Jon Lester

The 5 Most Impactful Red Sox Trade Deadlines Since 2000

Barring some crazy blockbuster (Chris Sale, maybe?), the Red Sox are in for a quiet trade deadline Monday. That’s not because the Sox can not or should not make moves. They’ve already added to their bench, bullpen and starting rotation. More deals are unlikely, and probably unnecessary, unless a savior is joining the rotation.

A quiet day would be an abnormal development for the Red Sox, who are usually active at the deadline, especially since the turn of the century as they’ve consistently made major moves to either boost a playoff-caliber team, or tear apart the bad ones. Many deals succeeded, leading to championship runs. Some failed miserably. Others, well, didn’t do much of anything. Regardless, Theo Epstein, Ben Cherington and Co. were never afraid to pull the trigger.

Today’s trade deadline may leave Red Sox fans underwhelmed, but many deadlines haven’t. Let’s look back at some of those busier deadlines and see just how well (or poorly) they turned out. I present you with the five biggest Red Sox trade deadlines of the 21st century.

5.) 2013

Red Sox acquire right-handers Jake Peavy and Brayan Villarreal, send shortstop Jose Iglesias to the Tigers and send right-handers J.B. Wendelken and Francelis Montas to the White Sox

This trade technically came the day before the 2013 trade deadline, but I make the rules here, and I say that’s good enough to make this list. Anyway, the 2013 Red Sox were in the midst of a worst-to-first turnaround, but needed another starting pitcher for their playoff push. Insert Jake Peavy. The righty gave the Sox just what they needed, posting a 3.82 FIP in 10 regular-season starts and helping them win the World Series. Peavy’s 2013 postseason was less than stellar, but he did start the ALDS clincher against the Rays, allowing just one run on five hits over 5.2 innings. The Red Sox got an ok half season out of Peavy in 2014 before shipping him to the eventual world champion Giants in 2014.

The only notable loss for the Red Sox in that deal was Jose Iglesias, but even his departure wasn’t a major letdown at the time with Stephen Drew and Dustin Pedroia at shortstop and second base, respectively, Will Middlebrooks (sort of) contributing at third and Xander Bogaerts on his way. Iglesias was known primarily for his glove coming through the Sox organization, but was hitting well early on in 2013, posting a .285 TAv in 63 games before being dealt. Iglesias missed all of 2014, owned a .252 TAv in 2015 and has a .243 TAv this season. Meanwhile, Bogaerts could be the one of the best offensive shortstops in the majors for years to come. Safe to say the Red Sox made the right move.

Iglesias still contributed to the 2013 title, by the way.

That led to this:

4.) 2009

Red Sox acquire catcher Victor Martinez from the Indians for right-hander Justin Masterson, left-hander Nick Hagadone and catcher Bryan Price

The playoff-bound Red Sox bolstered their lineup with one big swap, adding Victor Martinez in exchange for Justin Masterson and a pair of prospects. Martinez proved to be a nice addition, as he split time between catcher and first base over 183 regular-season games between 2009 and 2010. Martinez posted a .302 TAv in 237 plate appearances in 2009 and a .281 mark the next year. He didn’t give the Red Sox the postseason production they were hoping for in 2009, collecting just a pair of hits, but that run also lasted just three games.

This trade wasn’t necessarily a win or loss for either team, but it’s safe to say the Indians got more out of the deal. Masterson pitched five solid years in Cleveland, his best being in 2013 when he was the ace of the staff and led the Indians to a postseason berth with a 2.63 DRA and 3.38 FIP. The righty’s career has since flamed out after a disastrous season with the Red Sox in 2015, but the Indians certainly got the best of him.

3.) 2014

Red Sox trade left-hander Jon Lester to the A’s for Yoenis Cespedes and a competitive balance pick; send right-hander John Lackey and left-hander Corey Littrell to the Cardinals for outfielder Allen Craig and right-hander Joe Kelly; trade left-hander Andrew Miller to the Orioles for right-hander Eduardo Rodriguez and send shortstop Stephen Drew to the Yankees for utility infielder Kelly Johnson

Making one major trade at the deadline is big. Two deals is impressive. Four deals in one day is on another level. That’s exactly what the Red Sox did at the 2014 trade deadline as they shipped off a number of veterans over four trades, eyeing the future in the midst of a last-place season.

The Sox’s deadline activity actually began five days earlier when they traded Peavy to the Giants for Heath Hembree and Edwin Escobar. Escobar is no longer with the team, but Hembree has turned into a nice innings eater out of the bullpen. The real fireworks, however, began early on the morning of the deadline when Jon Lester was sent to the A’s for Yoenis Cespedes. Lester was once again pitching like a top-of-the-rotation starter, but the Sox were out of contention and the lefty was in the final year of his contract with no long-term agreement in sight. Cespedes, meanwhile, was a big bat with another year left on his deal. Lester picked up where he left off upon joining the A’s, posting a 2.35 ERA and 3.16 FIP over 11 starts. The Sox pursued Lester in the offseason, but lost out to the Cubs. Cespedes owned a .269 TAv over 213 plate appearances before being dealt to Detroit for Rick Porcello in the offseason. Sure, Porcello doesn’t seem like a stellar return for Lester (although Porcello has been one of their two most dependable starters this season), but they also could have lost the lefty for nothing that offseason had they not traded him.

Then there was the deal we’d all like to forget. That was the deal that brought Allen Craig and Joe Kelly to Boston in exchange for John Lackey. The trade made plenty of sense at the time. Lackey was pitching well, but had little future left in Boston, especially after expressing his displeasure about pitching at the major-league minimum in 2015. Craig was a former All-Star who appeared to be simply having a bad year, while Kelly was young, could throw hard and had shown potential after posting a 2.69 ERA over 15 starts in 2013. Two years later, the deal looks as bad as ever for the Red Sox. Lackey posted a 2.77 ERA while pitching at the minimum for the Cardinals last season. Craig spent most of last season in Triple-A and has since fallen off the face of the earth. Kelly has spent his time with the Red Sox either hurt, or bouncing between Triple-A and the majors.

As dominant as Andrew Miller has been over the last two-plus years, a young pitcher like Eduardo Rodriguez was about the best you were going to get for a rental reliever (how times have changed). The Orioles got the most out of Miller, who owned a 1.16 FIP in 23 appearances with Baltimore in 2014. He’s since become one of the best closers in baseball over the past two seasons. The Red Sox, meanwhile, got a potential middle-of-the-rotation arm for a player they would probably lose to free agency anyway.

The Stephen Drew trade proved to be insignificant. He gave the Yankees an ok season and a half and Kelly Johnson gave the Red Sox next to nothing. However, the trade opened up shortstop for Bogaerts, and we all know how that’s gone.

This deadline was as crazy as it gets for any team. At the time, the Red Sox seemingly won the day, but hindsight shows that not all of it worked out as planned. The Lackey deal is a perfect example of that. However, it would’ve looked worse if the Red Sox lost some of these players to free agency.

2.) 2008

Red Sox acquire outfielder Jason Bay from the Pirates, trade outfielder Manny Ramirez to the Dodgers and send right-hander Craig Hansen and outfielder Brandon Moss to the Pirates

This trade was years in the making. It was far from the first time Manny Ramirez had been part of a trade rumor, and even further from the first time he wanted out of Boston. In 2008, the Red Sox finally pulled the trigger, and got a player in Jason Bay who could fill Ramirez’s void immediately. From a straight trade standpoint, the Red Sox and Dodgers both got solid production for a year and a half of service. Bay posted a .308 TAv in 211 plate appearances with the Sox in 2008, while owning a .302 mark the next season. Ramirez was even more impressive with his .425 TAv in 229 plate appearances with the Dodgers in 2008 and .336 mark in 2009 as LA reached the NLCS both seasons. Ramirez was clearly better than Bay during that time, but by that point he had been nothing but a distraction in Boston and needed to go.

As for the prospects the Red Sox gave up. Craig Hansen’s career continued to be forgettable. Brandon Moss’ career never really materialized until his 2012 arrival in Oakland in 2012, where he totaled 76 home runs over three seasons. Moss, 32, has a .323 TAv and 17 home runs for the Cardinals this season.

1.) 2004

Red Sox acquire shortstop Orlando Cabrera from the Expos and first baseman Doug Mientkiewicz from the Twins, and send shortstop Nomar Garciaparra and outfielder Matt Murton to the Cubs, and acquire outfielder Dave Roberts from the Dodgers for outfielder Henri Stanley

This may go down as the biggest trade deadline in Red Sox history. It was significant enough that they traded, at the time, one of the most iconic players in team history. Add in the fact that it helped propel the Sox to their first World Series title in 86 years and you’re talking about a deadline worth telling your grandkids about.

We start, of course, with the Nomar Garciaparra trade. Garciaparra had been the face of the Red Sox since his 6.0 WARP rookie season in 1997 and a clear fan favorite. He was also really, really good, owning a 43.7 WARP between 1997 and 2003 (keep in mind he missed most of 2001). But by July 2004, he had seemingly overstayed his welcome in Boston. He was in a contract year with no promise of returning, had become a defensive liability and was expected to miss more time with an Achilles injury. Epstein, in a stroke of groinal fortitude, dealt away the superstar in hopes of shoring up the team’s “fatal flaw”: defense.

Epstein got just what he was looking for from Orlando Cabrera. The shortstop’s .268 TAv with the Red Sox was comparable to Garciaparra’s .272 TAv with the Sox in 2004, but he also posted a positive FRAA and played 15 more games than Garciaparra did in the final two months. Cabrera left at the end of the season and the Red Sox began a carousel at shortstop over the next decade, but the championship and Garciaparra’s rapid decline soon after was enough to justify the move.

The Dave Roberts trade was a footnote in the midst of an active deadline, and with good reason. The outfielder made just 101 plate appearances and posted a .251 TAv. He was simply acquired to add speed, defense and depth off the bench. However, Roberts is also responsible for the biggest stolen base in Red Sox history.


It’s unlikely the Red Sox will do anything to top these trade deadlines this season. But that’s why a list like this exists. You don’t get fireworks every season. When you consider the moves the Sox have made in the past month, it makes even more sense for this deadline to be a quiet one. That’s not always a bad thing.

 Photo by USA Today Sports Images

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1 comment on “The 5 Most Impactful Red Sox Trade Deadlines Since 2000”

Awesome trip down memory lane …great piece and insight on the deals. If I may add, it also makes sense to be quiet when sometimes it’s actually the moves a team doesn’t make that are best. For example, not trading Betts or JBJ for pitching in 14 or ’15 (or even this year), similarly with Lester and Ellsbury (for Santana) in ’07. If Moncada and Benintendi are even close to as advertised, Sox fans will be glad they weren’t traded.

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