Boston Red Sox: Remembering the best trades in franchise history

Any team that’s been around as long as the Red Sox has made countless trades, some good and some bad. In this article we’ll take a look at some of the best deals they’ve made.

Even though the Boston Red Sox have produced countless good to great homegrown players throughout their long and storied history, many of their best players were acquired via trade. Like any team that’s been around as long as they have, the Sox have made their share of bad trades. However, they’ve also hit on a lot and some of those acquisitions turned into Red Sox legends.

The following is a list of some of the greatest trades in Red Sox history. Some of these players were only on the team for a short time but made a big impact, others spent the majority of their careers in Boston and in the process became all-time heroes.

In many cases, the Red Sox gave up players who ended up being very good for the teams on the receiving end while other times they gave up little of value and swindled their trade partners. Here’s a list of the best trades the Red Sox have made in their history.

In no particular order, let’s begin.

Dennis Eckersley

Before he was one of the greatest closers of all time for the Oakland A’s, before he became well-known on Red Sox NESN broadcasts for “cheese” and “moss” and “going bridge,” Dennis Eckersley was a really good starting pitcher.

After spending the first three seasons of his career in Cleveland, he was traded to the Red Sox in 1978 for Rick Wise, Ted Cox, Mike Paxton, and Bo Diaz. The impetus of the trade was a bit strange as Cleveland shipped Eck out because there was clubhouse drama when his first wife cheated on him with his Indians teammate Rick Manning!

Eck immediately paid dividends for the Sox by going 20-8 in 1978 with a 2.99 ERA and 162 strikeouts. He had another great season in 1979 when he went 17-10 with a 2.99 ERA and 150 strikeouts, but he struggled the rest of his time in Boston.

From 1980 to 1984 Eck saw his velocity diminish and he’d go 47-52 during those years. Upon being traded to the Chicago Cubs midway through the 1984 season, Eck finished his Red Sox career with an 84-71 record, a 4.13 ERA, and 771 strikeouts.

After leaving the Red Sox, Eckersley struggled in Chicago before kicking his alcoholism and turning into one of the game’s greatest closers as an Oakland A in the late 1980s and 1990s. He returned to Boston for the final season of his career in 1998 as a set-up man.

While he wasn’t the greatest pitcher the Red Sox ever had, he was a crucial contributor to the 1978 team that should have went to the World Series and was much better for the Red Sox than the guys they sent to Cleveland. And of course, we all know what he’s like as a broadcaster (just don’t ask David Price).

Jason Varitek and Derek Lowe

This one is a twofer and might be one of the biggest swindles the Red Sox have ever pulled off in their 100-plus year history. In one fell swoop they sent out a decent reliever and received two players who were instrumental in helping them end eighty-four years of futility and finally win the World Series.

Heathcliff Slocumb was a pretty good reliever for the Red Sox, saving 31 games in 1996 and 17 in 1997 when he was traded to the Seattle Mariners for Jason Varitek and Derek Lowe. Seattle was desperate for relief pitching as they made their postseason push and parted with their two players.

Lowe had only appeared in twelve career games and Varitek was still in the minor leagues when they arrived in Boston. While Slocumb did help Seattle make the postseason in 1997 before his career fizzled out (he was out of baseball by 2000), Varitek and Lowe became cornerstones of the 2004 World Series champions.

Lowe spent his eight seasons in Boston in the same way as Tim Wakefield, bouncing between the rotation and the bullpen. He won 21 games as a starter in 2002 and 17 the following year. For his Red Sox career (1997-2004), he compiled a 70-55 record (111 starts in 384 appearances) with 85 saves, a 3.57 ERA, and 673 strikeouts.

For good measure, Lowe was the winner in all three clinching games in 2004: Game Three of the ALDS, Game Seven of the ALCS, and Game Four of the World Series. He left after the season in free agency with his Red Sox legacy secure.

As for Varitek, he became the Red Sox regular catcher in 1998 and spent his entire career in Boston before retiring after the 2011 season. He was the team captain from 2005-2011 and helped them win the World Series in 2004 and 2007. He put up a career .256 batting average to go along with 193 home runs and 757 RBI. He also caught four no-hitters, which is a league record.

This trade is often pointed to as being one of the most lopsided not just in Mariners history, but in baseball history. It’s hard not to argue that it’s also one of the best in Red Sox history.

Pedro Martinez

Pedro Martinez has already been included in my lists of most important players in Red Sox history and best Red Sox players of the 1990s. There’s no need to belabor the point when it comes to discussing his greatness while he was in Boston, seven glorious years when he was one of the most dominating pitchers in all of baseball.

This one is up there with the Varitek/Lowe trade as one of the best in Sox history. After the 1997 season, then-GM Dan Duquette traded Carl Pavano and Tony Armas Jr. to the Montreal Expos for Pedro, who was heading to free agency. Duquette then signed Martinez to a seven-year extension worth $92 million which at the time was the most ever for a pitcher.

I’ve written about Pedro’s numbers before (check out those previous list articles) so there’s no need to go through them again here. Suffice it to say that the two Cy Young Awards, four postseason appearances, and World Series he helped them win are testament enough. Mark this deal as one of the best in Red Sox history.

Curt Schilling

The deal for Curt Schilling might be one of the best and also the most important that the Red Sox have ever made. There are numerous reasons why the 2004 Red Sox were able to finally end the eighty-six year drought and win the World Series and Schilling is chief among them.

In my article on the worst trades in Red Sox history, I included the deal that sent Schilling to Baltimore when he was a prospect in 1988. Luckily, in 2004 they got a do-over and made it right. After winning the World Series (and co-World Series MVP award) with the Arizona Diamondbacks in 2001, Schilling was traded to the Red Sox in the winter of 2003 for Jorge de la Rosa, Casey Fossum, Brandon Lyon, and Mike Goss.

All ended up being forgettable while Schilling would help the Red Sox win the World Series in 2004 and 2007. In 2004, the big righty went 21-6 with a 3.25 ERA and 203 strikeouts. He was even better in the postseason and forever entered Red Sox lore when he pitched on a hastily surgically repaired ankle with a “bloody sock” in both Game Six of the ALCS and Game Two of the World Series, winning both decisions.

In the four seasons in Boston that wrapped up Schilling’s career, he went 53-29 with a 4.20 ERA and 574 strikeouts. He was never the same after 2004 and relied more on his guile and command once his velocity diminished. He was instrumental in winning another World Series in 2007 before finally retiring.

The Red Sox were able to bring Schilling full circle so that he could end his career where it started in what was one of the biggest trade heists in franchise history.

Josh Beckett and Mike Lowell

The final result of this trade ended up being better than the initial reaction to it. When then-Chief Baseball Officer Theo Epstein sent Hanley Ramirez, Anibal Sanchez, Harvey Garcia, and Jesus Delgado to the Florida (now Miami) Marlins in the winter of 2005, Josh Beckett was the prize.

Mike Lowell was seen as a salary dump by the Marlins and the Red Sox were derided for taking him and his big contract on. However, it turned out to be a blessing in disguise as both players were crucial in the Red Sox winning the 2007 World Series.

Beckett went 20-7 with a 3.27 ERA and 194 strikeouts in the regular season. He was even better in the 2007 postseason, going 4-0 with a 1.07 ERA and 35 strikeouts between the ALDS, ALCS, and World Series.

Lowell wasn’t too shabby, either. During the regular season he hit .324 with 21 home runs and 120 RBI. He followed that up in October by hitting .355 with 2 home runs and 15 RBI. His .400 average in the World Series helped him win World Series MVP.

Both players were mainstays on the Red Sox for several more years. Lowell re-signed and played the rest of his career in Boston before retiring after the 2010 season. Beckett was a member of the “every other year” club (see: Rick Porcello) and pitched pretty well in Boston but he became a headache and clashed with fans and the media (he was David Price in Boston before David Price was in Boston).

Beckett was shipped out to the Dodgers in August 2012 along with Adrian Gonzalez and Carl Crawford in a massive salary dump that was the very definition of addition by subtraction. That trade itself is one of the best in Red Sox history because even though the Red Sox didn’t get any quality talent in return, they rid themselves of three headaches and a whole lot of salary commitments in one fell swoop.

Jason Bay

You don’t usually consider a trade where you get rid of one of the most feared sluggers in the league, but this trade was still a good one for the Red Sox.  After seven incredibly productive and successful seasons in Boston, Manny Ramirez‘ act was wearing thin and grating on his teammates, manager, and fans.

In addition to (allegedly) faking injuries and refusing to play when called upon, the breaking point was reached when Ramirez threw longtime Red Sox traveling secretary Jack McCormick to the floor in anger when he couldn’t get more than the allotted number of game tickets for his family.

The Red Sox promptly shipped Manny out to the Dodgers at the 2008 trade deadline in a three-team deal and in return got Jason Bay from the Pittsburgh Pirates. Bay was the polar opposite to Ramirez in terms of personality, calm and friendly and he immediately became a key contributor.

In 49 regular season games with the Red Sox in 2008, Bay hit .293 with 9 home runs and 37 RBI. He was even better in the postseason, hitting .412 with 2 home runs and 5 RBI in the ALDS and .292 with a homer and 4 RBI in the ALCS. For an encore, he had a fantastic 2009 season hitting .267 with 36 home runs and 119 RBI.

The Red Sox offered him a contract after the season in the hopes of keeping him in Boston long-term, but he instead went to free agency and left for the New York Mets. While Bay was initially thought of as the one that got away, it turns out the Red Sox got the best of him in 2008 and 2009.

He battled injuries and decreased production over his three years in New York before retiring in 2013 after a final season spent in Seattle. Still, his brief time in Boston and his monster 2009 helped Red Sox fans get over losing Manny (who ended up having his own issues with PEDs after leaving Boston).

Chris Sale

There’s been a lot of discussion lately over whether the Red Sox won or lost this trade and it’s understandable. After pitching great in 2017 and 2018 before running out of gas at the end of both seasons, Chris Sale struggled in 2019 until being shut down in August. He reported to spring training this year battling pneumonia before his elbow issues flared up again.

With his status up in the air as to whether or not he’ll need Tommy John surgery and the delay in the start of the 2020 season throwing everything into chaos, many fans and media members have declared that the Red Sox lost the Chris Sale trade. They point to the fact that this year marks the first year of the huge five-year extension the team signed him to last year.

That contract is increasingly looking like an albatross around the Red Sox neck. Still, it’s hard to quibble with a deal that netted the Red Sox one of the best pitchers in the game (when healthy) and resulted in a World Series championship in 2018.

The deal consummated in late 2016 sent prospects Yoan Moncada, Michael Kopech, Victor DIaz, and Luis Basabe to Chicago for Sale. Kopech pitched well in Chicago’s minor league system and was in the majors for a cup of coffee before missing the end of 2018 and all of 2019 due to having Tommy John surgery. He was poised to pitch in the majors in 2020 before the start of the season was suspended.

Meanwhile, the White Sox rewarded Moncada for his 2019 season (.315 BA, 25 HR, 79 RBI)  by signing him to a five-year, $70 million extension. That led many Red Sox fans to view the trade as a loss for the team, but it’s hard to argue against a World Series win even if Sale is injured for the next season (or beyond).

Depending on how his extension ends up panning out will go a long way toward the general perception of whether Boston won or lost this trade. However, if the extension can be decoupled from the initial trade that brought him to Boston and what Sale did in 2017 and 2018 for the Red Sox, the deal itself can’t really be seen as anything other than a complete success.