Kenyan Middleton, who was traded to the Yankees from the White Sox at the deadline, blasted his now-former team. Photo Credit: Brett Davis-USA TODAY Sports Jul 15, 2023; Atlanta, Georgia, USA; Chicago White Sox relief pitcher Keynan Middleton (99) reacts after an out against the Atlanta Braves in the eighth inning at Truist Park. Mandatory Credit: Brett Davis-USA TODAY Sports

After wrapping up a four-game series against the Houston Astros on Sunday, the New York Yankees are set to embark on a three-city road trip. It will start against the Chicago White Sox on Monday.

That series will mark the return to Chicago for Kenyan Middleton, who was acquired by the Yankees at the trade deadline. And it’s safe to say that Middleton was happy about the trade.

Middleton was not with the White Sox for a long time. He signed a minor league deal with Chicago in the offseason, was promoted to the majors early in the year, then was traded to New York. But Middleton’s time with the White Sox left him with a big — and largely negative — impression.

“We came in with no rules,” Middleton said, per Jesse Rogers, ESPN. “I don’t know how you police the culture if there are no rules or guidelines to follow because everyone is doing their own thing. Like, how do you say anything about it because there are no rules? “You have rookies sleeping in the bullpen during the game. You have guys missing meetings. You have guys missing PFPs [pitcher fielding practices] and there are no consequences for any of this stuff.”

The White Sox reached the postseason in the COVID-shortened 2020 season, then won the American League Central in 2021. And while both postseason trips resulted in first-round eliminations, it seemed as though the team had turned a corner and that the many top prospects that were acquired in the late-2010s had turned into a core that would help the team be a consistent American League contender for a while.

But the last two seasons have largely dashed those hopes. The White Sox were a mediocre 81-81 in 2022. And while the Minnesota Twins lead the AL Central with a pedestrian 59-54 record, Chicago is 14 games out.

There was a critical difference between 2022 and 2023. The 2022 season was the last for manager Tony LaRussa. In 2023, he was replaced by Pedro Grifol. But despite the change in leadership, Middleton noted that he was told that a lot of the issues he had in 2023 were also there in 2022.

“When I got to spring training, I heard a lot of the same stuff was happening last year,” Middleton said. “It’s happening again this year, so not sure how I could change it. They don’t tell you not to miss PFPs. They don’t tell you not to miss meetings and if it happens, it’s just, ‘OK.'”

And this year in particular, he felt that some of the team’s better players being away at the World Baseball Classic was detrimental.

“If you’re trying to create culture, you need your big dogs,” Middleton said. “The guys who played in the WBC were our big dogs, and those are the guys I feel like can police the things that are happening…There was no gelling of the team. We’re supposed to find our identity in spring training so we can roll out for the season. If you don’t find your identity, you’re scuffling from Day 1.”

Middleton’s new team, the Yankees, has a longstanding policy against long hair and beards. That policy has come under heavy scrutiny in recent seasons, especially as it relates to traded players, who may have had no say in joining the team.

Middleton had a beard before the trade. But shaving his face being a prerequisite to playing on the Yankees was not an issue for him.

“The second I found out I was traded, I shaved my face,” Middleton said. “I was ready to play by their rules because all I want to do is win games. … You know how to act [here]. You know not to be late and you know there are consequences if you are late.

“You hear about it before you come over here,” Middleton said. “Did I want to shave my beard off? Hell no. I had to. I wanted to be a part of [the Yankees]. There was no question.”


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