Which recent Blue Jays trade still hurts the most?

Playoff baseball is exhilarating for all of those involved. When your job title is competing at the highest level, there is nothing like participating in the postseason. The frustrating part has been watching former Blue Jays have fun while Toronto is playing golf. That impact was felt last season with Gabriel Moreno in the desert and now this season with Teoscar Hernandez in Tinseltown. Speaking of, which of those two recent maneuvers do fans regret the most?

Hernandez and Moreno were both sent packing in the same winter under different trades. Teo spent six seasons north of the border in which he largely established himself as a durable middle-of-the-order power bat. In 609 games with Toronto, he posted a 122 OPS+, 129 home runs, 369 RBI and an OPS over .800 in four of those seasons.

So, why exactly was he sent packing? Well, it's a part of that potentially misguided gambit to shuffle offense for defense undertaken after that crushing postseason loss to Seattle. Toronto wanted to remake the makeup of their outfield in transformative ways. They brought in intriguing hurler Adam Macko...except he has yet to pitch in a Jays uniform. They imported Erik Swanson in that deal...except he just turned in an extremely disappointing second season after a solid first one in 2023.

The Moreno trade is receiving less acclaim nowadays, but that may be a function of Arizona not participating in these playoffs. Rewind to last autumn and we are singing a different tune. Think back to Christmas Eve 2022 and you will remember Gabriel Moreno and Lourdes Gurriel Jr going to Arizona in exchange for Daulton Varsho. Moreno slashed .284 in 111 games for Arizona in his first season. 2024 was a bit of a step-back mostly due to injuries, hitting .266 in 97 games.

The name of the game in baseball nowadays is cost certainty and locking up homegrown talent. Look at Alex Anthopoulos' Atlanta Braves and the extensions they have handed out to almost every member of their young core. Sure, they need those players to sign contracts early and potentially forego the big payday of free agency. The teams, however, see it as a brilliant opportunity to lock up a building block for years and there is nothing better from a roster perspective than certainty. Moreno could have offered that possibility for the Blue Jays. Getting a building block behind the plate is difficult and costly. The Braves had to surrender William Contreras and a top prospect to acquire Sean Murphy, who since signed a team extension to stay in Atlanta.

Moreno and Hernandez have both shown the ability to get big hits on the bright October stage. This part of the story is a wash. Think of the huge Moreno single in Game 4 of the 2023 NLCS that evened up the series. How about the final blow he delivered to Philadelphia fans in Game 7 against reliever Jeff Hoffman? Hernandez has belted two home runs this postseason, including a grand slam that nearly led to a Dodger upset in Game 2 of the NLCS. His insurance home run against Yu Darvish in a winner-take-all Game 5 certainly qualifies.

The tipping point for why the Moreno trade is worse is in what it means for the future, a period of time that Jays fans can only hope is more prosperous than the recent past. The Jays badly miscalculated in surrendering a potentially enormous contributor of their future. Moreno is basically the same age as Vladimir Guerrero Jr. and could have starred alongside his fellow run producer in the Toronto lineup. Hernandez's impact was probably felt most acutely in the personality he exuded in the clubhouse.

Teo would have been a big offensive contributor but always seemed like a guy who wanted to play for a winning team, something that Toronto may not have been able to provide. The Jays clearly wanted to extract a maximum return from him before he hit free agency. Does it speak to their unwillingness to potentially meet his asking price? Hernandez's current exploits are definitely setting himself up for a massive winter payday.

Similar to most baseball trades, it's a little early to precisely "grade" the trades. The results will begin to crystallize with time. In the present moment, however, they perfectly capture the conundrum the Blue Jays find themselves in.