The Trade That Never Was


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As Dave Dombrowski and the Red Sox embark on the 2016-17 MLB Offseason, I’ve decided to revisit a trade that almost came to fruition nine years ago.

Many Sox fans may or may not know that the Red Sox nearly acquired two-time Cy Young Award Winner Johan Santana from the Minnesota Twins after winning the 2007 World Series. Following the aforementioned 2007 season, the Red Sox looked primed to contend for another title in the subsequent year; however, General Manager Theo Epstein still felt the need to bolster a pitching staff that featured 20-game winner Josh Beckett, Japanese phenom Daisuke Matsuzaka, and talented youngsters Jon Lester and Clay Buchholz.

The Minnesota Twins were in an interesting situation as they were one of the better teams in baseball, but they could not afford to keep Santana along with stars Joe Mauer and Justin Morneau. Since Santana was such a sought-after commodity, the Twins’ asking price was astronomical, and the Red Sox came to the table with a more-than-fair offer.

According to, the Red Sox offered the Twins a hefty package including; Jon Lester, Justin Masterson, Jed Lowrie, and Coco Crisp. While the offer was competitive, the Twins were reluctant to trade their ace in a deal that did not feature centerfielder Jacoby Ellsbury who made waves during the 2007 Postseason. The Red Sox were firm on their position to not include Jacoby Ellsbury in a trade that also featured Jon Lester or Clay Buchholz, so a deal never came to fruition.

On February 2, 2008 Santana was eventually dealt to the New York Mets in exchange for Carlos Gomez, Phillip Humber, Deolis Guerra, and Kevin Mulvey. To relate this package to that of the Red Sox, Gomez was the “Ellsbury” and Humber was the “Lester” or “Buchholz”, and the other guys were both pitchers who never did anything in the MLB.

Looking back, the Red Sox unequivocally made the right decision by not overextending themselves for Santana who subsequently signed a seven year deal worth $137.5 million extension with New York. In his first season with a different team, Santana was stellar in 2008 finishing third in the NL Cy Young Award and continued to pitch well in the following two seasons even though he did not pitch as many innings or was as dominant. Then the 2011 season came along with the premature demise of a possible Hall of Fame pitcher. Santana missed the entire 2011 season due to shoulder surgery and pitched in the final campaign of his career in 2012 where he notably threw a 134 pitch no-hitter.

Unfortunately, Johan Santana has not pitched in the Major Leagues since that year, while Lester went on to have a breakout season in 2008 matching Santana with 16 wins to go along with a 3.21 ERA. Lester has since gone on to become one of the best lefties in the game leading the Red Sox to another World Series in 2013. Ellsbury, whom the Red Sox were unwilling to deal, became an All-Star caliber player also contributing to the 2013 squad.

Masterson and Lowrie were both dealt in following years in separate trades for Victor Martinez and Mark Melancon respectively; both players had periods of success in their tenures in the MLB. Last, but not least, is Coco Crisp who was the veteran in the trade who would have been the piece to fill the hole in the Twins outfield. Crisp is still contributing in baseball almost helping the Cleveland Indians win the World Series in 2016.

As for the deal that did happen, Gomez was the only difference-maker, while Humber made a name for himself with a perfect game while on the White Sox, he has ultimately been a bust. I bet former Twins GM Bill Smith will not be happy reading this as Lester alone would have made the deal worth it, not to mention Lowrie, Masterson, and Crisp. Overall, the Red Sox dodged a bullet, and maybe this is a good deal to reference as the Sox look to add elite pitchers like Chris Sale and Jose Quintana.

by Joe Spinosa