Andrew Benintendi is the highest paid Chicago White Sox player in franchise history but hasn’t lived up to the hype. Can he bounce back in 2025 and be the star the Chicago White Sox signed him to be?
The Chicago White Sox former All-Star outfielder Andrew Benintendi to shine in 2025. Having not lived up to the hype of his contract that the Chicago White Sox gave to him back in 2023. Signing the former Gold Glover to a five-year $75 million deal to be a key pillar to their success, so far Benintendi has not met the expectations.
Sadly, it’s not all of Benintendi’s fault being that he signed with the White Sox when they were looking to be one of the top teams in the American League with a core of players like Tim Anderson, Yoán Moncada, Luis Robert Jr., Eloy Jiménez just to name a few names. What was supposed to be a great lineup never came into being with Yoán Moncada not being able to stay on the field due to injury, and both Eloy Jiménez and Tim Anderson having major drop offs offensively, the White Sox are now again in another rebuild.
Andrew Benintendi’s decade long career
The 2025 season will make a milestone in Andrew Benintendi’s career marking a decade playing baseball at the Major League level which is a feat we should applauded him for. The now 30-year-old Benintendi was the Boston Red Sox in the first round seventh overall of the 2015 MLB June Amateur Draft Benintendi have been a very solid and productive big-leaguer during his career. Earlier in his career Andrew Benintendi was looking to be one of the bright new superstars the game of baseball had to offer.
For the first seven years of his career, you couldn’t find a list of the top leftfielders in baseball and not have Benintendi’s name be either right in the middle of the list of being close to the top, which is why both the Kansas City Royals, and the New York Yankees found value in trading for him back in 2022 which is what lead him to inking his lucrative deal with the Chicago White Sox.
Andrew Benintendi’s career with the Chicago White Sox
In his two years so far since signing with the White Sox Benintendi has not lived up to his contract with 2024 marking the worst season statistically in his career. Playing in 135 games Benintendi had 109 hits, 20 doubles, 20 HRs, 64 RBI, for a slash line of .229/.289/.396 for and OPS and OPS+ of .685 and 95. Even though Benintendi’s numbers look bad there are signs that he can turn it around with being in the 93rd percentile for squared-up percentage so he is putting the good part of the bat on the ball.
Signing to join a team that was supposed to be in the playoffs for most of this decade immediately shifted into being the worst team Major League Baseball has ever seen. Talk about a real 180 for a player to have happen to him.
What is Andrew Benintendi’s future with the White Sox?
The Chicago White Sox will most likely have yet another 100-loss season in 2025 in which they figure to be one of the worst teams in baseball with having extremely strong competition from the Miami Marlins who really want that moniker. Having three-years left on his deal (including this season) in which he is owed $49.3 million the White Sox will need to figure out what to do with Benintendi. Will they keep him, or will he be traded at some point this season?
As I said the White Sox are in a rebuild which means they will look to play as many of their young prospects as they possibly can. Given Benintendi is owed that amount money and the White Sox having some outfield prospect that could figure to be here before Benintendi’s contract is up, the White Sox may take this season to see where Andrew Benintendi’s trade value stand.
If Andrew Benintendi can get back to the player he was back in 2022, then that should bode well for both Andrew Benintendi and the Chicago White Sox. If that can happen, then the White Sox will have a good number of teams calling them to try and trade for Benintendi, given he would be under control still for two and a half more seasons if he was traded at this year’s trade deadline.
What will happen to Andrew Benintendi in 2025?
I don’t foresee Andrew Benintendi being a part of the Chicago White Sox plans past 2025. If he is, I would be very surprised. The White Sox have a lot of promising young players that figure to push Benintendi out of a position given he is now getting into his thirties. With the White Sox figuring to realistically be good at maybe the earliest as 2027 given how fast some of their prospects are rising through the organization, keeping Andrew Benintendi for the full term of his deal would not be smart from a rebuilding perspective.
There is an outside chance that the White Sox could surprise baseball fans and be a surprise team to watch in 2026 and may be competitive for the National League Central title. However, that does not seem likely given we don’t know how some of their prospects will pan out.
Hopefully for both Andrew Benintendi and the Chicago’s White sake has a good season so hopefully he can get traded to a contender, which is what I think he needs to get back to the player he was, and for the White Sox to get prospects back to help with the rebuild.
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