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The Toronto Blue Jays have now embarked upon the tenth—tenth!—offseason of the Mark Shapiro and Ross Atkins era, and you’re probably well aware right now that it’s a big one.
There’s no sugarcoating it: the Jays are poised to fall off a cliff if they don’t get Vladimir Guerrero Jr. signed to a contract extension and upgrade the roster around him for 2026 and beyond—which is to say nothing of what needs to be done to make the team competitive in 2025.
Now, some may say that the team already reached that cliff in 2024 and that we might as well let them continue to fall, but obviously that’s as silly and cowardly as it is completely misaligned with the current goals of ownership and the front office.
They’re swinging for it, they simply need a home run.
But threading that needle and avoiding a grim future in which, a year from now, the only players the team has dollars committed to are George Springer, Kevin Gausman, José Berríos, and Yariel Rodríguez—and even Daulton Varsho and Alejandro Kirk will be headed into their final seasons before free agency!—isn’t going to be easy. Even though they upgraded their prospect pipeline at the trade deadline, and even with Bowden Francis potentially turning into something real, plus Alek Manoah and Ricky Tiedemann potentially being factors again for ‘26, it just doesn’t feel like the bones of a championship-calibre team will be here without a lot of help.
Does this group have it in them to get there? Well, not all of that is necessarily in their control. The market can’t offer every solution to every problem, and even when it does, it’s awfully competitive. We’ve already seen Yusei Kikuchi, as he heads into his age-34 season, snag a contract with the Angels that almost doubles what he made when signing with the Jays three winters ago. And the Dodgers are out there adding Blake Snell1 to an organization that appears will be limited this winter less by the number of dollars it can throw around and more by the number of starts or plate appearances it can offer a player. It’s tough sledding out there.
But before anyone shouts that obviously this Blue Jays front office can’t get to where they need to go from here, or that maybe someone could but these clowns won’t, I think it would be instructive to actually look back at their previous nine winters of work, and to think about about what they needed to accomplish, what they tried to accomplish, and what they actually managed to accomplish.
And I think the best—or at least most entertaining—way we can do that is by ranking them. So, without further adieu, uh… let’s do that…
9. 2018-19
Major moves: Signed Freddy Galvis ($5M), Matt Shoemaker ($3.5M), Clay Buchholz ($3M), David Phelps ($2.5M), Daniel Hudson ($1.5M); Traded Aledmys Díaz for Trent Thornton.
Minor moves of note: Signed Eric Sogard (MiLB deal); Claimed Elvis Luciano (Rule 5); Traded Russell Martin for Ronny Brito and Andrew Sopko.
If I was some kind of a galaxy-brained clown I might say here that this collection of warm bodies represents an offseason strategy executed to perfection. That this Jays regime, after waiting patiently for years through success—woof!—and expectations—gross!—could finally do the thing Mark Shapiro had been aching for since he first signed on to be Paul Beeston’s replacement in mid-2015 and slam that “We’re gonna be dogshit!” button. But this is truly grim, even judged by the lowest of possible standards.
If you’re going to flip the switch, commit to being bad, and take a long look at as many kids as possible, you at least want to fill in around them with guys who might have a bit of value at the trade deadline. Phelps turned into Thomas Hatch, which looked for a minute like it might have been a good deal. But otherwise?
Galvis was placed on waivers in August and ended up in Cincinnati. The always-injured Shoemaker was a revelation for a month, then got hurt. The Buchholz deal sucked not only because he was awful—he posted a 6.56 ERA over just 12 starts—but because we were made to cheer for Clay fucking Buchholz. Sogard was a great story and racked up 2.5 WAR with a 123 wRC+ over just 73 games and then was promptly spun into Curtis Taylor and Edisson Gonzales. Dan Hudson saved four games in the playoffs, recorded the final out of the World Series, and all they got for him was Kyle Johnston!
Hey, but when you can flex your smartest-guy-in-the-room credentials by taking a kid in the Rule 5 draft who had no business being in the big leagues, and wasting a roster space on him until the second you can fake an injury and put him on the 60-day IL without having to send him back to his previous org., for absolutely zero payoff to you or anyone else, you gotta do it.
8. 2017-18
Major moves: Signed Jaime García ($10M), Curtis Granderson ($5M); Traded Dominic Leone and Conner Greene for Randal Grichuk, traded Edward Olivares and Jared Carkuff for Yangervis Solarte, traded J.B. Woodman for Aledmys Díaz.
Minor moves of note: Signed Seunghwan Oh ($2M), John Axford (MiLB deal); Traded cash for Sam Gaviglio.
Here we have the moves of a team that knows that a transition is coming, doesn’t especially want to be good, but sold a lot of 2017 season tickets in late 2016 by tying them to early access for playoff seats, and for the most cynical reasons possible at least wants to gesture toward relevance in order to keep the cash flowing.
Like a certain failed offseason that would come much later on in Shapiro and Atkins’ tenure, this one was keyed around internal improvements. They didn’t want to bog down their long-term project by committing a ton of cash going forward, and they didn’t especially need splashy, big-ticket moves to sell hope. Hope was already on the roster. All they really needed was better health from Josh Donaldson, Troy Tulowitzki, Devon Travis, Marco Estrada, and Aaron Sanchez, and for Marcus Stroman, J.A. Happ, and Justin Smoak to be as great as they were in 2017.
Literally none of that happened. And while the front office can't be entirely faulted for it, a lot of it was predictable. That’s why I rank this offseason so low. There are transactions that worked out quite well in a vacuum—the Díaz and Grichuk ones, in particular (as long as we aren’t counting the eventual extension for Grichuk as part of it, which looked questionable the day it was signed and only ever got worse)—but it never felt as though this was a year they cared about, even if plenty of talent was still around.
I mean, Happ and Stroman were their only starters coming off of good 2017 seasons—Estrada had begun falling apart with a 4.98 ERA, Sanchez had pitched just 36 innings, Francisco Liriano (18 starts, 5.88 ERA) was gone, Joe Biagini’s rotation experiment had failed (5.34 ERA in 18 starts), and none of the other guys they had used were anything (Brett Anderson, Mike Bolsinger, César Valdez, Chris Rowley, Mat Latos, Nick Tepesch, Casey Lawrence, Tom Koehler)—and yet they only go out and sign Jaime García???
7. 2023-24
Major moves: Signed Yariel Rodríguez (5/$32M), Isiah Kiner-Falefa (2/$15M), Justin Turner ($13M), Kevin Kiermaier ($10.5M); Exercised club option on Chad Green (2/$21M).
Minor moves of note: Signed Joey Votto (MiLB deal), signed Daniel Vogelbach (MiLB deal)
I trust we’re all a bit more familiar with particulars of this offseason than ones from more than a half decade ago, and… yeah. It’s ugly. And if you wanted to flip it in the rankings with the one we just discussed, I wouldn’t have an issue with that. I just happen to like this one a touch better, mostly because at least they were trying.
Damning with the faintest of praise? Oh, absolutely. But they did want to win. Clearly they wanted Ohtani so badly they could taste it, even if that pursuit was destined to fail. They may have liked Kiermaier a little too much, and were a little too eager to buy in on his offensive performance in 2023, but nobody saw his wRC+ dropping by 50 points (to a level 25 points below his previous career low). I understand why they expected better and felt they were unlucky in their pivot toward pitching and defence the previous winter, and why they were reticent to immediately run away from it. I think Justin Turner—who ended up with a better wRC+ (117) than the year prior (115), though just under half as many home runs—could have been a fine signing if they’d found more firepower elsewhere (or got any of it from Bichette, Springer, Kirk, or Varsho). IKF always felt redundant, but I can’t deny that his performance—and the return he landed them in trade—made them look good. And Yariel seems like a nice addition who can perform in a number of roles at a very comfortable price.
It just didn’t once feel like they did enough, and ultimately that feeling was exactly correct. Never give the wailing “Shatkins” chuds that kind of validation, man!
6. 2016-17
Major moves: Signed Kendrys Morales (3/$33), Lourdes Gurriel Jr. (7/$22M), Steve Pearce (2/$12.5M); Re-signed José Bautista ($18.5M).
Minor moves of note: Signed Joe Smith ($3M); Claimed Dominic Leone (waivers).
This ranking isn’t entirely about the Morales deal—or, more aptly, the failure to reach a deal with Edwin Encarnación—but the Morales deal is a whole hell of a lot of it. Given what Encarnación had meant for the franchise, plus the lower-than-expected deal he eventually received from Cleveland, and the fact that Kendrys fell on his face in his first year with the Jays, it felt absolutely disastrous and still does.
And yet, the idea that Morales could approximate what Edwin could do on the field well enough for a much cheaper price wasn’t necessarily an awful one. He was decent enough in year two to wipe some of the egg from Ross Atkins’ face. The second year of the Steve Pearce deal made that one look a whole lot better, as well. Unfortunately, the first years for both players were incredibly underwhelming, with Pearce posting a 100 wRC+ and Morales a 98.
Add in Bautista’s ugly, 81 wRC+ swan song and I think you could say that this winter’s work accelerated the Jays’ descent into their rebuild more than any other’s.
Still, I can’t entirely hate this one. Getting Gurriel was a great move (and perhaps tied to Morales2), letting Edwin go brought back the draft pick used on Nate Pearson, and though Bautista’s year was ultimately very tough to watch, bringing back the club legend for one more ride was the right thing to do. If you’re going to fail, at least fail with fan favourites—an idea the front office would have done well to keep in mind with Edwin.
5. 2015-16
Major moves: Signed J.A. Happ (3/$65M), Marco Estrada (2/$26M); Traded Ben Revere for Drew Storen.
Minor moves of note: Signed Darwin Barney ($1.05M); Claimed Joe Biagini (Rule 5); Traded Liam Hendriks for Jesse Chavez
In a vacuum this one really isn’t so bad. The Happ deal turned out very well, and bringing back Estrada after some qualifying offer drama was beautiful. The team ended up going to the ALCS for a second straight season. And even their two big whiffs—“Two’s Scorin’” was a wreck and Hendriks would go on to great success a few years later—were really only minimally damaging.
But I certainly couldn’t rank this one any higher. This was not just the winter that Alex Anthopoulos was allowed to move on, it was the winter when the new regime had the chance to think big and be ambitious—a moment when any top player in the world would have been thrilled for a chance to join the Blue Jays—and instead chose to unambiguously shrink from it.
There were many reasons for that, some more justifiable than others. Mark Shapiro wasn’t yet the Edward Whisperer. He hadn’t been hired to step on the gas in terms of spending—at least not until the team could modernize and improve upon their “premium” revenue streams. So, even with the massive success in 2015, payroll wasn’t suddenly going to jump into the top five in the league. Plus, the roster was aging and many of the club’s best prospects had just been dealt away. They could be good for as long as the Bautista-Donaldson-Encarnación core would allow, but the path toward “sustainable” success was far from obvious.
Thing is, to find that sort of a path, you need to be open to it, and you need vision. These guys seemed ready for a rebuild from the jump, and rather than being big and bold and befitting of the situation Anthopoulos had left for them—rather than rewrite the business case for spending big after seeing what this market will do for a winner—their moves in this offseason spoke to a desire to wind things down and start afresh like they had always planned. And that’s exactly what ultimately happened.
I might have assessed this one differently had things gone better in 2017 and 2018—which they could and really probably should have—but there was an opportunity here to try to set those seasons up even better and they declined to take it.
4. 2019-20
Major moves: Signed Hyun-Jin Ryu (4/$80M), Tanner Roark (2/$24M), Shun Yamaguchi (2/$6.35M plus a $1.27M transfer fee); Travis Shaw ($4M); Traded Chad Spanberger for Chase Anderson.
Minor moves of note: Signed Rafael Dolis ($1M); Signed Joe Panik (MiLB deal).
If my ranking of the 2016-17 offseason wasn't entirely about the Morales deal, my ranking of this one isn't entirely about the Ryu one. But, as in that case, it's a whole lot of it.
And it would have to be to get a ranking this high. I mean... all those other moves? Woof. Yamaguchi was a disaster, washed “diesel engine” Roark was an expensive and particularly grating disaster. Just absolutely nothing of note to speak of here. Even the Ryu deal looks like a rough one in terms of on-field value.
Of course, it wasn't only about that.
The Ryu signing announced to the world that the Blue Jays were serious, and that they were turning the corner. He wasn't the best, youngest, or most sparkling free agent available, but it was the most significant deal the team had signed since Russell Martin in November 2014. It meant something.
Plus, it was a olive branch to uber-agent Scott Boras, whose fractured relationship with the Blue Jays—and, mostly, Shapiro's predecessor, Paul Beeston—dated back to the mid-80s and tensions over the use of Bill Caudill (the closer usurped by the emergence of Tom Henke who is now mostly remembered for a Boras-paid message flown from a plane over Exhibition Stadium in June 1986, telling manager Jimy Williams to “Give Caudill the ball”).
It also doesn’t hurt that Ryu went out and pitched his ass off, dragging the Jays into the playoffs in the expanded field of the shortened 2020 season, then giving them half of a great season in 2021 as well. The rest of that year, and of his Jays career, wasn’t particularly fun or noteworthy, but Ryu was a likable enough figure that it hardly matters. An incredibly important deal for this era of Blue Jays baseball.
3. 2022-23
Major moves: Chris Bassitt (3/$63), Brandon Belt ($9.3), Kevin Kiermaier ($9M), Chad Green (2/$8.5); Traded Teoscar Hernández for Erik Swanson and Adam Macko, traded Gabriel Moreno and Lourdes Gurriel Jr. for Daulton Varsho.
Minor moves of note: Signed Jay Jackson ($1.5M); Exercised club option on Anthony Bass ($3M)
Look, I know that everyone now hates the pivot the Jays made in this offseason, and that everyone struggled with the Teoscar and Moreno/Gurriel deals in the first place, but this was a really, really good winter for the club.
Bassitt has easily held up his end of the bargain so far. Belt, thanks in part to receiving favourable matchups, posted a team-leading 138 wRC+ over 404 plate appearances in ‘23. Kiermaier had his best year since 2017, putting up a 104 wRC+ and a 3.9 bWAR. Swanson was an outstanding leverage reliever, and the money saved based on the difference between his salary and Teoscar’s helped the club bring in those other guys. And Varsho, though a disappointment at the plate, has turned into maybe the best defensive outfielder in baseball, and has helped lead the Jays to two straight AL Gold Gloves for team defence.
Obviously this particular offseason will be remembered more for what was lost than what was gained. Teoscar and Lourdes were incredibly fun players to watch, and the change of identity from being a team that has a blast mashing the baseball to one that rather seriously plays very good defence has been deflating to watch and failed to bear fruit. It may be the winter that ultimately defines the legacy of the Shapiro-Atkins era, and not in a good way. But by and large it worked. And if the team hadn’t suffered from an absurdly brutal three-month run of RISP luck in mid-2023, I think that would be better understood.
2. 2020-21
Major moves: Signed George Springer (6/$150M), Marcus Semien ($18M), Robbie Ray ($8M), Kirby Yates ($5.5M); Traded Sean Reid-Foley, Yennsy Díaz, and Josh Winckowski for Steven Matz.
Minor moves of note: Signed Tyler Chatwood ($3M), David Phelps ($1.75M), Joe Panik (MiLB deal); Claimed Anthony Castro (waivers).
The Springer deal may have started aging poorly sooner than anybody would have liked, but even if that had been the only contract the Jays had signed, this winter would have ranked quite high on this list. Add it to the other moves and we find it very nearly at the top—and I think there's a good case to have it even higher.
I mean, getting a top-three MVP season (Marcus Semien) and an AL Cy Young award (Robbie Ray) for just $26 million combined could only be more of a home run if the deals ran longer than just a single year. Getting the best season of Steven Matz’s career for three guys sliding their way off the 40-man was an absolute coup. And then you add in the biggest, most significant contract in franchise history? A contract that told the world, if they didn't believe it when the Ryu deal happened, that the Blue Jays were a burgeoning powerhouse?
Incredible stuff in terms of scope, ambition, filling the team's needs, and actually hitting on the right players at the right time. Tyler Chatwood couldn't even spoil that mood.
1. 2021-22
Major moves: Signed Kevin Gausman (5/$110M), Yusei Kikuchi (3/$36M), Yimi García (2/$11M); Traded Kevin Smith, Gunnar Hoglund, Zach Logue, and Kirby Snead for Matt Chapman, traded Randal Grichuk and cash for Raimel Tapia and Adrian Pinto; Extended José Berríos (7/$131M).
Minor moves of note: Signed David Phelps (MiLB deal), Tyler Heineman (MiLB deal), Dexter Fowler (MiLB deal); Traded Antjhony Castro for Bradley Zimmer; Traded Reese McGuire for Zack Collins.
What do you do as an encore after a winter like the one I’ve ranked number two? Get it just about perfect again.
Like I say, you could make a case for the previous one taking the top spot here, but I like this one just a little bit better. The Jays had to move directly from the heartbreaking end to their 2021 season into a very difficult winter with some massive decisions to make. Marcus Semien and Robbie Ray represented 10 wins combined, according to fWAR. Both were free agents looking for gargantuan deals, and had very quickly become fan favourites.
Could the team really keep both? If so which one? And, if not, how could they make sure not to squander their newfound status as potential World Series contenders?
It was a difficult needle to thread, but as we know they got it right. Or thereabouts.
Semien was offered a seven-year, $175 million deal with the Texas Rangers, and the Jays were unable or unwilling to match. He’s continued to be a great player for them, and I certainly wouldn’t say it was the right decision to walk away. Personally, I like Semien a whole lot. But he was a league average hitter in 2024 and, as he heads into his age-34 season, is still owed $98 million over four years.
In the meantime, the Jays traded little of value (though Gunnar Hoglund still has a chance to change that narrative, I suppose) for two years of Matt Chapman.
Chapman’s Jays years were far from perfect, but he racked up a lot of value in them. Granted, that was mostly with his glove, and FanGraphs has him four wins behind Semien over those two seasons. But he cost a whole lot less while getting off the books much sooner. It may not be sexy, but that flexibility is important—even if they didn’t do a whole hell of a lot with it in 2024.
Meanwhile, the Jays said goodbye to Ray, who went to Seattle for five years, $115 million, and instead added Kevin Gausman for five years, $110. Even if Gausman's 2024 was a little bit worrying, hoo boy, did they ever bet on the right horse there.
Ray lasted just 192 1/3 innings with the Mariners, or one fewer than his 2021 total with the Jays. After a fine enough debut year in Seattle, Ray made just one start in 2023 before being shut down for the season due to Tommy John surgery. In January of this year he was traded to the Giants, and after his return he gave them just 30 2/3 innings over seven starts with a 4.70 ERA. Recently he elected not to opt out of the final two years and $50 million of his deal.
Gausman, on the other hand, has been the best pitcher in the American League by fWAR since joining the Jays.
And then there’s the matter of José Berríos, who was acquired from the Twins at the previous trade deadline, and was set to reach free agency at the end of the 2022 season. Rather than allow him to walk, the Jays managed to sign him to a seven-year, $131 million contract extension—the biggest in club history, and an especially significant deal considering the Jays’ famous unwillingness to sign any pitcher for more than five years under Paul Beeston.
Now, obviously the Berríos deal looked ugly after year one, and may yet end up ugly again. And Kikuchi looked like a bust for the first year, and Yimi García’s best work was a year or two away. But, all things considered, this was a great haul, and an incredible feat of momentum-pushing when it really didn’t have to turn out that way at all.
Getting it absolutely bang on at the top of the free agent market, picking up some quality mid-tier pitchers, trading non-premium prospects for an All-Star calibre talent in a quantity-for-quality deal, and signing a massive extension with a vital player who is getting dangerously close to free agency? Sounds like a pretty good blueprint for an offseason to me.
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I really wanted to use the heading “Snell Ya Later” in a Stray Thoughts… post, but alas, this might be the only time I end up mentioning that transaction. Great pitcher. Would have been pleased to have him. But a guy who doesn’t go deep into games (he’s averaged less than 5 1/3 innings per start over his career) and frequently misses time (he's reached 30 starts in a season just twice in his career) never seemed like an ideal fit for a Jays club so thin in the bullpen and in terms of starting pitching depth, and that seems to especially value durability.
The pair of Cubans were represented by the same agency and signed on the same day. Curious!
Let's (try not to) Remember Some Guys...
Good stuff Stoeten, I quite enjoyed that stroll down memory lane.
Two's scorin'...ho ho ho how I missed that one. I legit spit took the first time I read that during the '16 season.