The Cleveland Indians selected Merryweather in the fifth round of the 2014 Major League Baseball draft.[3] He made his professional debut with the Mahoning Valley Scrappers going 1–2 with a 3.66 ERA in 13 games. He pitched 2015 with the Lake County Captains, posting a 4.08 ERA in 702⁄3 innings, and 2016 with the Lynchburg Hillcats and Akron RubberDucks,[4] going a combined 13–6 with 2.60 ERA in 24 games started between both teams. Merryweather started 2017 with Akron and was promoted to the Columbus Clippers during the season.[5][6] In 25 total games between Akron and Columbus, Merryweather pitched to a 7–9 record and 5.32 ERA.[7] The Indians added him to their 40-man roster after the season.[8]
Merryweather injured his pitching elbow during the Indians' 2018 spring training camp. The Indians subsequently announced he would need Tommy John surgery and would miss the entire 2018 season.[9]
Merryweather made his major league debut on August 20, 2020 against the Philadelphia Phillies.[13] On August 26, he made his first MLB start.[14] With the 2020 Toronto Blue Jays, Merryweather appeared in 13 games, compiling a 0-0 record with 4.15 ERA and 15 strikeouts in 13 innings pitched.[15]
On May 5, 2021, Merryweather was placed on the 60-day injured list with an oblique strain.[16] On September 8, Merryweather was activated off of the injured list.[17] He made 13 appearances for Toronto, posting a 4.85 ERA with 12 strikeouts and 2 saves.
On July 2, 2022, Merryweather was placed on the 60-day injured list with an oblique injury.[18] He was activated on September 5.[19] He made 26 total appearances for Toronto on the year, posting a 6.75 ERA with 23 strikeouts in 26+2⁄3 innings pitched.
On January 17, 2023, Merryweather was claimed off waivers by the Chicago Cubs.[21] In 69 games out of the bullpen, he registered a 3.38 ERA with 98 strikeouts across 72 innings of work.
In 2024, Merryweather began the year as part of Chicago's relief corps, posting a 1.93 ERA across 4 contests. However, he suffered a right shoulder strain and was placed on the injured list on April 7, 2024.[22] After undergoing additional testing, he was diagnosed with a rib stress fracture in his back,[23] and was transferred to the 60–day injured list on April 17.[24] Merryweather was activated from the injured list on July 22.[25] In 15 total games for Chicago, he struggled to a 6.60 ERA with 14 strikeouts across 15 innings pitched. On September 19, it was announced that Merryweather would undergo a patellar tendondebridement surgery on his knee, ending his season.[26]
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