Blue Jays: Best trades in franchise history

TORONTO, CANADA - OCTOBER 8: Troy Tulowitzki #2 of the Toronto Blue Jays and Edwin Encarnacion #10 and Jose Bautista #19 and Josh Donaldson #20 stand for the playing of the Canadian anthem during lineup introductions before the start of action against the Texas Rangers in Game One of the American League Division Series during the 2015 MLB Playoffs at Rogers Centre on October 8, 2015 in Toronto, Ontario, Canada. (Photo by Tom Szczerbowski/Getty Images)
TORONTO, CANADA - OCTOBER 8: Troy Tulowitzki #2 of the Toronto Blue Jays and Edwin Encarnacion #10 and Jose Bautista #19 and Josh Donaldson #20 stand for the playing of the Canadian anthem during lineup introductions before the start of action against the Texas Rangers in Game One of the American League Division Series during the 2015 MLB Playoffs at Rogers Centre on October 8, 2015 in Toronto, Ontario, Canada. (Photo by Tom Szczerbowski/Getty Images)
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TORONTO, CANADA – OCTOBER 8: Troy Tulowitzki #2 of the Toronto Blue Jays and Edwin Encarnacion #10 and Jose Bautista #19 and Josh Donaldson #20 stand for the playing of the Canadian anthem during lineup introductions before the start of action against the Texas Rangers in Game One of the American League Division Series during the 2015 MLB Playoffs at Rogers Centre on October 8, 2015 in Toronto, Ontario, Canada. (Photo by Tom Szczerbowski/Getty Images)
TORONTO, CANADA – OCTOBER 8: Troy Tulowitzki #2 of the Toronto Blue Jays and Edwin Encarnacion #10 and Jose Bautista #19 and Josh Donaldson #20 stand for the playing of the Canadian anthem during lineup introductions before the start of action against the Texas Rangers in Game One of the American League Division Series during the 2015 MLB Playoffs at Rogers Centre on October 8, 2015 in Toronto, Ontario, Canada. (Photo by Tom Szczerbowski/Getty Images) /

The Toronto Blue Jays have made a plethora of trades since their inception in 1977, some more memorable than others.

A laundry list of prominent players has come and gone throughout the team’s history that were acquired via the trade route.

Last week, Jays Journal featured an article recapping the “Worst Trades” in history so it only seemed appropriate to highlight some of the best deals that have occurred over the last 40+ seasons in Blue Jays land.

The Blue Jays have acquired a Hall of Famer, an MVP, and a home run champ all from acquisitions with other teams. The brain trust also shed an insurmountable amount of money in one of the slickest trades in Blue Jays history.

Some trades that didn’t make the list but are worthy of a mention include the acquisitions of Devon White and Duane Ward. So without further ado and in no particular order, here are some of the best trades in Toronto Blue Jays franchise history.

More Articles About Blue Jays Trade History:

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TORONTO, ON – JULY 25: Josh Donaldson
TORONTO, ON – JULY 25: Josh Donaldson /

November 28th, 2014- Blue Jays acquired Josh Donaldson From the Athletics In Exchange For Brett Lawrie, Franklin Barreto, Kendall Graveman and Sean Nolin

After a respectable 83-win season in 2014, the Toronto Blue Jays went ahead and added to their offense that already ranked top five in the majors in runs scored and home runs as well sixth in on-base percentage.

In late November the Blue Jays added a player many viewed as untouchable when they acquired Josh Donaldson in exchange for Brett Lawrie, pitching prospects Kendall Graveman and Sean Nolin as well as infield prospect Franklin Barreto.

Donaldson had just finished top-eight in AL MVP voting in back-to-back seasons and was just turning 29 as the Blue Jays had their core three in place and the baseball world marveled at the power in the heart of their order. Edwin Encarnacion, Jose Bautista and now Josh Donaldson. The Jays entered 2015 with three players who finished the previous season top ten in AL home runs and no other club had more than one.

Donaldson lit a fire in Toronto, much like his style of play, and his hustle never went unnoticed or unappreciated. Proof of this, a play Jays supporters won’t soon forget came in a 1 p.m. game on a Wednesday when he soared into the Tropicana Field seats, making a fully extended grab in the second row to keep Marco Estrada’s no-hitter intact with five outs remaining.

Thanks to Donaldson, the Blue Jays had found their swagger in 2015 backed by his American League MVP and he reintroduced the city of Toronto to October baseball as they won the AL East, ending a 21-year postseason drought. They eventually lost in the ALCS and would do so again the following year, but the baseball world was finally taking Canada’s team seriously again. They even appeared on the cover of Sports Illustrated with the headline, “The New Jacks.”

Donaldson would also go on to win two Silver Sluggers and appear in two All-Star games during his tenure. He had an injury-riddled 2018 before he was shipped off to Cleveland in August but during his first three years in Toronto, his WAR was the second best in baseball among position players behind only Mike Trout.

It was one of the best three year stretches in a Blue Jays uniform and Donaldson appeared in 136 more games during those seasons than the four other players in the deal would play in Oakland (through 2018).

Neither Lawrie or Nolin have played in a major league game since 2015 and Barreto is still only 22, appearing in 57 games with the A’s so far. Oakland hopes for some future production from Barreto as the only other player in the deal, Graveman, will likely miss all of 2019 rehabbing from Tommy John Surgery. Graveman has provided the team with the most value in this deal so far, pitching 441.1 innings over four seasons with a 4.38 ERA.

Donaldson has since reunited with the man who brought him to Toronto, Alex Anthopoulos, signing a one-year, 23-million dollar contract this offseason with the Braves. With the Blue Jays in rebuild mode, some fans may be hoping for a parade in Atlanta this fall.

Jays Journal Contributor: Cam Black-Araujo

TORONTO, ON – OCTOBER 9: Edwin Encarnacion #10 of the Toronto Blue Jays celebrates after hitting a two run home run in the first inning against the Texas Rangers during game three of the American League Division Series at Rogers Centre on October 9, 2016 in Toronto, Canada. (Photo by Vaughn Ridley/Getty Images)
TORONTO, ON – OCTOBER 9: Edwin Encarnacion #10 of the Toronto Blue Jays celebrates after hitting a two run home run in the first inning against the Texas Rangers during game three of the American League Division Series at Rogers Centre on October 9, 2016 in Toronto, Canada. (Photo by Vaughn Ridley/Getty Images) /

July 31st, 2009: Blue Jays acquired Edwin Encarnacion, Josh Roenicke and Zach Stewart To The Reds For Scott Rolen

It’s not the trade we’re accustomed to seeing with just under an hour until the non-waivers trade deadline as both the Reds and Blue Jays were ten or more games back from their division leaders at the time.

The Blue Jays shipped out league veteran, Scott Rolen, to Cincinnati in exchange for Edwin Encarnacion as well as pitchers Josh Roenicke and Zach Stewart. Roenicke and Stewart pitched a combined 53.1 innings for the Blue Jays and neither has pitched in the big leagues since 2013. Thankfully for the Toronto faithful, that Encarnacion player in the trade provided them some production and he reminded them of that every time he would tour the bases, arm out as if he was carrying parrot around the bases with him.

Encarnacion, a third baseman at the time of the trade, would go on to become one of the Blue Jays all-time greats during a time that rejuvenated a city, or even a country, that hadn’t truly seen winning philosophy from its team since the early 1990’s. He went on to hit 239 home runs for the Jays, third-most all-time, as well as 697 RBI’s over 999 games with the club, headlined by three All-Star appearances.

More importantly to everyone involved with the Blue Jays though, he was part of the core that would provide the club with back-to-back births in the ALCS.

The Reds would also get some production from Rolen throughout the final three years of his career, despite only playing over 100 games in one of those seasons. He hit 36 homers, 182 RBI’s, appeared in two All-Star games, won a Gold Glove in 2010 and appeared in the 2010 and 2012 ALDS.

Encarnacion lasted seven more seasons in Toronto compared to Rolen’s three in Cincinnati, and thus Edwin accumulated a WAR of 24.3 to Rolen’s 7.6. Not only did Encarnacion provide the Jays with longevity and production, during those final three years on Rolen’s contract, as they paid Encarnacion just over half of what Rolen received, according to Baseball Reference.

Edwin has since moved on to Cleveland where he appeared in two postseasons and was traded this offseason once again to the Seattle Mariners. With just a year left on his contract, he will remain a trade possibility as the year goes on.

The Hall of Fame class of 2019 was announced on Tuesday night and Scott Rolen was able to compile 17.2 percent of the votes in his second year on the ballot, leaving him eight years to hit the 75 percent of votes needed.

Jays Journal Contributor: Cam Black-Araujo

ATLANTA, GA – MAY 17: Jose Bautista #19 of the Toronto Blue Jays warms up before the game against the Atlanta Braves at SunTrust Park on May 17, 2017 in Atlanta, Georgia. (Photo by Scott Cunningham/Getty Images)
ATLANTA, GA – MAY 17: Jose Bautista #19 of the Toronto Blue Jays warms up before the game against the Atlanta Braves at SunTrust Park on May 17, 2017 in Atlanta, Georgia. (Photo by Scott Cunningham/Getty Images) /

August 21st, 2008- Blue Jays Obtained Jose Bautista From The Pirates In Exchange For Robinzon Diaz

On August 21, 2008, the Blue Jays and the Pittsburgh Pirates made an extremely minor trade. The Pirates sent the recently optioned Jose Bautista, while the Blue Jays traded a player to be named later, who eventually was Robinzon Diaz.

Initially, the trade was shrugged off as an unimportant, pedestrian deal that was made out of pity for both players. Bautista had bounced around and Diaz seemed to be itching for a chance at some big league time. No one could’ve imagined this immense impact this deal had on the future of the franchise.

Diaz would end up appearing in 43 games over the next two seasons, while Bautista would go on to mash 277 home runs for the Blue Jays over the next eight years. Currently sitting fifth among active players in home runs, Bautista, now 38, was named an All-Star in five consecutive seasons (2010-2015) and slashed an outstanding .268/.390/.555 over that span. He also won three Silver Slugger Awards in 2010, 2011 and 2014.

A true franchise icon, Bautista racked up 288 homers (second in franchise history), 766 RBI (third), 219 doubles (seventh), 803 walks (second), 1103 hits (sixth), 49 intentional walks (third), 790 runs (second), and 56 stolen bases (23rd) in 1235 games with the Blue Jays.

It is impossible to overstate the importance of Jose Bautista’s influence on Blue Jays baseball. From the iconic bat flip to the abundant amount of awe-inspiring throws from the outfield, Bautista became a staple of Toronto baseball in the 21st century.

Since leaving Toronto, Bautista has logged 122 games for the Braves, Mets, and Phillies, slashing .203/.348/.378 in 399 plate appearances. Having previously played for the Royals, Rays, and Orioles, he is currently 40th among active players in WAR (35.6) and second among active right-fielders in JAWS. Though he likely won’t be back in a Blue Jays uniform anytime soon, fans will always have a special place in their heart for the one they call “Joey Bats”. A near lock to be immortalized on the Level of Excellence, Jose Bautista will always be a Blue Jays legend.

Jays Journal Contributor: Hayden Godfrey

TORONTO, ON – OCTOBER 04: Former Major League Baseball player Roberto Alomar throws out the ceremonial first pitch prior to the American League Wild Card game between the Toronto Blue Jays and the Baltimore Orioles at Rogers Centre on October 4, 2016 in Toronto, Canada. (Photo by Vaughn Ridley/Getty Images)
TORONTO, ON – OCTOBER 04: Former Major League Baseball player Roberto Alomar throws out the ceremonial first pitch prior to the American League Wild Card game between the Toronto Blue Jays and the Baltimore Orioles at Rogers Centre on October 4, 2016 in Toronto, Canada. (Photo by Vaughn Ridley/Getty Images) /

December 05th,1990- Blue Jays Traded Tony Fernandez and Fred McGriff To The Padres For Roberto Alomar And Joe Carter

Imagine turning on the news to find out two iconic players who have been instrumental in helping build the Blue Jays as a strong competitive team had just been traded. This is what happened on December 5, 1990.

The Blue Jays coming just two wins shy of a playoff spot in 1990 had to shake things up a little. Roberto Alomar was a young fresh face on the scene and just finished competing in 1990 All-Star game and Joe Carter who previously averaged 25 or better home runs was about to pack their bags and head North of the Border.

No one could have predicted how successful this trade was going to be for the Blue Jays, let’s face it, San Diego did not come out poorly on this. Fred McGriff was always a home run threat and Tony Fernandez was a fantastic defensive shortstop that any team would welcome.  In 1991, the Blue Jays finished 1st in the AL East standings and returning to the postseason and coming just short of their first World Series appearance. This move led the Jays to make key additions the following year including adding Dave Winfield who won a Silver Slugger and came in 5th place in the MVP standings for the Blue Jays.

Joe Carter would go on to become a national hero with the home run that was heard around the world. Carter’s dedication to the game, the city made him one of the most likeable players to ever wear a Blue Jays jersey. His consistency at the plate and hard work was always a comfort for Cito Gaston to rely on.

Roberto Alomar, well, what can be said about his time with the Blue Jays. Alomar has set the bar high for what is expected of a second baseman. Over his career he appeared in 12 all-star games, 10 Gold Gloves (five of which he achieved with the Blue Jays from 1991 – 1995) and usually in the top ten in votes for the league MVP during his time with Toronto. Alomar also achieved the 1992 ALCS MVP.

In the end, Roberto Alomar and Joe Carter were the key ingredients the Blue Jays needed to not only make the postseason but bring the Blue Jays their only World Series Championships back to back in 1992 and 1993.

Jays Journal Contributor: Marc Tremblay

NEW YORK – AUGUST 03: Vernon Wells #10 of the Toronto Blue Jays bats against of the New York Yankees on August 3, 2010 at Yankee Stadium in the Bronx borough of New York City. The Jays defeated the Yankees 8-2. (Photo by Jim McIsaac/Getty Images)
NEW YORK – AUGUST 03: Vernon Wells #10 of the Toronto Blue Jays bats against of the New York Yankees on August 3, 2010 at Yankee Stadium in the Bronx borough of New York City. The Jays defeated the Yankees 8-2. (Photo by Jim McIsaac/Getty Images) /

January 21st, 2011- Blue Jays trade Vernon Wells To The Angels For Mike Napoli and Juan Rivera

The Vernon Wells trade wasn’t as much about the players being exchanged then it was about the financial flexibility it created for the Blue Jays. Alex Anthopoulos did the impossible shipping Wells and his enormous contract to the Los Angeles Angels. The deal at the time rocked the baseball world as many thought the contract was unmoveable and the Blue Jays would be saddled with the financial repercussions until the term expired.

Following a career year in 2006, Wells signed a 7 year/ $126 million dollar contract extension with the Blue Jays. Wells would eventually regress and the contract would handcuff the Blue Jays front office from making future moves. Anthopoulos recently went on record to say they may not have been able to keep Jose Bautista in the fold had they not packaged Wells and the remaining $86 million owed to the Angels for Mike Napoli and Juan Rivera.

Wells would play for only three more seasons following the trade and accumulate a -0.3 WAR rating with the Angels and Yankees. Prior to the trade, Wells totaled a 28.7 WAR in his 12 years with Toronto.

The Jays would flip Napoli almost immediately to the Texas Rangers in exchange for reliever Frank Francisco and Rivera would be designated for assignment later that the season after 70 games with the club.

This trade along with the Josh Donaldson acquisition have to be the two most memorable and lopsided trades of the “Silent Assasin’s” tenure with the Blue Jays. Well done A.A.

Jays Journal Site Expert: Clayton Richer

23 Feb 1997: Pitcher Juan Guzman of the Toronto Blue Jays looks on during spring training in Dunedin, Florida. Mandatory Credit: Andy Lyons /Allsport
23 Feb 1997: Pitcher Juan Guzman of the Toronto Blue Jays looks on during spring training in Dunedin, Florida. Mandatory Credit: Andy Lyons /Allsport /

September 22md, 1987- Blue Jays Acquired Juan Guzman From The Dodgers For Mike Sharperson

A lot of things went right to put together the championship teams of 1992 and 1993, and one of the more underrated pieces of the puzzle happened in 1987. The Blue Jays made a late-season deal with the Dodgers and sent Mike Sharperson to L.A. in exchange for a young pitcher in High-A by the name of Juan Guzman.

Guzman wouldn’t reach the big leagues until 1991, but once he arrived as a 23-year-old he was dominant right out of the gate. He made 23 starts in his debut season in 1991 and finished second in Rookie of the Year voting. The pressure of pitching for a contender didn’t seem to bother him one bit, as he finished the season with a 10-3 record, a 2.99 ERA and a WHIP of 1.183. He followed that up with another dominant season in 1992, going 16-5 with a 2.64 ERA and earning an All-Star appearance. He was solid again in 1993 as well despite having a little higher numbers.

The playoffs were perhaps the most important contribution of Guzman’s Blue Jay career, as he made eight starts from 1991-93 and went 5-1 with a 2.44 ERA while earning two World Series rings. He impressive in nearly every outing, but I’ll personally never forget his start against the Atlanta Braves in 1992 when he went eight innings, striking out seven and allowing just one earned run.

He had some ups and downs in a Blue Jay uniform from 1994-98, and was eventually traded to Baltimore in ’98, and also made stops in Cincinnati and Tampa Bay before retiring in 2001. It was a bit of a shame that his career was over at just 33 years old, but there’s no denying the crucial impact he made for those championship Blue Jays teams.

Next. Blue Jays: Worst trades in franchise history. dark

As for the return? Sharperson was Toronto’s first-round pick back in 1981 and was taken 11th overall, but he never developed into the star that the Jays or the Dodgers hoped he would be. He did have a couple of good seasons in L.A. in 1991 and 1992 which even included an All-Star appearance (’92), but he struggled the following year, and only played in seven more MLB games after that season.

Jays Journal Site Expert: Chris Henderson

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