Blue Jays: In hindsight, the worst trades that weren’t made

After the front office failed to capitalize on Josh Donaldson’s trade value, many fans are critical of how things went down. What other trades has the franchise “missed” on making over the years?

The Josh Donaldson trade is going to be something that’s debated among Blue Jays fans for years, regardless of how the rest of his, or Julian Merryweather‘s careers finish out. It would help if Merryweather became a solid rotation piece, and/or Donaldson didn’t return to being an MVP calibre player, but the complaining will persist regardless.

To some degree that’s understandable, but fans must also remember that hindsight is 20/20 and when Mark Shapiro and Ross Atkins elected to keep their star third baseman and give competiting a shot in 2018, I was admittedly in favour at the time. As we all know now, trading him last winter would have been the far better idea, but that sorta thing happens in baseball, unfortunately.

Not moving Donaldson earlier has had me thinking back to other periods in franchise history when the front office didn’t go through with a trade that was reportedly on the table. Sometimes we’re thankful those trades never  happened, but others, like in the case of the Blue Jays reportedly missing out on a chance to get Jack Flaherty from the Cardinals last winter, are a little more difficult to swallow.

It’s not the first time that’s happened in franchise history though, so let’s have a look back at some of the worst deals that never happened, and think about what could have been if things had gone a little differently.

Hard one to criticize, but…

The Blue Jays won the 1993 World Series, so that is the ultimate trump card, and I’ll never believe they should have done something differently that year based on how it worked out in the end.

But man, this one was a doozy.

Back at the trade deadline in ’93, then-GM Pat Gillick was working on bolstering the team for an attempt at a championship repeat, and he managed to do that by bringing in Rickey Henderson to strengthen the outfield and lengthen the lineup. The Blue Jays traded young prospect Steve Karsay as the centrepiece, a move that worked out well for them.

That said, there was another deal on the table at the time with the Seattle Mariners. The trade would have brought Randy Johnson to Toronto, who was already a star in the big leagues, but hadn’t fully established his Hall of Fame resume yet. With all due respect to Ricky, landing Randy Johnson would have been a franchise altering move, and might have extended the Blue Jays’ championship window as Johnson was under contract control until 1998. More of the story can be found here, but the long and the short of it was that Gillick had a deal with the A’s for Henderson first, and kept to first word even after the Mariners agreed to send Johnson to Toronto.

Again, you can’t really criticize a trade that ultimately helped lead to the second championship in franchise history, but I don’t think you’d find a Blue Jays fan that wouldn’t have loved to see Johnson in Toronto.

On the plus side, Karsay didn’t turn into the rotation stud that everyone thought he would, so the Blue Jays didn’t get burned on both ends after Henderson left as a free agent. It all worked out just fine, even if it’s a tough one to think about.

Arguably J.P. Ricciardi’s biggest blunder

The Blue Jays were struggling in the early 2000’s, and they had a few MLB pieces that made sense to trade at the time. One of those was Jose Cruz Jr. who was scheduled to be a free agent at the end of the 2002 season. He hadn’t panned out the way the Blue Jays thought he might in Toronto, slashing .245/.317/.438 in that final season.

There was a deal on the table that almost happened, and I’m sure that Ricciardi still thinks about from time to time. The New York Mets were interested in bringing Cruz to their contending squad, and offered a package around a talented prospect by the name of David Wright.

Again, trading Cruz made sense at the time because of his pending free agency, and the fact that the Blue Jays were well out of contention at the trade deadline, finishing July 18.5 games back. Ricciardi inexplicably held on to Cruz and didn’t offer him arbitration that winter either though, losing him for nothing when the Blue Jays would have had an infield captain for the next decade or more.

Wright only went on to be a best players ever to play for the Mets, and will finish up his career later this month when he plays in their final game to wrap up his historic career after rehabbing injuries for the last three years. Still, he had some very productive campaigns, and the one they call “Mr. Met” would have locked pretty good in a Blue Jays’ uniform.

Ricciardi was quoted at the time saying, “I’m not trading a major league player for some guy in the Sally League.”, and I’m willing to bet he’s had a bit of a change in philosophy since then.

Oh, what could have been.

Marcus Stroman to the Cubs?

This one is as much speculation on my part as it is fact, but it’s an interesting one to dream on. Let me also say right off the hop that I’m a fan of Marcus Stroman and I think he’ll be an important piece of the Blue Jays rotation for at least the next couple of seasons, if not beyond that.

However, there was a time when the Cubs were pursuing him pretty hard in 2017, at least before they acquired Jose Quintana from the White Sox. The prospect package was a big one that was sent across town in Chicago, and right now I’ll bet the Blue Jays would like a mulligan on trade discussions, even if they still like Stroman as a Blue Jay.

At the time there were rumours that the Blue Jays were looking for a strong MLB player, and likely one from the Cubs’ roster. That could have included someone like Kyle Schwarber, Ian Happ, or maybe even Addison Russell or Javier Baez (prior to his big breakout). The deal never did grow big legs, but it’s what the White Sox got back in return that makes me wonder if the Blue Jays didn’t miss out here.

The Cubs sent a prospect package to the White Sox that was headlined by Eloy Jimenez, perhaps the second best hitting prospect in baseball after Vladimir Guerrero Jr. The package also included pitcher Dylan Cease, first baseman Matt Rose, and infielder Bryant Flete. Jimenez and Cease were number one and two in the Cubs system at the time, and both figure to be a big part of the White Sox rebuild.

Jimenez in particular was sensational this season hitting .337/.384/.577 with 22 home runs, 75 RBI, and 28 doubles in 108 games split between Double and Triple-A. He caused a stir among White Sox fans similar to the way Vlad Jr. did when he wasn’t called up this fall, as the White Sox will look to keep him under club control for awhile as well. Cease was also fantastic between High A and Double-A, sporting a 2.40 ERA in 23 starts. Meanwhile, Stroman struggled through injury and ineffectiveness in 2018, arguably having his worst season as a pro.

Again, it’s not that trading away Stroman is something the Blue Jays definitely should have done, it’s more about what they could have landed from the Cubs. The idea of adding Jimenez to a minor league stable that already includes studs like Guerrero, Bo Bichette, Danny Jansen, and Cavan Biggio would have made a pretty unstoppable lineup. The Blue Jays should have that anyway, but it’s always fun to dream about adding another powerful bat to the mix.

Hopefully Stroman will regain his form in 2019 and either become the rotation leader that he’s capable of for the next generation of Blue Jays, or bring back a similarly valuable return in a trade sometime in his final two years of contract control in Toronto. I’ll reiterate one more time, I’m a fan of the Blue Jays pitcher, I just hope he can find his form again so we’re not talking about this for years to come.

Trading Bautista at the 2016 deadline?

I’m including this one even though I probably shouldn’t bother. To me and several baseball writers that I respect a great deal, the whole thing seemed ridiculous at the time, and still does, really.

However, there were rumours that the Blue Jays were exploring the idea of trading Jose Bautista back in 2016. Yes, in their second year of their playoff run, which also happened to be the final year of the contract he was playing on at the time.

There were plenty of rumours bouncing around the league, and it made sense that rival GMs would be calling to see if he was available. However, there was no way the Blue Jays were going to move their franchise icon in the middle of another year they were trying to win the World Series, not unless the return was a slam dunk. Even then, they needed Bautista to approve a trade, something that wasn’t going to happen unless it made a ridiculous amount of sense for the veteran.

There were even rumours of Bautista heading to the Washington Nationals in exchange for Max Scherzer. If that was true, the Blue Jays made a huge mistake in not taking that deal, although again, it’s hard to imagine that it was ever close to actually happening, and they needed Bautista’s approval to make a deal anyway.

The one part of trading him that would have made sense is the way things ended for “Joey Bats” in Toronto. He rode off into the sunset as a still-beloved player, but his story didn’t end the way anyone wanted to see it go in Toronto. Maybe everyone would have been better off if he had been traded in 2016, although it’s hard to imagine the playoff run and postseason without him kicking around, even if the iconic home run came a year earlier.

Roy Halladay almost ended up in L.A.

Back in 2009 the Blue Jays had accepted their fate in the AL East, and had resolved themselves to the fact that they were going to have to trade Roy Halladay. They did the same with Scott Rolen that July, and likely would have done the same with “Doc” had things gone the way that J.P. Ricciardi had planned.

There were multiple reports surfacing that talks got very close before the deadline, with the most commonly linked names being one of Jered Weaver or Joe Saunders, Erick Aybar, and outfield prospect Peter Bourjos. Weaver was the best of the bunch as far as career accolades, earning three straight top-5 finishes in Cy Young voting, and annual All-Star appearances from 2010-2012.

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The trade that didn’t help was re-lived well by Ian Hunter of bluejayshunter.com, and apparently fell apart because the Angels weren’t willing to part with Aybar in addition to the other pieces discussed. It’s hard to say if Halladay would have been the difference maker or not for those Angels teams, but he definitely would have given their rotation a boost regardless of what the trade package in return had been.

It’s not that this return is overly spectacular for someone like Halladay, however, when you compare it to what they eventually got from the Phillies then it looks a lot more appealing. The trickle down effect would have been interesting as well, as Aybar would have negated the need for a shortstop, and maybe Troy Tulowitzki never comes to town. The Blue Jays also got Travis d’Arnaud back in the Halladay trade, who was later a key piece that went to New York for R.A. Dickey. The rabbit hole is pretty endless on this one.

Most of the time it’s fun to think about “what could have been”, but in the case of Josh Donaldson’s recent trade, and with most of the examples I’ve listed above, it’s more painful than it is enjoyable.