Blue Jays fans have had a disappointing couple of days with some of the best remaining free agents coming off the board. First, it was former Blue Jay Teoscar Hernandez re-signing with the Dodgers on a new 3-year contract after reportedly flirting with a return to Toronto at times over the last few weeks. Then, late on Friday evening, the bombshell came that Corbin Burnes had signed a 6-year pact with the Arizona Diamondbacks in a deal that almost no one could have predicted.

Those moves are especially disappointing because the Blue Jays were reportedly involved in the bidding for both players, and according to USA Today’s Bob Nightengale, it sounds like they even made a more aggressive bid for Burnes before he signed with the Diamondbacks. Some would argue that you can’t fault Ross Atkins and the Blue Jays front office when they’re making competitive bids for free agents that just aren’t being accepted, but of course, it’s never that simple and many others would argue the opposite.

To compound the early-weekend disappointment even more, TSN’s Scott Mitchell reported that Teoscar Hernández’s camp was seeking a contract of roughly five years and $120 million as an extension before he was traded to the Seattle Mariners in 2022.

At the time Hernández was a year away from free agency, and the deal arguably made sense as the Blue Jays were facing the eventual need to extend other, bigger priorities, like Vladimir Guerrero Jr. and Bo Bichette (still waiting on that…). They also received a late-inning reliever in Erik Swanson, who was very effective in 2023 and came with three years of contract control, as well as Adam Macko, a promising young left-handed pitching prospect that impressed in 2024 around time lost due to injury. As angry as some fans are about that trade, I still believe it was a reasonable return for one year of contract control for Hernández, and to be fair, he struggled and disappointed in 2023 with the Mariners, so we would likely be seeing this whole thing differently a year ago.

However, with two years in the rearview, and with the benefit of this nugget of information that Mitchell dropped on Friday, did the Blue Jays royally screw up by trading Hernández rather than extending him? The easy answer is yes, now that we’ve seen how well he performed with the Dodgers last year, but I figured it’s worth taking a closer look at a few of the variables that would go along with that.

The biggest thing to consider would be the opportunity cost if they had given Hernández a 5-year extension back in late 2022. While it’s easy to say that the Blue Jays have all the financial muscle they need to do basically whatever they want, this organization has always operated with some level of restraint, even if they’re currently among the top spenders in the game over the last few years. With that in mind, I think it’s fair to look at how the Blue Jays spent their money around the time that they traded Hernández to the Mariners. Keep in mind, this was also the same offseason that they traded fellow corner outfielder Lourdes Gurriel Jr. along with Gabriel Moreno to the Diamondbacks in exchange for Daulton Varsho.

Re-signing Hernández would have also surely have meant that the Blue Jays would have never have signed Kevin Kiermaier. As much of a fan favourite as he became in his two seasons in Toronto, that part is of little consequence. More importantly, I don’t know if the Jays would have had the available payroll space to sign Chris Bassitt, who has been an important part of their rotation over the last two seasons, especially as they’ve dealt with significant injuries to key homegrown talents like Alek Manoah and Ricky Tiedemann. I realize that having Bassitt around hasn’t taken this team to the World Series or anything, but it’s hard to argue against his value to the pitching staff over the last two years, and I don’t know that he ends up in Toronto if the Jays had already spent money to retain Hernández.

It wouldn’t necessarily have meant that they couldn’t have signed Bassitt, but the point here is that the money would have come from some other part of the roster. That’s the domino effect that comes with handing out contracts of 20 million of more per year, and back then I understood why the Blue Jays were hesitant to do it. If they had, Hernández would be two years into that deal, and with three remaining, it would basically match the current situation he’s in after inking a 3-year deal with the Dodgers this week. For what it’s worth, the 32 year old made $14 million with the Mariners in 2023, and $24.5 million last season in Los Angeles according to Spotrac.com. That’s also something worth considering, as the Blue Jays likely would have backloaded his deal a bit back in 2022 as well, and that could have lead to a higher AAV than the $22 million per season that he’ll earn with the Dodgers on his new contract.

Don’t get me wrong, it’s very easy to argue in hindsight that the Blue Jays should have extended Hernández and worked around the money they would have spent by doing so. Teoscar continues to be an impact middle of the lineup hitter, and there’s no disputing that the Blue Jays are in need of just that. There are also other variables like his friendship with Vladimir Guerrero Jr., and all the “what ifs” that come with reflecting on the missed opportunities to have already extended the face of the franchise, but that’s also impossible to predict how impactful it might have been.

To me, missing out on Hernández now is arguably as bad or even worse than it was letting him go at the time in 2022. It’s possible that he wanted to return to the Dodgers all along anyway, but losing yet another free agent option really stings this time, especially as the market continues to dwindle and the Blue Jays are still looking for offensive upgrades. To make matters worse, Vladimir Guerrero Jr’s contract status really feels like it’s come to the forefront at this point, and bringing back Hernández felt like it could be a precursor to extension for Guerrero Jr. as well. Now we’re left still hoping the Blue Jays can acquire an impact bat or two, and left waiting to see if they can retain their homegrown slugger.

In hindsight, I’m sure the Blue Jays would love a mulligan on negotiating a deal with Hernández back in 2022, and unfortunately they couldn’t bring him back this time around either. Here’s hoping Atkins and co. can turn the opportunity cost of missing out on Hernández, and also Burnes, into something significant.