Flashback Friday: The Edwin Encarnacion/Scott Rolen Trade

Looking back, it’s incredible to think about the circumstances in which two of the most prolific hitters in Blue Jays history came to Toronto. Jose Bautista’s story is a tale in itself, but this time it’s Edwin Encarnacion’s turn.

This week’s Flashback Friday focuses on the trade from 2009 that send Scott Rolen to the Cincinnati Reds for none other than Edwin Encarnacion among others.

Heading into the 2009 trade deadline, the Blue Jays were 49-54 and a full 13 games back of the division-leading New York Yankees. Although Toronto started off the season strong, close to the end of July, the essentially waved the white flag.


In 2009, the Blue Jays traded several of their cornerstone franchise players; Alex Rios, Roy Halladay, and on July 31st, their third baseman, Scott Rolen. During the 2007 offseason, he requested a trade out of St. Louis and Toronto provided him a safe haven.

His 2008 season with the Blue Jays was met with mixed results, but Rolen proceeded to put up incredible numbers the following year; Scott Rolen owned a slash line of .320/.370/.476. And with another year on his contract, Rolen suddenly looked very good to prospective teams in the playoff race.

So as the Blue Jays began to come with grips that 2009 would not be their year to contend, they started to listen on offers on their best players; one of the main ones being Scott Rolen. It was also revealed that he approached management and requested a trade to be closer to home in Indiana.

Considering how well Rolen was playing and that he essentially forced J.P. Ricciardi’s hand, I’d say the Blue Jays got a pretty decent haul in return.

And while some were left sobbing playing “Viva La Vida” on repeat for hours on end, Scott Rolen’s departure would open up an opportunity for one of the players on their way coming back to Toronto.

The full trade was Scott Rolen for third baseman Edwin Encarnacion and pitchers Josh Roenicke and Zach Stewart. The Blue Jays also kicked in another $4 million dollars for the Reds, which was essentially the remainder of Rolen’s 2009 salary.

The trade was somewhat curious by the Reds because they were in a similar position in the standings as the Blue Jays; fourth place in the NL Central and 10 games back of the St. Louis Cardinals for the division lead.

At the time, Edwin Encarnacion was a maligned third baseman, but pitching prospects Zach Stewart and Josh Roenicke were viewed as the real steals of the trade from the Reds.


Stewart projected to be a starter while Josh Roenicke was looked upon as a potential late relief arm or closer of the future. Edwin Encarnacion was the forgotten man in the deal.

For the Reds, the acquisition of Scott Rolen was a clear upgrade at third base for them both offensively and defensively. Encarnacion struggled mightily at the hot corner that season with 73 errors in his first full four seasons in Cincinnati.

The Reds had signed Edwin to a two-year/$7.6 million dollar contract to buy out his first two years of arbitration, and after the results of his 2008 and 2009 campaign, they were more than happy to dump the remainder of the contract on the Blue Jays.

Because Edwin Encarnacion hit 26 home runs during his 2008 campaign, I think the Reds (and to some extent the Blue Jays as well) overlooked his defensive shortcomings for his potential to hit the ball out of the ballpark.

Encarnacion projected to be a power bat by posting 15 or more home runs from 2006-2008, but he was clearly a liability at third base; perhaps that’s the main reason the Reds opted to go with the slick-fielding Rolen at third base instead.


In retrospect, the trade was a clear win for the Blue Jays as Edwin Encarnacion eventually developed into one of the best power hitters in all of baseball, but that was before he was designated for assignment by the Blue Jays following the 2010 season.

The Oakland A’s acquired Encarnacion shortly thereafter, but they also jettisoned him and the Blue Jays wisely brought him back on a one-year deal with an option.

The Reds also made out fairly well in the trade, considering the following year, Cincinnati captured the NL Central title. But even then, the trade was viewed as a win for the Reds because they still had the best player in the deal: Scott Rolen.

Josh Roenicke was immediately put into middle relief with the Blue Jays and it was met with mixed results the following season as well. He was eventually let go by Toronto, but enjoyed some brief success with the Colorado Rockies.

Zach Stewart was touted as a blue chip prospect, and in 2009 he rocketed through the ranks by starting the season in Single A and eventually finishing his campaign in Triple A with the Las Vegas 51’s.

Stewart was called up to the Blue Jays in 2010 but struggled at the Major League level. At the 2010 deadline, he was involved in the three team trade which saw him shipped to the Chicago White Sox and Colby Rasmus came to the Blue Jays.

Judging by how dominant Edwin Encarnacion has been these past few years, you’d think he was the type of player that was drafted and developed to be born into a star like Bryce Harper or Mike Trout. But Edwin’s path to stardom was not a linear path.

Encarnacion was essentially a throw-in player of the Scott Rolen trade and a salary dump by the Cincinnati Reds. And after a couple of chances with the Blue Jays, he’s become one of their most feared hitters in recent memory.

Not too bad for a guy who was cast aside by not one, not two, but three organizations.

Ian Hunter

Ian has been writing about the Toronto Blue Jays since 2007. He enjoyed the tail-end of the Roy Halladay era and vividly remembers the Alex Rodriguez "mine" incident. He'll also retell the story of Game 5 of the 2015 ALDS to his kids for the next 20 years.

2 thoughts on “Flashback Friday: The Edwin Encarnacion/Scott Rolen Trade

  • August 15, 2014 at 3:36 pm

    I'm starting to think that trades like this are what the new Red Sox model is all about, and why they are trading for guys like Allen Craig rather than prospects.

  • August 15, 2014 at 7:53 pm

    He never did the Edwing in Cincinnati XD

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