Keynan Anthony Middleton (born September 12, 1993) is an American professional baseball pitcher for the Long Island Ducks of the Atlantic League of Professional Baseball. He has previously played in Major League Baseball (MLB) for the Los Angeles Angels, Seattle Mariners, Arizona Diamondbacks, Chicago White Sox, and New York Yankees. Middleton was drafted by the Angels in the third round of the 2013 MLB draft and made his MLB debut with them in 2017.
High school and college
Middleton attended Milwaukie High School in Milwaukie, Oregon. He later played
college baseball at Lane Community College.
[ Keynan Middleton Stats, Fantasy & News | MLB.com] He was drafted by the Los Angeles Angels in the third round (95th overall) of the 2013 Major League Baseball draft.
Career
Los Angeles Angels
He made his professional debut with the Arizona League Angels and was promoted to the
Orem Owlz during the season.
Middleton spent 2014 with the Orem and played with the
Burlington Bees in 2015. He began the 2016 season with the Inland Empire 66ers and was subsequently promoted to the Arkansas Travelers and Salt Lake Bees. Between the three teams, he recorded a 1–2 record with a 3.41 ERA, averaging 12 strikeouts per 9 innings.
[ Keynan Middleton Minor Leagues Statistics & History | Baseball-Reference.com]
Middleton made his MLB debut on May 5, 2017, allowing a run while striking out one in an inning of work.
Middleton began the 2018 season as the closer for the Angels. On May 14, Middleton was placed on the disabled list for the second time in the year due to suspected damage to the UCL in his right elbow.[ Keynan Middleton Stats | Baseball-Reference.com] After rehabbing for most of the 2019 season, Middleton returned in September, appearing in 11 games. However, on December 2, he was nontendered by the Angels.
In 2020, Middleton was 0–1 with a 5.25 ERA.
Seattle Mariners
On December 16, 2020, Middleton signed an $800K major league contract with the
Seattle Mariners.
He appeared in 32 games for the Mariners, posting a 4.94 ERA with 24 strikeouts. On August 26, 2021, he was designated for assignment by the Mariners.
Two days later, on August 28, he cleared waivers and was assigned outright to the Triple-A
Tacoma Rainiers.
On October 8, Middleton elected free agency.
Arizona Diamondbacks
On January 13, 2022, Middleton signed a minor league contract with the Arizona Diamondbacks.
He was assigned to the Triple-A
Reno Aces to begin the year.
On April 29, Middleton had his contract selected to the 40-man and active rosters.
Chicago White Sox
On January 15, 2023, Middleton signed a minor league contract with the Chicago White Sox. He was assigned to the Triple-A Charlotte Knights to begin the year, recording three strikeouts in three scoreless innings pitched. On April 10, he had his contract selected to the active roster.
New York Yankees
On August 1, 2023, Middleton was traded to the New York Yankees in exchange for
Juan Carela.
He became a free agent following the season.
St. Louis Cardinals
On February 3, 2024, Middleton signed a one-year contract with the St. Louis Cardinals, that included a club option for the 2025 season.
He began the year in the injured list with a right forearm strain, later receiving a platelet-rich plasma injection; he would go on to make five rehab appearances for the Double-A Springfield Cardinals. On June 4, Middleton underwent season–ending surgery to repair his flexor tendon.
The Cardinals declined his option on October 31, making him a free agent.
Long Island Ducks
On July 11, 2025, Middleton signed with the Long Island Ducks of the Atlantic League of Professional Baseball.
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