The Chicago Cubs added Andrew Kittredge to their bullpen from the Baltimore Orioles ahead of the MLB trade deadline.
He didn’t have to go too far to change sides when he heard about the news because the Orioles were already on the way to Chicago to face off against the Cubs.
The two teams are set to play a three-game series beginning on Friday, meaning Kittredge will be wasting no time facing off against his former teammates.
It will be a fun and unique experience for the veteran right-hander, who was on the Baltimore team flight to Chicago on Wednesday night. Today, he was at the hotel for 30 minutes before learning about the trade that he was involved in.
As a result, he changed hotels and is now preparing to get out the same batters he has been working with all season.
As shared by Jesse Rogers of ESPN , Kittredge has a former teammate that he cannot wait to face off against and wants to get out the most this weekend: Gunnar Henderson.
New Cubs reliever Andrew Kittredge is here at Wrigley. Flew in with the Orioles last night. Was in his hotel for 30 min. Told of the trade and switched hotels. Picked Gunnar Henderson as the Oriole he wants to get out most this weekend.
— Jesse Rogers (@JesseRogersESPN) July 31, 2025
He could certainly get his wish, as Kittredge could quickly be inserted into a high-leverage role by manager Craig Counsell given his vast experience.
If he were called upon to face off against the star shortstop, retiring him would be easier said than done. Henderson, who got off to an incredibly slow start after beginning the campaign on the injured list, has a .285/.354/.464 slash line with 12 home runs, 25 doubles and four triples to go along with 43 RBI and 14 stolen bases.
There has been only one matchup between the 2024 AL All-Star and Kettridge previously; the veteran pitcher got the most of the young star, getting him out in their only at-bat against each other.
Kittredge, who also began the season on the injured list, has thrown well for the Orioles in 2025 in 31 appearances.
He has 31.2 innings pitched with 32 strikeouts, producing some of the best strikeout and walk rate numbers of his career.
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