After graduating from Calallen,Zastryzny enrolled at the University of Missouri,where he played college baseball for the Missouri Tigers.[6] In three years at Missouri,Zastryzny had a 9–19 win–loss record and a 3.79 ERA with 228 strikeouts,the eighth-most in Tigers history.[7]
Zastryzny began the 2016 season with Tennessee,and received a mid-season promotion to the Iowa Cubs of the Triple–APacific Coast League. On August 19,the Cubs promoted him to the major leagues.[13] Zastryzny made 11 appearances for the Cubs to finish 2016,and finished 1-0 with a 1.13 ERA. The Cubs would eventually win the 2016 World Series,ending their 108-year drought. Zastryzny won his first World Series title.[14] Zastryzny was added to the roster for the 2016 National League Championship Series,replacing Tommy La Stella who had been on the roster for the 2016 National League Division Series.[15] Although eligible to play,he did not appear in any NLCS games. Zastryzny was replaced by Kyle Schwarber on the roster for the 2016 World Series.[16] He was designated for assignment on September 1,2018. He was outrighted to Iowa on September 3.[17] Zastryzny was released by the Cubs organization on March 25,2019.
Los Angeles Dodgers
On March 26,2019,Zastryzny signed a minor league contract with the Los Angeles Dodgers organization. In 23 games (19 starts) split between the Double–A Tulsa Drillers and Triple–A Oklahoma City Dodgers,he compiled a 4–8 record and 5.58 ERA with 104 strikeouts across 113 innings pitched. After the season,on October 8,he was selected for the Canada national baseball team at the 2019 WBSC Premier12.[18] Zastryzny elected free agency following the season on November 4.[19]
Baltimore Orioles
On November 26,2019,Zastryzny signed a minor league deal with the Baltimore Orioles organization.[20] Zastryzny did not play in a game in 2020 due to the cancellation of the minor league season because of the COVID-19 pandemic.[21] He spent most of the major league season on the team's 60-man alternate training site pool,but was released by the Orioles organization on September 18.[22]
On November 29, 2021, Zastryzny signed a minor league deal with the New York Mets.[27] On August 20, 2022, Zastryzny's contract was selected from Triple-A and was promoted to the major league roster. On August 21, Zastryzyny was optioned to the Triple–A Syracuse Mets. On August 22, Zastryzyny was designated for assignment.[28]
Los Angeles Angels
On August 25, 2022, Zastryzny was claimed off waivers by the Los Angeles Angels.[29] On November 15, Zastryzny was designated for assignment by the Angels after they protected multiple prospects from the Rule 5 draft.[30] On November 18, Zastryzny was non–tendered and became a free agent.
Pittsburgh Pirates
On December 22, 2022, Zastryzny signed a minor league deal with the Pittsburgh Pirates.[31] He had his contract selected on March 30, 2023. [32] In 18 appearances for Pittsburgh, he posted a 5.29 ERA with 13 strikeouts in 17.0 innings. After a brief stint on the injured list with left forearm inflammation, he was activated and promptly designated for assignment on July 7.[33] Zastryzny cleared waivers and was sent outright to the Triple–A Indianapolis Indians on July 10.[34] On August 24, Zastryzny was selected back to the major league roster.[35] He was designated for assignment again on September 4.[36] On September 8, he cleared waivers and elected free agency in lieu of an outright assignment.[37]
Milwaukee Brewers
On December 12, 2023, Zastryzny signed a minor league contract with the Milwaukee Brewers.[38] In 28 games for the Triple–A Nashville Sounds, he compiled a 3.18 ERA with 38 strikeouts and 2 saves across 28+1⁄3 innings pitched. On June 29, 2024, the Brewers selected Zastryzny's contract, adding him to their major league roster.[39] In 9 games for Milwaukee, he compiled a 1.17 ERA with 5 strikeouts over 7+2⁄3 innings pitched. Zastryzny was placed on the injured list with left elbow tendinitis on July 26,[40] and transferred to the 60–day injured list on September 12.[41]
New York Yankees
On November 4, 2024, Zastryzny was claimed off waivers by the Chicago Cubs.[42] He was designated for assignment by the Cubs on February 4, 2025.[43] On February 11, Zastryzny cleared waivers and was sent outright to the minors.[44] He subsequently rejected the assignment and elected free agency on February 13.[45]
On February 17, 2025, Zastryzny signed a minor league contract with the New York Yankees.[46] In 13 appearances for the Triple-A Scranton/Wilkes-Barre RailRiders, he recorded a 4.50 ERA with 12 strikeouts over 12 innings pitched.
Milwaukee Brewers (second stint)
On May 16, 2025, Zastryzny was traded to the Milwaukee Brewers in exchange for cash considerations; he subsequently had his contract selected and was added to Milwaukee's active roster.[47]
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