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Boston Red Sox: Remembering the best trades in franchise history

By Drew Athans

OAKLAND, CA - APRIL 20: Jason Varitek #33 of the Boston Red Sox looks on from the dugout before the game against the Oakland Athletics at the Oakland-Alameda County Coliseum on April 20, 2010 in Oakland, California. The Red Sox defeated the Athletics 5-3. (Photo by Michael Zagaris/Oakland Athletics/Getty Images)
OAKLAND, CA - APRIL 20: Jason Varitek #33 of the Boston Red Sox looks on from the dugout before the game against the Oakland Athletics at the Oakland-Alameda County Coliseum on April 20, 2010 in Oakland, California. The Red Sox defeated the Athletics 5-3. (Photo by Michael Zagaris/Oakland Athletics/Getty Images) /
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(Photo by Jim McIsaac/Getty Images)
(Photo by Jim McIsaac/Getty Images) /

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).

Next. Red Sox Memories: Jon Lester's no-hitter. dark

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.

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