When Andrew Benintendi signed his five-year, $75 million deal, it became the most expensive contract in Chicago White Sox franchise history. However, the pact hasn’t led to many more wins.
Benintendi has tried to do his part, and was crucial in Wednesday’s 7-3 victory over the Arizona Diamondbacks. His first inning home run put Chicago on the board. Still, the win only moved the White Sox to 26-55. They haven’t made the playoffs since 2021 and are coming off of a historically bad 121 loss season.
Benintendi knows the White Sox are battling and he believes the team has a strong core in place. However, this wasn’t what he was expecting when he put pen to paper, via Scott Merkin of MLB.com.
“When I signed here, it was some big names and then it seemed like at the Deadline that year, they got rid of everybody,” Benintendi said. “Obviously we are in a rebuild, so when that happens, it kind of stinks because it feels like where I was in my career then, I want to be a part of a winning team and they make that move and it’s kind of disappointing. But it is what it is.”
“Last year, going through the 121 losses, I think everybody had a terrible time. You try to have fun, but in the end it kind of sucks losing that many games,” he continued. “This year, there seems like there have been signs of improvement as far as talent coming in here and young guys kind of got their feet wet last year learning more and becoming better. It seems like it’s kind of creeping back to hopefully the future is going to be better.”
Andrew Benintendi’s run with Chicago White Sox
Heading into the 2023 season, the White Sox were coming off of an 81-81 campaign and a second-place finish in the AL Central. It made sense to target a player of Benintendi’s stature. However, the wheels fell off mighty quick. Players like Jake Burger, Kendall Graveman, Lucas Giolito and Reynaldo Lopez were all traded away. Chicago embraced the tank and ended the year with a 61-101 record.
While the White Sox have rebuilt their farm system through a number of trades, namely moving Garrett Crochet to the Boston Red Sox, Benintendi now feels out of place. He is the highest paid player on the roster, but Chicago is clearly focused on developing their prospects. In turn, Benintendi’s contract makes him difficult to trade without the White Sox attaching a prospect or eating salary.
Furthermore, the outfielder’s play hasn’t been as consistent as it was during the early part of his career. He hit .262 in his first year with 13 home runs, although he only had five home runs and 45 RBI. Benintendi bumped it up to 20 home runs and 64 RBI in 2024, but with just three steals and a .229 batting average. Through the first 53 games of the 2025 season, the outfielder is hitting .236 with nine home runs and 30 RBI.
Benintendi’s deal hasn’t worked out how both player and franchise had planned. While it’s hard to complain about $75 million, it has been a while since the former All-Star has played meaningful baseball.
White Sox digging deeper into rebuild
When the 2025 MLB trade deadline rolls around, the White Sox will be amongst the most obvious sellers. Benintendi could be moved, but he isn’t deemed at the top of the list. Instead, most teams calling Chicago will be looking for Luis Robert Jr or pitching.
Robert has a pair of $20 million options left on his contract, helping and hurting his trade value. He has two more years of team control, but any acquiring franchise must be confident in a turnaround. While Robert has an impressive 22 stolen bases on the season, he is hitting a putrid .185 with eight home runs and 32 RBI. Robert is a true 20/20 threat if he is on top of his game. But the White Sox must convince an acquiring club that a change of scenery is all he needs.
Adrian Houser has been a revelation since coming to Chicago, holding a 2.27 ERA over his first six starts. As a free agent, the White Sox will see if they can get an intriguing prospect in return. The same goes for Aaron Civale, who came over in the Andrew Vaughn trade. His tenure on the South Side hasn’t been long, but a seasoned veteran on an expiring deal is primed to be dealt. Looking at the bullpen, veterans such as Tyler Alexander, Dan Altavilla and Steven Wilson could all be on the move.
To Benintendi’s disappointment, the rebuild trudges on. The White Sox will have a much better view of where they stand after the deadline.
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