Boston Red Sox’ Trade Deadline Approach

Boston Red Sox’ Trade Deadline Approach

by August 28, 2020 1 comment

The Boston Red Sox entered the season with playoff aspirations despite being in a tough division. However, things quickly fell apart for the 2018 World Series champions, who were dealt a blow when Eduardo Rodriguez was ruled out for the entire 2020 season due to a heart condition caused by COVID-19.

Boston also opened the year without Chris Sale, who underwent Tommy John surgery, leaving them without their top three starters from 2019. (Along with Rodriguez and Sale, the top three in the rotation was rounded out by David Price, who was sent to the Los Angeles Dodgers in the Mookie Betts trade.)

Sitting at 10-21 with just three games to go until the trade deadline, it will be critical for the Red Sox to not only assess their current roster but also their future plans. Trading away big-league-caliber players is a perfectly fine strategy but only if the team plans on committing to and following through with said retooling or rebuilding approach.

With that said, Boston must work on dumping any expiring or expensive contracts with a focus on the future. They’re likely not going to be a playoff team for the next four or five years even with the current roster, so they might as well dump a few MLB contracts in exchange for prospects who could make a difference come 2023 or 2024.

Before we dive into the full list of players that could be traded, it’s important to examine the untouchables. As the Red Sox have noted numerous times this summer, nobody is truly untouchable. With that said, it’s hard to imagine a situation where they trade Xander Bogaerts, Rafael Devers, or Michael Chavis. These three players have climbed through Boston’s systems and should keep their jobs long-term. Alex Verdugo likely won’t be traded, either.

The Red Sox have already made one move this summer, sending relievers Brandon Workman and Heath Hembree to Philadelphia in a move centered around bolstering the Phillies’ bullpen. This process of adding reliable bullpen arms will surely be replicated by other teams, and it wouldn’t be too surprising if the Red Sox made at least one more reliever trade.

Matt Barnes is the most interesting trade chip in the Boston bullpen. Promoted to closer following the Workman trade, Barnes appeared in at least 60 games every year from 2016 to 2019. Last season, he posted a 3.78 ERA over 70 games (64.1 innings), finished with a career-high 1.4 fWAR, and allowed 29 runs on 51 hits while striking out 110 and walking 38 batters. Barnes is making $1.15 million in 2020 (pro-rated) and has one more year arbitration before he is set to hit the open market.

While Barnes is the most attractive trade candidate out of Boston’s many relievers, other potential fits include Ryan Brazier (free agent after 2020), Josh Osich (2022), Ryan Brasier (2020), and Austin Brice (2023). Finally, 28-year-old Phillips Valdez‘s name could come up in trade talks, too. The first-year Red Sox right-hander has a 0.98 ERA and is set to hit free agency after this year, making him a great rental option for teams down the stretch.

Beyond the bullpen, the Red Sox could look to trade from their depleted starting rotation but might not receive much interest in return. Nathan Eovaldi has proven to be a reliable arm in the past, but his 4.98 ERA through six starts is not desirable, nor are the two years and $32 million that will remain on his contract after this season. Martin Perez is the only other tradable starter in Boston, and although he started off shaky, he has bounced back and could be a reasonable trade piece. Through six starts, he has a 3.45 ERA. Plus, he’s owed just $2.22 million this year and has a club option for 2021 at $6.25 million ($500K buyout).

Behind the dish, Christian Vazquez has built a name for himself as a solid offensive weapon with defensive success, too. He hit .276/.320/.477 in 2019 and is following that up with a .260/.295/.430 line through 28 games so far this year. He’s making just $1.55 million this year but will see his salary increase to $6.25 million next year. He also has a club option for the 2023 season that can be declined for $250K or exercised for $7 million. Vazquez’s name has been linked to teams like the San Diego Padres and Los Angeles Dodgers, who are gearing up for a playoff push and need to shore up their play behind the dish.

In the infield, Mitch Moreland continues to be a reliable offensive weapon, but it’s hard to see the Red Sox trading him at this point. The only other infielder who will garner legitimate trade interest is Jose Peraza. Signed by Boston in December, Peraza looked to bounce back in Boston after a down year with the Reds in 2019. He’s hitting just .241 so far and reaching base in just 29.8 percent of plate appearances, but he’s a reliable veteran presence who would make a good bench addition for several contenders. He’s making just $1.06 million this year and is arbitration-eligible for the next two seasons.

But wait, there’s more. Boston’s four outfielders are all candidates to be traded this summer, with Andrew Benintendi and Jackie Bradley Jr. likely at the forefront of Boston’s upcoming trade talks.

Benintendi, whose worst slash line from 2016 to 2018 was .271/.352/.424, saw a small statistical decline in 2019 (.266/.343/.431) before a much greater decline took place to open the 2020 season. Benintendi, who was placed on the 10-day IL on Aug. 12, was slashing a measly .103/.314/.128 in 38 at-bats prior to his rib injury. He had three singles and a double, adding one RBI, striking out 17 times, and recording 11 walks. Benintendi’s name has come up in trade rumors for the past few seasons and remains a prevalent name in Red Sox headlines yet again this year. He’s set to make $6.6 million in 2021, will be arbitration-eligible in 2022, and become a free agent ahead of the 2023 season. His down start to the season and nagging rib injury makes him a tough player to trade, but how long can Boston wait for him to improve his value?

Speaking of players whose names have frequented the rumor mill, Bradley has been a trade candidate for nearly five years but has stuck around in Boston thanks to his elite-level defensive prowess and occasional offensive streaks. With a .236/.317/.408 slash line in 845 games, it’s fair to say Bradley’s offense is the reason no team has pulled the trigger on trading for him. On the other hand, his defense is what keeps him in Boston’s lineup day in and day out. In 6,507.2 MLB innings, Bradley has made just 12 fielding errors and five throwing errors. He’s made 1,728 putouts, turned 18 double plays with his cannon of an arm, and has a 44 DRS to go along with his 27.0 UZR. Bradley has amassed a career fWAR of 13.4, with 40.4 coming via his defense and -15.4 from his offense. A well-regarded homegrown member of Boston’s outfield, Bradley is set to hit free agency this offseason and will surely come cheap for teams looking to shore up their outfield down the stretch.

The final two trade candidates in Boston’s outfield are slugger J.D. Martinez and journeyman defensive wizard Kevin Pillar.

A career .292/.356/.533 hitter, Martinez signed a five-year, opt-out-laden contract with Boston ahead of the 2018 season, meaning he controls his fate through 2022. Martinez was making $23.75 million in each of his first three years in Boston, but that value is set to drop to just $19.35 million in each of the final two seasons of the deal, leaving him in a solid position to opt out and sign with a new team if he desires to do so. Martinez posted 5.9 fWAR in his first year in Boston and 3.2 in Year 2, only to see that value take a dramatic fall to -0.4 through 29 games this year. In 124 plate appearances, he’s hitting just .213/.306/.380 a .253 BABIP, .298 wOBA and 82 WRC+. His three home runs equate to a pace of just six dingers in a 60-game season (or just 16 in a 162-game campaign). Boston has a tough decision to make as they could hold onto him and wait for his value to rise, thus making him a top trade target next summer, but they would run the risk of losing him to an opt-out this offseason.

Finally, Pillar landed with Boston this offseason on a one-year, $4.25 million (pro-rated at $1.57 million) deal after a 2019 season that saw him get traded from Toronto to San Francisco. He’s off to an impressive start, slashing .257/.316/.419, a line that checks in right above his career average of .260/.297/.405. His 0.4 fWAR equates to 2.2 in a 162-game season, which would finish as his third-best single-season fWAR. Pillar has been a reliable option for Boston both in the field and at the plate, and he is sure to garner trade interest in the next few days.

When all is said and done, Boston needs to enter and exit the trading period with a clear plan for their future. If they opt for rebuilding, which they should, they should aggressively shop players like Vazquez, Martinez, Pillar, Benintendi, Perez, Barnes, Bradley, and perhaps even Eovaldi. While they won’t be able to trade all of them, their ideal scenario should feature at least three of these players being traded.

Which three?

Well, trading any three of the above bunch would suffice, but the two that would land the biggest return would be Vazquez and Martinez, so they are the clear top choices. Parting with the nasty contracts of Bradley and Eovaldi won’t be easy, but shipping off Benintendi, Barnes, Perez, and Pillar should be considered doable.

Chaim Bloom was brought into Boston this past offseason to turn the organization around. The team knew they were in a tricky situation. On the heels of a horrible season in which they underachieved in their attempt to defend their World Series title, the Red Sox fired general manager Dave Dombrowski and had no choice but to part with manager Alex Cora, too, during the peak of the Astros and Red Sox cheating scandal that saw one general manager and three field managers lose their jobs.

There’s a new era of baseball in Boston. Gone are the days of Mookie Betts, Andrew Benintendi, and Jackie Bradley Jr. outfield. It’s time to rebuild. Bloom is the guy for the job, and he should be busy over the next few days.


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Andersen is a teenage sportswriter and reporter whose articles have appeared across the Prime Time Sports Talk, Sports Illustrated Kids, FantasyPros, and SB Nation platforms. He has also received credit from RotoWorld, CBS Sports, ESPN, Bleacher Report, USA Today, Yahoo Sports, The Athletic, SB Nation, NBC Sports, NY Post, and dozens of other sports sites for his reporting work.

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