8 Blue Jays trade heists people don’t talk about enough

When it comes to trades, the Toronto Blue Jays as an organization have been heavily scrutinized for making some bad ones in recent memory. It just seemed like no matter what they do, they always ended up with the short end of the stick in the finalized deal.

Just for example, one of the most recent trades that has left a sour taste in the mouths of many Jays’ fans was the one that that sent top prospect Gabriel Moreno and fan favourite Lourdes Gurriel Jr. to the Arizona Diamondbacks for Daulton Varsho. Not only did Varsho struggle at the plate despite a strong defensive season, Moreno and Gurriel would end up leading the Diamondbacks right to the World Series and almost even won it all, making it quite the hard pill to swallow.

Going back even further, one of the more notable ones involved the legendary and late Roy Halladay. As perhaps one of the best pitchers to ever suit up in a Jays’ uniform, the Jays dropped the ball big time when they received an underwhelming package from the Philadelphia Phillies that included Kyle Drabek, Michael Taylor, and Travis d’Arnaud in exchange for the all-time great. Taylor was subsequently flipped to the Oakland Athletics for Brett Wallace. With the centrepiece of the package being Drabek, he ended up turning out to be a complete bust. Whereas for both Wallace and d’Arnaud, they actually developed into solid major leaguers, but with other teams. And of course, Halladay would help the Phillies go on two postseason runs, including becoming only the second pitcher ever to record a no-hitter in the postseason in the process.

But as much as it hurts to relive those painful moments, the Jays, believe it or not, have pulled off quite a bit of their own heists of other teams as well. Just as the saying goes, you win some, you lose some.

As a result, we will take a look at eight big trades that ended up heavily-favouring the Jays in the end that people don’t talk about enough. Perhaps by revisiting them now, it will help make us all feel better that the Jays actually won something for real.

Blue Jays acquire Juan Guzmán from the Los Angeles Dodgers for Mike Sharperson

With a pretty stacked lineup in the Jays’ contending season back in 1987, former first-round pick Mike Sharperson found himself to be one of the odd man out when he was traded in-season to the Dodgers for Juan Guzmán. The Jays had incumbents Garth Iorg, Nelson Liriano and Manuel Lee to fill Sharperson’s role adequately on the roster, so it gave the team some flexibility to look for some future pitching help.

Playing mainly in a utility role with the Dodgers, Sharperson just put up modest production numbers, averaging just 43 runs scored, 3 home runs and 36 RBI while hitting .280 over a 162-game schedule pace for his career. He was a part of the Dodgers’ 1988 championship winning team, but he played just a minor role as he ended up with only two postseason plate appearances. 

On the other hand, Guzmán provided the much-needed stability and impact in the Jays’ starting rotation the moment he made his MLB debut in 1991. He played a huge role in leading the Jays to three consecutive postseason appearances from 1991-1993 as he compiled a stellar 40-11 record with a 3.28 ERA, 1.28 WHIP, 482 strikeouts in 540.1 innings pitched in 84 starts over that time frame. More importantly, he was a beast when the games mattered most during the playoffs where he went 5-1 with a 2.44 ERA, giving up just 1 home run along with 41 strikeouts in 51.2 total postseason innings pitched. Guzmán eventually regressed somewhat in the following years, but there was no doubt without Guzmán, the Jays do not win back-to-back World Series in 1992 and 1993.

Blue Jays acquire Devon White, Willie Fraser, and Marcus Moore from the California Angels for Junior Félix, Luis Sojo and Ken Rivers

During the 1990-91 offseason, the Jays and the California Angels struck a deal that netted Toronto defensive wizard Devon White, with promising outfielder Junior Félix as the biggest name going the other way in a six-player swap. At the time, the Jays took a big gamble in giving up their young starting outfielder to obtain the proven defensive acumen of White. Although Félix had shown plenty of potential at the plate, he presented some deficiencies in the field with just a .966 fielding percentage.

For the Angels, Ken Rivers never ended up seeing a major league game, whereas Sojo had a more sustainable MLB career as a utility player after leaving California. For their main attraction in Félix, he would also end up leaving the Angels after two seasons after recording a career-high 72 RBI in 1992 with the club.

In contrast, White became a key cog in the Jays’ lineup in his five seasons with the ballclub. He officially gave the team a legitimate lead-off hitter that could hit for average and torment the opposition on the basepaths. On top of that, White also provided tremendous defensive stability in the outfield as exemplified by the Gold Glove Award that he won every single season with the Jays. In 656 games with Toronto, he batted .270 with 452 runs scored, 155 doubles, 34 triples, 72 home runs, 274 RBI and 126 stolen bases. In particular, he was exceptional during the Jays’ contending years in the early 1990s in helping the team to their two World Series titles. His defining moment was when he made an amazing leaping catch at the wall during Game 3 of the 1992 World Series against the Atlanta Braves that should have turned into a triple play, but was not to be. Nevertheless, it became one of the all-time magical moments to be forever etched into baseball history. Just almost that alone was enough to make the trade a 100% win for the Jays.

Blue Jays acquire José Bautista from the Pittsburgh Pirates for Robinzon Díaz

Perhaps the biggest trade heist in Jays’ history, no one should ever forget how we managed to get José Bautista in our hands. Back in 2008, third baseman Scott Rolen was dealing with a shoulder injury and the Jays needed a temporary solution in the meantime. As a middling player for the Pirates at the time that could play various positions in the field, Bautista caught the eye of the Jays’ management as someone that could fill in at third. Because of his flexibility, Bautista could then move to other positions and play the role as an utilityman when Rolen was good enough to resume his duties.

As a result, they put in the claim for Bautista, who was placed on revocable waivers in August that very year by the Pirates. In the end, they worked out a trade that involved catching prospect Robinzon Diaz going the other way. For Diaz, he would go on to appear in only 43 games for the Pirates while spending the rest of his career in the minor leagues. In the case for Bautista, he became the superstar the new generation Jays sorely needed at the time and brought the team back into significance.

In his 10 seasons with Toronto, Bautista hit .253 with an .878 OPS, 136 OPS+, 790 runs scored, 288 home runs, 766 RBI, 803 walks and 948 strikeouts in 1235 career games played. In doing so, he became a six-time All-Star, a three-time Silver Slugger award winner, along with being an AL MVP finalist in 2011. More importantly, without Bautista, we wouldn’t have what will go down as one of the biggest moments in Blue Jays’ playoff history with his bat-flip home run heard around the world in Game 5 of the ALDS against the Texas Rangers in 2015. He is now enshrined on the Jays’ Level of Excellence and has become an icon in Toronto that will never be forgotten.

Blue Jays acquire Edwin Encarnación, Josh Roenicke and Zach Stewart from the Cincinnati Reds for Scott Rolen

On paper, the transaction doesn’t really appear to be as lopsided as it looks, with a superstar Hall of Famer going one way in exchange for three promising players with potential going the other way. However, it was what transpired in the years following the elusive trade in 2009 that has made this one of the Jays’ all-time trade steals.

Despite not being in the playoff hunt at the time, the Reds were looking to add a veteran presence to their lineup to help lead their young core to success down the road. When the Jays made Scott Rolen available due to his waiving of his no-trade clause, the Reds got their man while the Jays received three potentially useful pieces in return. Rolen would pay off somewhat for the Reds in the following three years, as he led the team to the playoffs for two of them. However, his overall production fell off considerably following his 2010 season.

For both Josh Roenicke and Zach Stewart, they eventually turned into side notes after their short tenure with the club. On the other hand, Edwin Encarnación would go on to become one of the main offensive catalysts for the Jays for over half a decade despite an initial setback after joining the team. He was named an All-Star in three of those seasons, along with averaging close to 38 home runs and 110 RBI each year in his prime. In eight seasons with the team, Encarnación hit .268 with an .878 OPS, 239 home runs and 679 RBI in just one game shy of 1000.

Jays fans had the luxury of seeing him “carry the parrot” in his home run trots for many game-changing moments. Most noteworthy was his memorable walk-off three-run blast in the bottom of the 11th inning to help the Jays prevail over the Baltimore Orioles in the 2016 AL Wild Card Game. In doing so, he has become one of the best players to have played for the Jays in recent memory as a result, which has made the surprising trade off of Rolen a huge steal for the team in the end.

Blue Jays acquire Josh Donaldson from the Oakland Athletics for Brett Lawrie, Franklin Barreto, Kendall Graveman and Sean Nolin

When it comes to instant impactful trades that the Jays have made this century, one of the key ones that quickly come to mind is the blockbuster involving the recently retired Josh Donaldson during the 2014-15 offseason. With the Jays desperately wanting to get back into the postseason picture after almost a two-decade absence, they made the bold move in acquiring the budding superstar from the Oakland Athletics in exchange for a plethora of prospects that included Canada’s very own Brett Lawrie.

Lawrie was also a budding star in the making at the time, but just not at the calibre of Donaldson yet. So it was indeed a risk for the Jays, not to mention they threw in another three promising young players on top of it. Fortunately, the daring move paid off big time as both Franklin Barreto and Sean Nolin failed to reach their full potential, while Lawrie never developed into the superstar that was expected of him and was actually out of MLB baseball after the 2016 season. Kendall Graveman was the only one that materialized into a future bullpen stud; however, it occurred way after he left the Athletics’ organization, leaving Oakland nothing to show for as a result of the trade.

In the case for the Jays, they ended up with not only a two-time All-Star and Silver Slugger winner, but the 2015 AL MVP as well to boot. Donaldson may have only stayed for less than four seasons, but his overall contributions will forever be remembered in more ways than one. Over 462 career games with Toronto, he batted .281 with a stellar .931 OPS, 148 OPS+, 116 home runs and 316 RBI. His most marquee moment in a Jays’ uniform was his “Donaldson Dash” to score the winning run in Game 3 of the 2016 ALDS to sweep their nemesis the Texas Rangers in three games. More importantly, despite the Jays having both the dynamic duo of Bautista and Encarnación together already for many seasons prior, the team never seemed to be able to get over the hump to reach the playoffs until Donaldson’s eventual arrival in 2015. Therefore, what hasn’t been talked about enough is not the huge steal that Donaldson was, but his ultimate impact that took the team to the next level and beyond.

Blue Jays acquire David Price from the Detroit Tigers for Daniel Norris, Matthew Boyd and Jairo Labourt

Back during the Jays’ contending years in 2015 and 2016, the GM at the time in Alex Anthopoulos was heavily criticized for emptying the farm system in exchange for just a “chance” at a championship in an “all-or-nothing” mentality. When the Jays eventually headed into a rebuild starting from 2017, many believed that was a by-product of those moves that were made. 

But when it comes to the huge trade at the 2015 deadline in which the Jays acquired Cy Young winner David Price from the Tigers for three of their top prospects in the system, that particular one actually turned out to be the right move in the end. With the Jays hovering around a .500 record at the time but still within reach of a playoff spot, the addition of Price became a huge game-changer for the club. He practically single-handedly put the Jays on his back and carried them into the postseason by pitching to a sparkling 9-1 record with a 2.30 ERA, 1.01 WHIP, with 87 strikeouts in just 74.1 innings of work down the stretch.

On the other hand, as a former second round pick in the 2011 MLB Draft and number one prospect in the Jays’ organization, Daniel Norris turned out to be quite the disappointment, with a career ERA close to 4.70 and WHIP close to 1.40 WHIP while moving about around the league in recent years. Similarly for Matthew Boyd, he had a couple serviceable years with the Tigers, but is currently without a team for the 2024 season. Finally, Jairo Labourt only saw six games in total at the major league level, and was entirely out of baseball by 2018. That has certainly made Anthopoulos’ gamble much more palatable in the end. Price’s stay with the Jays may have been short-lived, but he helped inspire the winning culture in their clubhouse that eventually carried through for another season in 2016. Nevertheless, his joyous smile and his love for popcorn at Rogers Centre will always be remembered.

Blue Jays acquire Teoscar Hernández and Nori Aoki from the Houston Astros for Francisco Liriano

With the Jays preparing a rebuild as a result of a huge down year following their 2016 postseason run, they traded away one of their key acquisitions from the previous year in pitcher Francisco Liriano to the contending Houston Astros for Nori Aoki and a power-hitting prospect at the time in Teoscar Hernández at the 2017 trade deadline. The Astros looked to Liriano to be their experienced lefty out of the bullpen down the stretch; however, he sputtered to a 4.40 ERA and 1.67 WHIP in 20 appearances and was subsequently not retained following the end of the 2017 season.

Aoki was never much in the rebuilding plans for the Jays, as he was eventually granted his unconditional release towards the end of August. So if the Jays were to recoup anything coming out of the trade, it would have to come from the hidden potential of Hernández. However, one of the key flaws to Hernández’s game despite his enormous power was the fact that he was prone to the strikeout, leading to a low batting average and limiting his effectiveness in the process. 

Thankfully, Hernández eventually evolved into the impact power producer that he is today by raising his average to respectable levels, even though his whiffs still remained an issue. As a result of his slight adjustment, he became a two-time Silver Slugger, along with becoming a first-time All-Star while batting in the heart of the lineup for the Jays for the majority of his six seasons with the club. In 609 games, Hernández hit a solid .263 with an .823 OPS, 129 home runs and 369 RBI, with many of it coming in key situations over the years. In doing so, he was a critical part of the wave of young talent that brought the Jays back into contending status at the start of this current decade. So compared to the negligible two months that Liriano ended up spending with the Astros, let’s just say the Jays won this one in a landslide.