What if Boston Red Sox played 2014-15 offseason differently?

The 2014-15 offseason had many big names, and the Boston Red Sox made some big mistakes. What if it had gone differently?

The Boston Red Sox are well known for their free agent mistakes. Carl Crawford, David Price, Julio Lugo, and John Lackey were all handed big contracts only to disappoint during their time in Boston. However, none of those signings were absolute disasters.

While Zack Greinke turned out to be the better option for the 2015-16 offseason, Price did have his moments in Boston. He made a few key starts to lead the Red Sox to a World Series title, and won the AL Comeback Player of the Year in 2018. Besides, the Red Sox avoided something far worse by passing on Johnny Cueto and Jordan Zimmerman.

Crawford will forever be remembered in Boston for the wrong reasons. But the Red Sox needed an outfielder, and the next best option was Jayson Werth — who was entering his age 32 season and didn’t exactly live up to his contract either. He didn’t hurt the team much anyway, as the Red Sox were able to ship Crawford away to Los Angeles before he did any real damage.

Lugo was a serviceable player who the Red Sox managed to trade away, and Lackey was able to turn it around towards the end of his contract and was a major part of the 2013 championship team.

The point is, almost no free agent deal is purely a disaster. A worse alternative or some sort of silver lining usually comes with even the biggest catastrophes. However, Boston’s decisions during the 2014-15 offseason proved to be an exception.

It’s hard to say how they messed up so badly. Perhaps it was partially due to the major successes from 2004 to 2010. Those made the Red Sox one of the biggest franchises in sports and caused the failures of the new decade to be so humiliating. So maybe ownership got a little gun-shy. Maybe there was some bad luck mixed in too. No one could have foreseen this epic collapse from two players that were previously seen as the faces of their franchise. The Red Sox needed a third baseman and a left fielder, and so they went out and got the two biggest names on the market.

Pablo Sandoval and Hanley Ramirez cost the Red Sox $41 million dollars per year and combined for a negative bWAR during their time in Boston. But the Red Sox were still able to succeed despite the presence of these players. They won three consecutive AL East titles, the third of which ended with a World Series parade.

The part where the Sandoval and Ramirez deals hurt the most is who they could have signed instead. The Red Sox badly needed starting pitching at that time, and Max Scherzer had just hit the free agent market. The Tigers ace had already established himself as one of the best pitchers in baseball, winning the Cy Young award in 2013 and finishing fifth in 2014.

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Instead, the Red Sox opted to go with a rotation consisting of Joe Kelly, Clay Buchholz, Justin Masterson, Wade Miley, and Rick Porcello, resulting in those infamous “He’s the Ace” shirts. Scherzer would go on to sign a deal with the Washington Nationals for seven years and $191.4 million. He has finished fifth in the Cy Young Award voting in all five seasons with the Nationals so far, and even won the award in back-to-back seasons(2016 and 2017).

Hindsight is 20/20, but while we’re looking back at how this offseason could have gone, let’s try to fill the holes at third base and outfield too. Infielder Asdrubal Cabrera signed a deal that totaled three years and $25 million, and averaged .275 with 17 home runs per season over the course of his contract.

Nelson Cruz would not have been able to play in the outfield forever, but after signing a four year, $57 million dollar deal with the Mariners, he received MVP votes in three separate seasons in Seattle.

If Boston had signed Scherzer, they would have no longer needed to go after Masterson. In the end, Scherzer, Cruz, and Cabrera would have cost less per year than Ramirez, Sandoval, and Masterson did.

The Red Sox were able to figure it out anyway, and have been one of the most successful franchises in the MLB in recent years. Regardless, the 2014-15 offseason will go down as one of the absolute worst in Red Sox history.