Chicago White Sox: Three trade packages for Andrew Benintendi

FT. MYERS, FL - FEBRUARY 19: Andrew Benintendi #16 of the Boston Red Sox poses for a portrait during team photo day on February 19, 2020 at jetBlue Park at Fenway South in Fort Myers, Florida. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
FT. MYERS, FL - FEBRUARY 19: Andrew Benintendi #16 of the Boston Red Sox poses for a portrait during team photo day on February 19, 2020 at jetBlue Park at Fenway South in Fort Myers, Florida. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
2 of 4
Next
(Photo by Billie Weiss/Boston Red Sox/Getty Images)
(Photo by Billie Weiss/Boston Red Sox/Getty Images) /

At this point, you probably have already heard the rumors surrounding Boston Red Sox outfielder, Andrew Benintendi. He is apparently being shopped around and there is speculation that a trade might be imminent. The Chicago White Sox are at the point where they should be at least in on every big rumor like this because they are so close to being a World Series contender. If they added a kid like Benintendi to their group right now, he would be a cheap way to improve their depth.

Benintendi coming over a few years ago would have really appeared to grow this group’s chances of taking the next step. Now, you have to wonder what sort of impact it would have because things haven’t gone as smoothly for him since his awesome 2018 season. 2019 wasn’t as terrible as some make it out to be but 2020 was a disaster.

2020 wasn’t necessarily all his fault, either. The Boston Red Sox were a terrible baseball team just two years after winning their fourth World Series title in just under 15 years. Benintendi also was hurt for most of the year as he played in 14 games. Nobody should really take much stock in his injured season during a pandemic but he really wasn’t good in those 14 games.

The Chicago White Sox would really like to add Andrew Benintendi if the price is right.

The White Sox would be smart to take a chance on Benintendi if the Red Sox are really shopping him for cheap. The White Sox could use the extra outfield depth and the Red Sox are trying to rehaul their entire organization. There are a lot of great pieces that may never have a chance with this team that Boston can take advantage of. These three trade packages might be enough to get it done:

(Photo by Billie Weiss/Boston Red Sox/Getty Images)
(Photo by Billie Weiss/Boston Red Sox/Getty Images) /

The Chicago White Sox might have to give up some good pitchers in a trade.

Trade One

The Chicago White Sox could use some help in the outfield. Adding Andrew Benintendi could really go a long way in doing that. It also opens the door for them to try Eloy Jimenez as a designated hitter. They all can hit so if they come up with a roster including all of the outfielders that are awesome hitters, the run-scoring potential is off the charts. After that, it would be about managing them in the lineup and in the field to make sure they are getting the most out of them.

For that reason, trading Jonathan Stiever and Matthew Thompson to the Red Sox in exchange for Andrew Benintendi could work out to be a great move. Boston doesn’t have great pitching depth within the organization anymore but adding two mid-level prospects like this is exactly what they need. Neither of them is likely to become Chris Sale or anything like that but they could become great depth starters for a long time.

Stiever already has some MLB experience with the White Sox so the Red Sox would be able to start developing him at the MLB level right away. As for Thompson, he is the White Sox number seven prospect who has a few years before he is going to make a significant impact. The Red Sox are going to be going through a rebuild that may take a long time so adding two young pitchers like this should really help that along.

(Photo by Billie Weiss/Boston Red Sox/Getty Images)
(Photo by Billie Weiss/Boston Red Sox/Getty Images) /

Some position players could get Andre Benintendi to the Chicago White Sox.

Trade Two

There could be a world where the Red Sox want position-playing prospects for Andrew Benintendi. The White Sox wouldn’t trade Andrew Vaughn or Nick Madrigal and they are the only two non-pitchers in their top seven prospects so that leaves Gavin Sheets and Micker Adolfo. The Red Sox would be wise to go for players like these two if they are going to trade Benintendi. It really wouldn’t hurt the White Sox and their future plans all that much but it could really help Boston add some young depth to their organization.

Micker Adolfo is listed as the White Sox number eight prospect. He is an outfield prospect who could eventually grow into a guy who can play the position for them in the place of Benintendi. They also might not have Jackie Bradley Jr. for much longer and Mookie Betts is already gone. They really might be smart to start looking to fix their outfield and Adolfo has a high enough ceiling to take a chance on.

As for Sheets, he is a guy that can play first base and right field. He is the White Sox number nine prospect after they drafted him in the second round of the 2017 MLB Draft. He could add some much-needed depth to Boston’s organizational infield. With Jose Abreu already there winning MVPs and Andrew Vaughn on the way, it doesn’t seem like the White Sox are going to need a player like him anymore.

(Photo by Billie Weiss/Boston Red Sox/Getty Images)
(Photo by Billie Weiss/Boston Red Sox/Getty Images) /

A haul of lower-tier Chicago White Sox prospects could land them Andrew Benintendi.

The Chicago White Sox have a window here where they can win the World Series. They already look like the undisputed favorite to win the American League Central. That is a big step towards winning the World Series because they will be in the playoffs with home-field advantage. If they can just add some more depth on the bench and to their starting rotation, they should be off to the races.

Andrew Benintendi has World Series-winning experience which is something that is big-time lacked by this White Sox team. They have all the talent in the world but most of them have played in a grand total of three playoff games. Some veteran leadership that has won in the past would go a long way, especially if they aren’t even that old.

The White Sox might be willing to send away a big haul in order to get that type of player. If they did trade away four players, they probably wouldn’t be top-ten White Sox prospects but there is still some quality in this trade package. Blake Rutherford, Jake Burger, Jimmy Lambert, and Seby Zavala are all players who don’t have the highest ceiling but they could be good MLB players. They also all play different positions so the Red Sox would be adding some great depth at all different positions.

Hot. Yasmani Grandal is the second-best catcher in the world. light

If Andrew Benintendi is in fact available, we have no clue what the team acquiring him would need to give up so this is all a guess. Trade one suggests two pitching prospects in Chicago’s top ten, trade two is two position players in Chicago’s top ten, and trade three is a four depth prospects. If the White Sox added someone like Benintendi, there is a good chance that it really improves their depth.

Next