The Blue Jays have spent aggressively in recent years, and plenty of those bets have paid off. George Springer and Kevin Gausman helped push Toronto to the World Series in 2025, while Dylan Cease delivered a Cy Young-caliber season and stood out as one of the few bright spots in the club’s 2026 campaign.
But not every expensive swing has landed. With the MLB GM meetings approaching and president Mark Shapiro and GM Ross Atkins facing a roster that under-achieved in 2026, it’s a fitting time to look at the contracts that have become the heaviest burdens on Toronto’s books.
Andres Gimenez is the kind of player who can still help a team while carrying a deal that feels far too rich. Toronto acquired him in late 2024 after the Cleveland Guardians wanted to move the seven-year, $106 million contract they gave him before the 2023 season. Gimenez has stabilized the Blue Jays’ infield defense over the last two years, but the price tag is steep: more than $23 million annually for a player who has posted a .628 OPS over that span.
The offense has not matched the salary, and the Blue Jays are essentially paying for what Gimenez accomplished elsewhere. With Cleveland, the 28-year-old earned three Gold Gloves and made an All-Star team. In Toronto, the production has not come close to justifying the commitment.
Jose Berrios is another expensive headache, and his situation is even murkier because he didn’t throw a pitch for Toronto last season. He earned $18.7 million in 2026 while sidelined, first by elbow inflammation and discomfort and then by Tommy John surgery after further testing changed the outlook on his return.
His rehab is still ongoing, with a return to the mound expected around June. Even then, there’s plenty of uncertainty around what the 32-year-old will look like after more than 18 months away from game action. Berrios opted into the final two years of a deal that still owes him about $48 million, and his last healthy season wasn’t exactly reassuring either, as he went 9-5 with a 4.17 ERA.
Anthony Santander may be the contract that haunts Toronto the most. The five-year, $92.5 million deal he signed before the 2025 season could end up as the worst in franchise history, and the early returns have been rough. In 2025, Santander’s offense cratered as he hit .175/.271/.294 with six home runs and 18 RBI in 54 games before shoulder injuries and back tightness shut him down for most of the year.
The problems only piled up from there. He had left labral surgery before 2026 and missed the entire season.
More recently, Toronto’s PR team had to respond to controversial social media activity from the 32-year-old after the U.S. mid-term elections. There is still time for Santander to change the story in Toronto, but he has a long way to go if he wants to avoid being remembered as one of the club’s worst free-agent signings.
Vladimir Guerrero Jr. doesn’t belong on a “worst contracts” list just yet, but his situation is impossible to ignore. Toronto is only one year into the 14-year, $500 million deal that is already the biggest in franchise history, and it was supposed to buy a superstar in his prime. Instead, Guerrero Jr. has stumbled through a 2026 slump, hitting .260/.332/.356 with a single-digit home run total.
If that level of production sticks, the Blue Jays could be staring at one of the most difficult contracts in the sport. For now, Shapiro and Atkins can point to a track record that has mostly worked on the big swings. But if these deals don’t turn around, Toronto’s front office will have some serious cleanup to do.
In Other News...
Blue Jays Defense Was Elite But Their Biggest Offseason Problem Is Clear
The Blue Jays season ended with a strange contrast that says plenty about where the roster stands heading into the winter. Toronto was honored as the American Leagues best defensive team, a fitting reward for a club that played clean baseball and turned that into a Gold Glove team award. But the same group that shined in the field never really found its footing at the plate, and the lack of any Louisville Silver Slugger finalists underscored how far the offense lagged behind the glove work.
For a team trying to climb back into the top tier of the American League, the imbalance is hard to ignore. Torontos offensive issues were broad enough that the front office will have to treat lineup help as a priority, with names like Seiya Suzuki already in the conversation as possible fits. The challenge is not just adding one bat, but finding enough impact to make the Blue Jays look as complete with the bats as they already do in the field. [Read more 🡒]
Blue Jays Prospects Could Shape Torontos Next Big Winter Move
The Blue Jays have never been shy about using their prospect depth to chase help at the big-league level, and that history is part of what makes this winter worth watching. Toronto has already shown a willingness to move top-ranked young talent in the past, and this latest group of prospects gives the front office another batch of names to weigh as it looks for ways to strengthen the roster.
Among the players in that mix are Sean Keys and Nolan Perry, two prospects whose recent progress has put them squarely on the radar for different reasons. Some of the group could still carve out roles in Toronto, while others may be viewed more as trade pieces if the Jays decide the best path to improvement is to deal from their system again. [Read more 🡒]
Blue Jays Face One Big Sonny Gray Question This Winter
Sonny Gray has spent 14 big league seasons building a reputation as one of the more dependable starters in the game, and that kind of reliability is exactly the sort of trait the Blue Jays will be weighing as they shape their rotation this winter. Even with his recent work showing some age-related change, Gray has still been able to keep runs off the board and give a club a steady presence every fifth day, helped along by strong defense behind him.
For Toronto, the appeal is obvious because the rotation picture is not settled and the front office could use a proven arm to stabilize it. Gray fits the profile of a pitcher who can still matter without overpowering hitters the way he once did, which makes him a logical name to monitor as the Jays sort through their options and decide how aggressive to be in adding help. [Read more 🡒]