Where does Anthony Santander's contract rank among the worst in Blue Jays history?

Last off-season the Toronto Blue Jays make numerous efforts to get the team back on track for 2025 after a disappointing 2024 campaign. Among those moves was the addition of slugger Anthony Santander on a five-year deal worth $92.5 million.

The deal currently ranks as the fourth biggest signing in franchise history, though many have been disappointed so far by the lack of production from Santander. In the first year of the deal, there was much to be desired as the slugger produced a mere -0.9 fWAR, an active detriment to the team when he played, and was limited to just 54 games after missing time due to a shoulder injury. Matters were made worse recently as the team announced that Santander would be expected to miss a large portion of the season after undergoing left labral surgery, instantly crushing hope that a 2026 bounce back season was in store.

While the heavy deferrals make the contract worth about $68.6 million in present day value, many would expect a player being signed at that value to not be a negative asset on the field. While there is still time left for Santander to turn things around and change the narrative, the deal is off to a rough start and is looking like one of the worst deals in franchise history.

Where does Anthony Santander's contract rank among the worst in Blue Jays history?

Here is how the deal stacks up compared to the other biggest free agent deals in Blue Jays history.

*$ per fWAR does not include the full value of active contracts
*Martin did not play full contract with the Blue Jays, Dodgers paid $3.6 million in 2019

Compared to the rest of the Blue Jays biggest signings, the value pales in comparison. The Blue Jays have paid Springer a little over $8.4 million per win provided over the duration of the contract, which includes his subpar production over the 2023 and 2024 seasons. To compare mathematically, Santander’s negative value should be paid back to the Blue Jays instead of the inverse.

Now this might be an unfair comparison because these deals have all worked out well for the Blue Jays. But even compared to some other deals the Blue Jays made in free agency, the Santander contract will stand out for the wrong reasons.

It is important to note that for much of the Blue Jays’ history, the team did not take very many big swings in free agency. The signing of Dylan Cease this offseason was just the third free agent contract worth $100 million or more the Blue Jays have offered. Many other poor value deals the Blue Jays have signed were either worth less money to begin with, were one year deals (José Bautista after 2016) or had little expectations come with them (Jaime García after 2017).

Signings such as Kendrys Morales and Tanner Roark come to mind as deals that had some considerable money attached and came nowhere close to living up to their value. These are the kinds of deals that should be considered when making these distinctions.

*Morales did not play full contract with the Blue Jays, paid $31 million of contract

These are some of the worst value signings in Blue Jays history that carry considerable amounts of money. No one year deals, no prove-it deals and no deals without expectation.
All of these deals carry context behind them. For example B.J. Ryan’s contract is mentioned among the worst because he blew out his elbow, but at the end of the day value is value.

Out of these five deals, three of them should owe the Blue Jays money, and one of them was so poor value that the Blue Jays would have to pay over triple the value of the actual contract for one win.

It is tough to judge a multi-year deal, especially one as long as Santander’s so early on, especially since it could end up being a six year deal, and it is also hard to compare it to contracts that have been played out in their entirety. 

With that said, Santander’s deal with the Blue Jays is off to a rough start. In the first season he was actively a negative for the team when on the field, and is going to miss a significant amount of time in his second season. He will also enter the third season at age 32 which is rather concerning.

Of course, Santander still has plenty of time to turn it around and remove himself from these conversations, and there is still reason to believe that he will do so. On the other hand, it is so far undeniable that this is on pace to be potentially the single worst value signing that the Blue Jays have made in their franchise's history.