Former White Sox Pitcher Keynan Middleton Lambastes Team’s Culture, Lack of Rules

Keynan Middleton, who was traded to the Yankees at the deadline, criticized the White Sox over the club’s “no rules” culture.

Yankees reliever Keynan Middleton has been with the organization for less than a week, but it seems he’s noticed some stark differences in how things operate in the Bronx compared to that of his former team, the White Sox.

Middleton was acquired by New York in a trade with Chicago at MLB’s trade deadline. 

Speaking with ESPN’s Jesse Rogers on Sunday, Middleton detailed the White Sox’ “no rules” culture, including a tidbit about a rookie pitcher who fell asleep in the bullpen on multiple occasions. 

“We came in with no rules,” said Middleton, who signed for Chicago ahead of the 2023 season. “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 ... there are no consequences for any of this stuff."

Prior to his trade to the Yankees, Middleton had made 39 appearances for the White Sox, registering a 3.96 ERA. The team has massively underperformed, sitting at 45–68 and in fourth place in the AL Central.

“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.”

Middleton suggested that leadership was responsible for the disastrous team culture in Chicago, indicating he had heard “a lot of the same stuff was happening last year.”