Rarely are contract negotiations straightforward, but the negotiations between the Toronto Blue Jays and Vladimir Guerrero Jr. would never be cut and dry. A talented player with an uneven history in the big leagues was bound to have a chasm between his value and the Blue Jays’ value.

The criticism of the Blue Jays’ front office for failing to come to an agreement by Vladdy’s self-imposed contract deadline is largely justified. Guerrero isn’t as good as gone, but it’s one more juncture where the Blue Jays failed to anoint their franchise player.

Even looking at Guerrero’s contract comparables are full of red herrings because there isn’t a proportional template to build a contract extension upon. A 25-year-old first baseman with two top-10 MVP finishes in his first six seasons, two “good” seasons, and two “okay seasons”. How do you go about finding a comp for that?

The Blue Jays had to build some valuation model to determine what they should offer Guerrero for a contract extension, but there are no guides for how to approach this. This is partially why the Blue Jays and Vladdy were not “close” to a deal.

Without knowing the numbers, it’s hard to say who’s at fault here, but suffice to say if they were both in the same ballpark, there would be some negotiating toward a middle ground. But if that chasm was, for example, $100 million or more, it’s very difficult to see a team closing that gap.

Although we don’t know how often over the last six years the Blue Jays and Guerrero’s camp talked about contract extensions, there were many junctures where this team couldn’t justify locking up the player long-term.

Were the Blue Jays knocking on Vladdy’s door after following up his monster 2021 season with a 3.3 win season in 2022? Or did they pick up extension talks after Vladdy came back in 2023 after taking a step back further with a 1.3 win season?

There were only two times when it made sense for the Blue Jays to consider making a big bet on Guerrero; at the conclusion of the 2021 season and this past season. There have been so many question marks about Guerrero in between those two tent pole seasons that it’s difficult to project which iteration of Vladdy the Blue Jays would be getting.

This is my personal conspiracy theory, but perhaps one reason the Blue Jays were aggressive in their free agent pursuits of players like Shohei Ohtani, Juan Soto, and others is because the team had a strong indication guys like Guerrero and Bo Bichette would test free agency all along.

Unlike other players in Guerrero’s position, he grew up comfortably financially thanks to his father’s earnings as an MLB player. Young Vlad has seen how this process works, and there is no incentive for him to take a “hometown discount” to stay in Toronto.

Second-generation MLB players are even more likely to bet on themselves and that’s how this is looking to play out with both Guerrero and Bichette at the end of this season. They know the allure of free agency because their fathers experienced it firsthand.

So you have this volatile mix of a front office looking for value and a player who wants nothing but. And remember, teams don’t sign young players to mega contracts out of the goodness of their hearts. They do it because that player could become even pricier in the future if their career continues on the current trajectory.

The problem with Vlad forecasting his career trajectory. Yes, he had a solid 2024 campaign, but he didn’t kick his season into high gear until June, two-plus months into the season. The peaks are high with Guerrero, but those valleys can be troubling, too.

Making a play for a free agent means you’re investing in a player in their late 20s or early 30s, but that also comes with a lot more uncertainty. Before landing with the Mets, Soto already has four 5-plus WAR seasons under his belt at 26 years old. Guerrero so far only has two.

Instead of being aggressive, this front office stayed “disciplined” as Ross Atkins and Mark Shapiro noted in contract extension talks with Guerrero. Fans can say “pay the man his money” all they want, but the front office doesn’t get a blank cheque without making a strong business case to support that level of spending on one player.

From Vladdy’s standpoint, he shouldn’t be surprised things got to this point, either. After ten years within this organization and nine years with this regime, Guerrero and his representatives know how Atkins and Shapiro operate.

This front office doesn’t make Steve Cohen-esque moves in free agency. In the past nine years, they only signed two Blue Jays players to contract extensions (Jose Berrios and Randal Grichuk), and they rarely go above market value to land a player.

Granted, the Blue Jays haven’t seen a player like Guerrero come through their system in the last nine years, but a lack of betting big on internal players is telling for how this front office conducts business.

So with Guerrero knowing the guys he’s negotiating with, and with the front office not sold on who the player is, it shouldn’t be a surprise they haven’t come to an agreement. That’s not to say it still can’t happen, but the longer this drags out, the more expensive Guerrero gets, and the more likely he’s playing elsewhere in 2026 and beyond.

No matter how you look at it, this is a gamble for all sides. A deal of this magnitude involves the team taking on more risk than the player, but it involves the player giving up something on their end as well.

Behind the scenes, there’s a formula the Blue Jays have developed for determining Guerrero’s worth. And if their number is different from the player’s number, no amount of emotional value or franchise clout will convince the Blue Jays to close that gap. Even for a player as talented and with as much potential as Guerrero.

Many people can see that he’s a generational player worth a sizeable contract, but Atkins and Shapiro do not. That’s their perspective, but watching a generational player swap jerseys to make your life a living hell isn’t a scenario that should have played out here.

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