Biggest trade deadline deals in Toronto Blue Jays history

For the Toronto Blue Jays who rank fourth in the American League East, the firesale has already started.

Players like J.A. Happ and Seung-hwan Oh have already been parted with, while there may be more pieces being dangled in front of competitive ball clubs looking to add at the deadline as we speak.

Although none of the names that the Blue Jays have acquired this year have fans making a beeline to MLB Shop.com to pick up their shirsy, there were multiple times where that was the case.

Here’s your definitive ranking.

* Honourable mention: Blue Jays trade Steve Karsay and Jose Herrera to the Oakland Athletics for Rickey Henderson. 

Sure this trade was a big deal because the team got Rickey Henderson for crying out loud, but Henderson’s numbers with the Jays were nothing crazy, and he was only here for half a season.

10. 2012 – Blue Jays trade Eric Thames to the Seattle Mariners for Steve Delabar

The names of this deal may not jump out at you, but this trade has been pretty impactful.

Thames had a pedestrian second-half after being dealt to Seattle in 2012, which spurred him to play all of 2013 in the minors. The slugger afterward fled to the Korean Baseball Organization where he had great success. The first baseman was the 2015 KBO Most Valuable Player of the year, which sparked his return to MLB with the Brewers.

In his season and a half with Milwaukee, he has hit 44 home runs, along with an on-base percentage of .356.

Delabar, on the hand, was a very solid option for the Blue Jays out of the bullpen. In 2012 the righty posted a 3.38 earned run average, and in 2013 he dialed up a 3.22 ERA which helped send the reliever to the All-Star game. His fall off after those campaigns was quite significant, but nonetheless, he was a very useful tool for the team over a good chunk of time.

9. 1989 – Blue Jays trade Francisco Cabrera and Tony Castillo to the Atlanta Braves for Jim Acker

Like recently traded Jays pitcher J.A. Happ, Jim Acker had two stints with the Blue Jays. In his second tenure with the team when he was re-acquired from Atlanta in 1989, he made an instant impact.

Down the stretch for Toronto, the righty posted a 1.59 ERA over 28.1 innings pitched and was a very dependable arm for the team. In the ALCS against the Oakland Athletics, he appeared in all five games out of the bullpen. Despite dropping the series in five games, he produced a very respectable 1.42 ERA, allowing only one earned run.

Francisco Cabrera never wound up playing more than 70 games in a single season with the Braves and by 1993 Tony Castillo was back with the Blue Jays.

Although Acker was acquired in August, after baseball’s traditional non-waiver deadline, his reacquisition by the Jays still qualifies for this list, because it falls under the umbrella of “close enough.”

8. Blue Jays trade Paul Spoljaric and Mike Timlin to the Seattle Mariners for Jose Cruz

A long-time Blue Jay, Timlin served as a member of the team for seven years, which included being a member on both the 1992 and 1993 World Series teams. A solid season as the team’s closer in 1996 was followed by a bit of a lackluster year in 1997, and a chance to acquire an up-and-coming power hitter struck the Jays as an opportunity too good to pass up.

Coupling the right-hander with Canadian Paul Spoljaric, the team acquired 23-year-old Jose Cruz from Seattle.

The outfielder came in and was a great addition for the team over six seasons which included finishing second in AL Rookie of the Year voting in 1997, a pair of 30+ home run seasons, and a 2001 campaign which made him one of only three players that season who finished with 30 homers and 30 stolen bases.

Both Timlin and Spoljaric only lasted two seasons in Seattle. Spoljaric’s career did not inspire much as he was out of the league after 2000. Timlin, went on to win two more World Series rings as a member of the Boston Red Sox, finishing his career with four rings.

7. 2015 – Blue Jays trade Jesus Tinoco, Miguel Castro, Jeff Hoffman and Jose Reyes to the Colorado Rockies for LaTroy Hawkins and Troy Tulowitzki

There have been some serious ups and downs since Troy Tulowitzki has joined the Blue Jays. (Photo by Rob Tringali/SportsChrome/Getty Images)

In the history of the Blue Jays’ franchise, you could argue that the team has only ever acquired one player through trade who at one point of his career was widely considered the best player in baseball.

Troy Tulowitzki was that guy.

With the Jays powering through the dog days of the summer, Alex Anthopolous awarded the team at the time with the acquisition of the five-time All-Star. Tulowitzki was a fairly important piece to the Blue Jays’ 2015 and 2016 post-season runs, but, the move never fully panned out as expected.

After leaving the confines of Coors Field, Tulo has not fared better in a single major statistical category with his new team. He has hit for a far lower average (.250, down from .299), a lower on-base percentage (.313 down from .371), and has only appeared in 238 of a possible 463 games, which includes zero of the teams’ games this season.

Hawkins only played half a season in Toronto but was a solid veteran presence out of the bullpen for the team during his tenure.

Jeff Hoffman was the centrepiece prospect heading back to the Rockies in the trade. The first round pitcher has developed a little slower than expected and after a stint in the big leagues this year, has been demoted to the minors.

Jose Reyes only lasted a half-season in Colorado before moving onto the Mets, Miguel Castro is now a solid reliever for the Orioles, and Jesus Tinosco has not cracked a Major League roster.

6. 2015 – Blue Jays trade Matthew Boyd, Jairo Labourt and Daniel Norris to the Detroit Tigers for David Price

David Price solidified the Toronto Blue Jays’ starting rotation. (Cole Burston/Toronto Star via Getty Images)

When the Blue Jays acquired Tulowitzki from the Rockies, many thought that would be the final move GM Alex Anthopolous would make in 2015.

Those people were happily mistaken.

The current Atlanta Braves general manager and executive vice president saw that the perennial powerhouse Boston Red Sox and New York Yankees were a step behind their usual form in 2015, and took full advantage of that.

Even though he was only with the team for a cup of coffee, David Price was a great fit for the Blue Jays. After posting All-Star game worthy numbers prior to being dealt, the lefty produced even more effectively after coming north of the border with a lower ERA (2.30 from 2.53), a better WHIP (1.009 from 1.110), and far superior strikeouts per nine (10.5 from 8.5).

His post-season numbers, however, were not nearly as good as his regular season ones and that, unfortunately, would be Price’s last memory in Toronto before leaving for greener pastures, and a green monster in Boston.

Daniel Norris has been inconsistent as a Major League starter and is currently struggling with a groin injury. Matthew Boyd has been solid as a middle of the rotation starter for Detroit this season, and Jairo Labourt appeared in six games for the Tigers last season but has yet to make a big league appearance this year.

5. 1993 – Blue Jays trade Darrin Jackson to the New York Mets for Tony Fernandez

Tony Fernandez had four separate stretches with the Toronto Blue Jays. (Photo credit should read JEFF KOWALSKY/AFP/Getty Images)

Looking to load up for their second straight championship run, Toronto acquired Tony Fernandez to help shore up their infield.

A fan favourite, Fernandez spent eight seasons in Toronto before being shipped off to San Diego as part of the package to land Roberto Alomar. After missing out on the team’s first World Series run, he was around and played a big role the second time around.

A great player at the plate and a real solid defender, the team’s all-time games played leader batted at a clip over .300 in both the regular season and the playoff, including an OBP of .400 in the post-season also.

After 1993, Fernandez left for the Cincinnati Reds, but he returned to Toronto on two other occasions.

Darrin Jackson’s New York Mets career did not last long. The following season he was with the White Sox, and after two years in Milwaukee, finished his career in 1999 back in Chicago with the White Sox.

4. 1992 – Blue Jays trade Jeff Kent and Ryan Thompson to the New York Mets for David Cone

David Cone was one of the best pitchers of his time. (Credit: Stephen Dunn /Allsport)

Like the Acker trade, this one happened in August, but rules are meant to be broken, so this deal also makes the list.

Toronto wanted to stock their rotation up late in the season with another talented arm, and they got one of the best in baseball with David Cone.

After dominating the National League and qualifying for the All-Star game in 1992, the Jays added Cone in the middle of August. Despite switching leagues, the righty was just as dominant pitching on an extremely talented Blue Jays squad en route to winning his first of five World Series and was the starting pitcher for Game 6 of the Finals against the Braves, the series-clinching game.

While the Blue Jays won the Championship with Cone, Kent had a very impressive resume of his own. None of infielders best work occurred as a member of the Mets during his three-plus year tenure in New York.

Over the course of his 12-year career with the San Francisco Giants, Houston Astros, and Los Angeles Dodgers, Kent finished as a five-time All-Star, four-time Silver Slugger, and the 2000 NL Most Valuable Player.

3. 1986 – Blue Jays trade Doyle Alexander to the Atlanta Braves for Duane Ward

The Blue Jays have relied heavily on the strong right arm of reliever Duane Ward. (Photo by Jeff Goode/Toronto Star via Getty Images)

In 1986, the Blue Jays acquired one of the major pieces that would help them win back-to-back World Series in pitcher Duane Ward.

The righty was drafted as a first-round pick by the Atlanta Braves just four years prior to the trade and had struggled in the 1986 season. Keep in mind this was his first big league season, but he garnered a 7.31 ERA with Atlanta over 10 appearances.

Fast forward six years into the future though, and Ward was one of, if not the best arm the team had coming out of the bullpen and was one of the key components to the team’s World Series wins in both 1992 as a reliever, and 1993 as the closer.

Doyle Alexander never fully put it together for Atlanta but did make it to the All-Star game in 1988 with the Detroit Tigers.

2. 2009 –  Blue Jays trade Scott Rolen to the Cincinnati Reds for Edwin Encarnacion, Josh Roenicke, and Zach Stewart

Edwin Encarnacion was one of the most beloved Toronto Blue Jays thanks to his ‘Edwing.’ (Photo by Jon Blacker/MLB Photos via Getty Images)

Sure, Scott Rolen has an MLB resume that puts most others to shame, but the Cincinnati Reds did not make out as victors in this move.

Rolen, in his 15th MLB season, was showing signs of decline, and given his age and Toronto’s standing in the American League, was no longer a fit for the team’s plans. The Reds who were contenders in the NL were hoping the acquisition of the third basemen could help spark the team.

Although the veteran infielder still managed to qualify for a pair of All-Star games with Cincinnati, the team never made it past the Divisional Series with him on the squad during his three-plus year stint.

The Blue Jays only hit on one of the three pieces coming back their way, but my word did they knock it out of the park.

Edwin Encarnacion will undoubtedly go down as one of the best Toronto Blue Jays of all-time. The first baseman ranks top ten in Blue Jays history in home runs (239), slugging percentage (.522), extra-base hits (445), and runs batted in (679).

Not to mention, he provided one of the best moments in Blue Jays’ history.

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1. 2008 – Blue Jays trade Robinson Diaz to the Pittsburgh Pirates for Jose Bautista

Jose Bautista may be the greatest Toronto Blue Jay of all-time. (Photo by Andrew Dieb/Icon Sportswire via Getty Images)

Well, this trade did not work out very well for the Pittsburgh Pirates.

Robinson Diaz appeared in a grand total of 44 Major League games — Jose Bautista once hit 54 home runs in a single season, true story.

Clearly, I do not have to spell it out. Joey Bats is arguably the greatest Toronto Blue Jay of all-time, and the team, in hindsight, ransacked Pittsburgh to acquire his services.

Over the course of his tenure in Toronto, Bautista racked up six All-Star game honours, three Silver Sluggers, posted seven straight seasons of 20 home runs or more and holds the franchise record for most homers in a single season.

Plus, this bat toss was utterly ridiculous.

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