide range of sports for a seemingly endless array of publications, including The Canadian Press, Fansided and The Hockey Writers. When he isn't writing about sports, he can be found coaching his equally baseball-obsessed sons' Little League teams.