Where does Myles Straw trade rank among the Blue Jays' worst moves of the Atkins era?

The Toronto Blue Jays landed one of this offseason's big name free agents last Monday, bringing Anthony Santander north of the border to kickstart things.

But one move doesn’t negate a string of bad luck and questionable decision-making by the front office, and maybe no move has been more head-scratching than the trade to get Myles Straw from the Cleveland Guardians.

Yes, the main part of the deal was to acquire international bonus pool money, whichwe all believed was going to be used to sign Roki Sasaki. However, when Sasaki ultimately signed with the Los Angeles Dodgers, it was chided as a long-decided outcome. The Dodgers are even being accused of using Sasaki's free agency to steal proprietary information from other clubs.

Whether Toronto felt like something fishy was going on or not, we’ll probably never know, but it does make the deal for the international bonus pool money confusing, especially now that they are on the hook for Straw’s $13.8 million over the next two seasons. Toronto had to be savvier, and couldn't let themselves get baited into believing they had to bolster their Sasaki offer.

It certainly looks like it was a move that will not yield anything in return.

It’s also an awful look from an operations standpoint, as it made the Blue Jays look silly for not doing their homework and getting duped by someone outside the organization.

‘Where does the Myles Straw trade rank among the Blue Jays' worst moves of the Ross Atkins era?’

Jays Journal asked this question on Twitter, and trying to answer that question felt like inspiring experiment. After all, there have been a couple of these “bad look” moves that stand out during Atkins' time as Blue Jays GM.

November 18, 2016: Blue Jays sign Kendrys Morales to a three-year, $33 million deal.

The Blue Jays were coming off a second straight trip to the ALCS, but unfortunately fell short again, losing the series 4-1 to Cleveland.

They still had a load of talent in place for the 2017 season, and while it was a group that was getting older, it looked like the Blue Jays had the pieces to keep the competitive window open. However, there was a big misstep at the beginning of the offseason, and it actually set the wheels in motion for a rebuild.

Just two weeks after telling Edwin Encarnacion to go test the waters as a free agent, the Blue Jays signed Morales to be their primary DH and handcuffed themselves from being more flexible with their lineup.

There was a lot of frustration from fans at this point. Edwin was a fan favorite, and he had just hit a walk-off home run to win the AL Wild Card game.

He talked about wanting to return to Toronto, and so did his agent. But when the news of the Morales signing came, it pretty much closed the door on Edwin returning.

In two seasons, Morales hit 48 home runs with a .249/.318/.442 slash line and 103 OPS+. That’s not awful value for that price tag. However, it makes it look so much worse when Encarnacion, who was the same age as Morales and could play the field more flexibly than Morales, signed with Cleveland for three years and $60 million.

Encarnacion hit 70 home runs and slashed .252/.358/.490 with an OPS+ of 123 in two seasons with Cleveland. He then hit another 44 home runs over his final 153 big league games with Chicago, New York and Seattle, carrying an OPS+ of 115.

August 31, 2018: The Blue Jays receive Julian Merryweather from the Cleveland Guardians in exchange for Josh Donaldson.

Sending Donaldson to Cleveland for Merryweather made some sense, given the fact that Vladimir Guerrero Jr. was already in the system, and they were developing him at third base at the time.

However, Donaldson had one more MVP-caliber season after the trade, and was productive up until 2023. Considering the Jays didn’t get much from Merryweather and eventually moved Vladdy to first base, would it really have been too much to ask to sign a former MVP and fan favorite to a deal that would have let him retire as a Blue Jay?

Again, it was a move that signaled the Blue Jays were going into rebuild mode, and the short-lived “glory days” of 2015 and 2016 were shockingly over.

But what makes the optics around this deal look worse is that reports surfaced indicatingToronto also had a chance to trade Donaldson for a 22-year-old named Jack Flaherty from St. Louis, but nixed the deal.

The was also the highlight of a 2018 trade deadline that did nothing for the Blue Jays to help jumpstart the rebuild, outside of acquiring Santiago Espinal for Steve Pearce from the Red Sox, who turned into an All-Star for half a season.

The other deals that season were as follows:

July 26, 2018: The Blue Jays receive Brandon Drury and Billy McKinney from the New York Yankees in exchange for J.A. Happ.

July 26, 2018: The Blue Jays receive Chad Spanberger, Forrest Wall and (PTBNL) Bryan Baker from the Colorado Rockies in exchange for Seunghwan Oh.

July 31, 2018: The Blue Jays receive Jacob Waguespack from the Philadelphia Phillies in exchange for Aaron Loup.

August 4, 2018: The Blue Jays sell the player rights of Gio Urshela to the New York Yankees

August 31, 2018: The Blue Jays receive Demi Orimoloye from the Milwaukee Brewers in exchange for Curtis Granderson.

All of these players were free agents at the end of the year, but none of the trades did anything for the immediate or long-term future of the Blue Jays.

July 28, 2019: The Blue Jays receive Anthony Kay and Simeon Woods Richardson from the New York Mets in exchange for Marcus Stroman.

To preface this, the deal itself is a good one on paper. Two young pitchers who were highly touted within the Mets system for a guy who was going to be a free agent at the end of the season. Kay was New York's number four prospect and Woods Richardson was ranked sixth.

It’s, again, the optics surrounding the deal that hurt the Blue Jays front office in the public eye.

Trading Stroman, who was 28 at the time, when the team was already thin on the pitching side still remains one of the biggest ‘emotional’ moves that Atkins has made.

Stroman wasn’t shy about the Blue Jays tearing down the team since the winter before the 2017 season, and made it known that he felt the front office should be focused on competing instead. Atkins and Co. clearly didn’t like that. Perhaps they didn't want to be reminded of their shoddy July the year prior.

Yes, Stroman was going to be a free agent, but he had made it clear he was hoping to stay in Toronto…this sounds familiar, doesn’t it? A homegrown star, saying they want to stay, all while an extension never emerges.

Instead of extending him, the Blue Jays traded him (and then flipped one of those players in arguably Atkins’ best move to date). Adding insult to injury, they proceeded to start dealing for arms immediately at the next year's deadline.

November 16, 2022: The Blue Jays receive Erik Swason and Adam Macko from the Seattle Mariners in exchange for Teoscar Hernández.

Swanson was great in his first year as a Blue Jay, not so much his second year. Macko is picking up steam as an arm that might be worth watching in the system.

However, it is really hard to justify giving up a power bat in his prime years, in a division like the AL East, for a relief pitcher that probably could’ve been found on the market (or in a lesser trade).

It also stings to send a guy that had endeared himself to the fans, and who had just hit two home runs in a playoff game, to the team that just beat you in said playoff game. To watch Hernández come up clutch in a big market like LA in last year's postseason was also hard to watch as a fan.

You feel amazing for the guy. You just don’t love the uniform he’s doing it in.

Conclusion: Is the Myles Straw move worse than any of these?

At this point, it’s probably just as bad as not bringing back Encarnacion or not signing Stroman to a long-term deal.

However, this could all be a moot point by spring training if Toronto finds that that money owed to Straw doesn’t actually handcuff them from making other big moves.

They’ve also spent some of that international bonus pool money on some prospects, and who knows how they will turn out?

But, for the time being, they have another ‘glove-first’ guy who spent all but seven games in Triple-A last season.

There’s no doubt it isn’t a great move, but we have to give him kudos for the possibility that maybe the Sasaki failure was the…straw that broke the camel's back, and will lead to the Jays prospering before the season begins.