Should the White Sox Trade for Andrew Benintendi?

The Chicago White Sox should at least consider a potential trade for Andrew Benintendi.

Drafted seventh overall in 2015, Andrew Benintendi debuted for the Boston Red Sox in 2016. Many saw the potential for him to break out and be a star in left field in Boston for a long time. When reports came out that the Chicago White Sox dealt Chris Sale to Boston, some thought Benintendi could have been involved. However, the Red Sox kept their faith in him. Here we are four years later and the Red Sox have put him on the trade block.

The 26-year-old has, so far, had an up and down career in Boston. His first full season was in 2017. He hit a respectable .271/.352/.424 slash with an OPS of .776. Not stellar, but his 20 home runs and 90 RBIs went along with 20 stolen bases and opened up some eyes.

His 2018 was even better. He hit a batting slash of .290/.366/.465 with an OPS of .830. His power dipped a little, hitting only 16 home runs and 87 RBIs in 148 games. The trajectory of Benintendi’s career was rising and rising. In 2019, however, he would take a step backward.

He finished the season with a rough .266/.343/.431 slash with .774 OPS. He did play in ten fewer games, but his home run, RBI, and stolen base numbers dropped significantly to 13/68/10. A silver lining to take out his ’19 would be his 40 doubles, but besides his ability to find the gaps every now and then, he had a pretty lackluster season.

Early August 2020, Benintendi was placed on the injured list with a right rib cage strain so it is hard to tell where exactly he is in his development process. At the moment, the Red Sox are actively shopping around a left-handed 26-year-old outfielder with a high ceiling and some successful experience in the league.

The elephant in the room would be where he plays if the White Sox were to trade for him. He is a left and center fielder with little to no right field experience, which is not ideal for the team at this moment. Even though Adam Eaton was signed this offseason, right field and designated hitter are the two positions the team needs to address the most.

Of course, the most obvious fix would be shifting Eloy Jiménez into the DH role and putting Benintendi in his place. However, Jiménez has expressed his disinterest in DHing and how he wants to be in the field. When he was asked if he would DH, he said no.

If Jiménez does not improve defensively, the DH role might be what he has to take on. It’s Tony La Russa’s decision at the end of the day and if Jiménez is costing the team runs in the outfield, we all know he will not hesitate to fix the situation regardless of anyone’s feelings.

Another option the Sox can do is try out Benintendi in right field, but it is unclear if that is a possibility. The last time Benintendi was in right was in 2014 for the Arkansas Razorbacks. He played 29 games there and that is it. Some say there is not much of a difference between left and right, and perhaps that is true, and it may be true for Benintendi.

As for the price, it seems as if the Red Sox are looking to get a name or two they can rebuild around headed forward. Pitching is an obvious necessity for Boston and it always has been. It has also been reported they would be interested in outfielder prospects as well.

Behind Michael Kopech and Garret Crochet, the next top White Sox pitching prospects are Jared Kelley, Jonathan Stiever, and Matthew Thompson. It is possible that a trade package would involve one if not two of these names.

As far as the outfield, the White Sox are a bit thin in terms of depth. The highest-rated prospect in the outfield is Micker Adolfo. Behind him are Luis González and Blake Rutherford. Again, one if not two of these names could be involved in the deal.

If giving up some prospect depth is the price to pay for Andrew Benintendi, it might be worth it. He has the capability to perform at a high level and he has proven that. He is a former top 10 pick who so far has had just one bad year if you chose to overlook 2020.

That being said, it is a bit strange for Boston to put him on the trade block. By the looks of the reports, it seems Benintendi might not be a Red Sox by the end of the weekend. Regardless, when a player of his caliber becomes available, it must at least be considered.