Winter Meetings: Red Sox should trade outfielder Andrew Benintendi

BOSTON, MA - JULY 30: Andrew Benintendi #16 of the Boston Red Sox returns to the dugout after hitting a two-run home run in the fifth inning of a game against the Tampa Bay Rays at Fenway Park on July 30, 2019 in Boston, Massachusetts. (Photo by Adam Glanzman/Getty Images)
BOSTON, MA - JULY 30: Andrew Benintendi #16 of the Boston Red Sox returns to the dugout after hitting a two-run home run in the fifth inning of a game against the Tampa Bay Rays at Fenway Park on July 30, 2019 in Boston, Massachusetts. (Photo by Adam Glanzman/Getty Images) /

With rumors surrounding Red Sox outfielders Betts and Bradley Jr., there is a case to be made that they should trade their left fielder, Andrew Benintendi.

Earlier in the offseason, Ken Rosenthal reported that it is “all but certain” a Jackie Bradley Jr. trade goes down this offseason. Mookie Betts has had his name thrown around since the beginning of October as he is one of the best players in the game and is set to make $27 million next year (per MLB Trade Rumors) while the Red Sox need to cut payroll.

With those two players being talked about being dealt, I believe that the Red Sox should contemplate trading their other outfielder. Andrew Benintendi was the number one prospect in Boston headed into 2016 and he pushed his way onto the roster. After impressing in 2016, he followed that up with runner-up AL Rookie of the Year in 2017.

He hit second for the majority of the 2018 season, in front of the eventual AL MVP. However, his production slipped in 2019 and he was a league-average offensive player (100 OPS+). With his strikeouts up and home runs down, Benintendi was a shell of his 2018 self.

His issues seem reversible as his problems stemmed primarily from his mechanics. However, he could be dealt to get a haul of prospects in return, or he could be used as a complementary piece if the Red Sox want to cut a player with a bad contract. Let’s go over a few scenarios why it makes sense for Benintendi to be dealt instead of Bradley or Betts.

He could be used as a sweetener

The Red Sox roster is filled with many bad contracts, specifically in the starting rotation. With a report from Alex Speier that the Red Sox would rather trade a starter than their MVP-caliber outfielder in Mookie, it would take a lot to trade a David Price or Nathan Eovaldi.

Both are set to make serious amounts of money over the next three years and their 2019 performance didn’t provide hope for the 2020 season. If the Red Sox want a team to relieve them of one of those bad contracts, Benintendi could be thrown in.

With the left-handed hitter included in a trade package, the Red Sox may get a better prospect package in return. Benintendi has three years of control left and his sweet swing may make a team even want to take on the challenge of Price or Eovaldi.  The other two outfielders can’t be thrown in because Betts makes too much money to be paired with Eovaldi or Price, and a team probably won’t want to pay JBJ $11 million if another large contract is included.

He helps long and short term

Benintendi has three years of control remaining while Betts and Bradley are headed into their final seasons. This means a team exiting a rebuild will have him for the next few years with their new core. For example, the Padres could pair Benintendi and Fernando Tatis Jr. together for the next three years and they could go all-in for those few years.

Betts and Bradley would cost prospects and only help out in the first year. The lefty could be the core of a club for years to come and help a new team emerge as postseason contenders. He also shouldn’t cost too much coming off of his average 2019 season.

It may be beneficial to trade him now because he could be worthless after 2020. If he puts up another league-average or poor season, teams will realize he is not as good as he was once projected to be. Trading a player after one down season will get you more back than after two down seasons.

He may end up being a bust in Boston

The Red Sox are still a win-now team headed into 2020. Based on his 2019 season, Benny is a league-average hitter with no guarantee to return to his prior form. Many teams still believe in his potential as he is nearly a complete athlete.

While his value is not as high as it was prior to 2019, he still will bring back a quality prospect or two. If he is not going to live up to his potential, then players like Sam Travis should be given a shot in left. Also, if he isn’t providing better than league-average hitting, he won’t help the Red Sox push to the 2020 postseason.


Benintendi has distinct advantages over the other two Red Sox outfielders. Betts and Bradley both only have one year of control left, Benintendi has three. Betts will make nearly $20 million more than Benintendi, Bradley $5 million more, and the left fielder will surely put up better numbers than JBJ.

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While it is very unlikely he is dealt, there is a case to be made that the Red Sox should explore trade options for the left fielder at the Winter Meetings. With a relatively weak outfield free agent class, Benintendi could bring back a solid return. While the Red Sox front office will believe the young left fielder can bounce back in 2020, if I was Chaim Bloom for a day, Benintendi would surely be dealt.