Blue Jays' best and worst moves under Mark Shapiro and Ross Atkins

The Toronto Blue Jays have been through a lot since Mark Shapiro and Ross Atkins were hired to run the front office back in 2015.

Toronto kicked off the new era with a successful 2016 season that saw it reach a second-consecutive American League Championship Series. The club took a downward turn from there, sputtering along in 2017 and '18 before fully embracing a rebuild.

The 2019 season featured a lot of losing, but also marked the arrival of Vladimir Guerrero Jr. and Bo Bichette. In 2020, the Blue Jays proved they were ahead of schedule and took advantage of an expanded playoff field in the pandemic-shortened campaign to grab a taste of the postseason.

That brings us to 2021. Toronto piled up an impressive 91 wins, but that record left the team one game short of a playoff spot and was only good for fourth place in the ultra-competitive American League East.

To summarize, over the past six years Shapiro and Atkins have been at the helm of a World Series contender, a declining team, a rebuilding club, and a young group back on the upswing. They've made a number of transactions over that period of time, with some of them being great successes, and others being huge flops.

So, equipped with the benefit of hindsight, here's a look at their best and worst acquisitions with the Blue Jays so far. We've excluded the recent blockbuster signings of Hyun-jin Ryu, George Springer, Jose Berríos and Kevin Gausman since the jury is still out on how those moves will play out down the road. Perhaps they'll appear in a future version of this list.

Best Moves

Trading for and re-signing Robbie Ray

Ray had shown flashes of brilliance over his career with the Arizona Diamondbacks, but a terrible start to the 2020 season gave the Blue Jays a chance to buy low at the trade deadline.

After making slight improvements after the trade, the left-hander re-signed with the Blue Jays shortly after free agency opened that winter, inking a one-year, $8-million prove-it deal. And boy, did Ray prove it.

The 30-year-old won the American League Cy Young award in 2021, logging a sparkling 2.84 ERA with a league-best 248 strikeouts. He also drastically improved his walk rate.

That dominant form resulted in the Seattle Mariners luring him to the west coast with a five-year, $115-million contract.

Signing Marcus Semien to a prove-it deal

Ray and Semien were the biggest bargains of last offseason, and the Blue Jays landed both of them.

After finishing third in MVP voting in 2019, Semien saw his production dip in 2020. Toronto sensed an opportunity, and brought him aboard on a one-year, $18-million deal. Semien rewarded the club with another MVP-calibre season in which he broke the MLB record for most home runs by a second baseman.

Like Ray, Semien parlayed his success into a huge contract, inking a seven-year $175-million pact with the Texas Rangers.

Landing Teoscar Hernández from Houston

There wasn't a lot of good that came out of the Blue Jays' 2017 season, but their trade with the Astros to bring in Hernández was a highlight. Toronto sent Francisco Liriano to Houston in the deal, and acquired a core piece of the franchise in return.

It took a while for Hernandez to realize his potential, but he's turned in back-to-back Silver Slugger-winning seasons and has become a staple in the middle of the Blue Jays' lineup. Houston went on to win the World Series in 2017, but Liriano did not play much of a role.

Adding Cimber and Richards in bullpen makeover

If you had to choose one reason why the 2021 Blue Jays missed the playoffs, it would be because of a leaky bullpen that cost them numerous games over the first few months of the season.

Shapiro and Atkins decided to strike well before the trade deadline to address this glaring area of need, bringing in relievers Adam Cimber and Trevor Richards in late June and early July, respectively. Both deals paid off, but the Cimber deal was particularly strong. Toronto reeled in Cimber and serviceable outfielder Corey Dickerson from the Marlins in exchange for Joe Panik and a minor-leaguer.

Cimber and Richards each have multiple years of control left on their contracts, so these trades could yield even greater dividends in the future.

Reuniting with J.A. Happ against popular opinion

Atkins wasn't in place for this move, but one of the first big signings under Shapiro was a reunion with Happ in November of 2015. The transaction was criticized at the time, as many fans clamoured for the club to bring back ace David Price.

Happ wasn't the flashy name Blue Jays fans wanted, but the three-year, $36-million contract turned out to be a steal. The southpaw posted ERAs of 3.18, 3.53 and 3.65 over the life of the deal, earning an all-star nod in 2018 before being sent to the Yankees at the trade deadline (more on that later).

Worst Moves

Letting Encarnación walk and replacing him with Morales

Few players in Blue Jays history have captured the heart of fans like Edwin Encarnación. The Dominican slugger "walked the parrot" 239 times over his eight-year run in Toronto and was instrumental in the club's successful 2015 and '16 campaigns.

So when Atkins and Co. moved on from the franchise icon within a few weeks of free agency opening in the 2016 offseason and replaced him with a declining Kendrys Morales, it ruffled some feathers. Morales inked a three-year deal and posted an underwhelming .760 OPS during his Blue Jays tenure. He was traded, along with cash considerations, to the Oakland Athletics right before the start of the 2019 season. Simply put, the deal was a bust.

Encarnación delivered OPS numbers of .881, .810 and .875 with 104 homers over that same three-year period.

Not getting anything significant for Happ

As mentioned above, Happ was an extremely steady presence for the Blue Jays' rotation and returned excellent value at $12 million per year.

So when it came time to trade the veteran during the ugly 2018 season, it would have been reasonable to expect Toronto to get something decent in return. The Blue Jays were clearly on the rebuilding path, so a prospect-based deal would have made the most sense. Even if teams weren't willing to part with a blue-chip piece in exchange for a rental, the Blue Jays could have sought out some higher-risk "dart-throw" type prospects with the hopes of hitting on one.

Instead, the package the Blue Jays received from the New York Yankees curiously featured a pair of MLB-ready, lower-ceiling players in Brandon Drury and Billy McKinney. Drury hit .208 with a .606 OPS over parts of three years in Toronto, while McKinney hit .230 with a .730 OPS over the same time frame. Both players were designated for assignment before the end of the 2020 season.

Selling Donaldson for pennies on the dollar

If the return for Happ seemed disappointing, what the Blue Jays received for former MVP Josh Donaldson was even worse.

Donaldson followed up his spectacular 2015 campaign with similarly incredible numbers in 2016 and '17. Again, with a rebuild clearly in store, the Blue Jays would have been wise to maximize the value of their greatest asset and sell him ahead of the 2018 season. It was reported that the Blue Jays turned down a trade offer that winter from the Cardinals that featured Jack Flaherty, who has developed into a front-of-the-rotation arm.

Toronto opted to hang on to Donaldson to begin 2018, and the worst-case scenario struck. Injuries limited the star to just 36 games with the Blue Jays that year, and when he was in the lineup he slashed a meagre .234/.333/.423 with five home runs.

With his value significantly diminished, Donaldson was eventually shopped to Cleveland in exchange for a player to be named later, who turned out to be Julian Merryweather. The 30-year-old right-hander has flashed electric stuff in relief, but constant injuries have resulted in him logging just 26 total innings at the MLB level over the past two seasons.

Even if Merryweather puts it all together and manages to stay on the field, the trade has to be considered a massive failure considering what the Blue Jays could have acquired had they made the logical move and pulled the trigger on a Donaldson deal earlier.

The Tanner Roark debacle

Roark was the definition of reliable from 2017-19. He wasn't going to wow you with his production, but you knew he would give you 30 starts per year and provide solid innings.

It turns out that assumption was wildly inaccurate. Roark signed a two-year, $24-million deal ahead of what ended up being an abbreviated 2020 season, and immediately saw his performance fall off a cliff. The veteran righty pitched to a 6.80 ERA over 11 starts in 2020, then followed it up with a 6.43 ERA in his first three outings of 2021.

With Roark legitimately unplayable, the Blue Jays designated him for assignment at the end of April. The diesel engine conked out.

Watching Urshela blossom with a division rival

To be fair to Shapiro and Atkins, there was no indication that trading Gio Urshela to the Yankees would be a move of significance. But hindsight is 20/20.

Urshela was nothing more than a depth infielder for the Blue Jays in 2018, splitting his time between the big club and the triple-A Buffalo Bisons. One season later, the native of Colombia was thriving in an everyday role for the Bronx Bombers and he hasn't looked back. He's hitting .292 with a .815 OPS over his Yankees career and offers defensive versatility in the infield. Consider him the one that got away.

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