O'Brien signed with the Rays and made his professional debut that year with the Princeton Rays of the Advanced Rookie Appalachian League,going 1–0 with a 2.20 ERA over 11 games (ten starts).[8] During the season,he was named Appalachian League Pitcher of the Week twice.[9] In 2018,he began the season with the Bowling Green Hot Rods of the Single–AMidwest League (with whom he was named an All-Star) before being promoted to the Charlotte Stone Crabs of the High–AFlorida State League,with whom he ended the year;over 25 games (13 starts) between both teams,he went 8–4 with a 2.75 ERA.[10][11][12] In 2019,he began the season with Charlotte and was promoted to the Montgomery Biscuits of the Double–ASouthern League in May. Over 20 games (17 starts) with the two clubs,he pitched to a 7–6 record and 3.16 ERA.[13]
O'Brien did not play in a game in 2020 due to the cancellation of the minor league season because of the COVID-19 pandemic.[14]
Cincinnati Reds
On August 28,2020,the Rays traded O'Brien to the Cincinnati Reds in exchange for Cody Reed.[15][16] On November 20,2020,the Reds added O'Brien to their 40-man roster to protect him from the Rule 5 draft.[17] To begin the 2021 season,he was assigned to the Louisville Bats of the Triple-A East.[18] Over 23 games (22 starts),O'Brien pitched to a 7–7 record,a 4.55 ERA,and 121 strikeouts over 112+2⁄3 innings.[19]
On September 28, 2021, the Reds recalled O'Brien to the active roster to make his MLB debut versus the Chicago White Sox.[20][21] He was the starting pitcher and threw 1+1⁄3 innings, giving up two solo home runs while walking three and striking out two.[22]
On April 13, 2022, the Reds designated O'Brien for assignment to make room for Nick Lodolo.[23]
Seattle Mariners
On April 16, 2022, the Reds traded O’Brien to the Seattle Mariners for cash considerations or a player to be named later.[24] (On June 3, minor league infielder Luis Chevalier was sent to Cincinnati to complete the trade).[25] He was designated for assignment on May 27. He cleared waivers and was sent outright to the Triple-A Tacoma Rainiers on June 2.[26]
O'Brien spent the entirety of the 2023 season in Triple–A with Tacoma. In 51 appearances, he registered a 2.29 ERA with 86 strikeouts and 15 saves across 55.0 innings of work.[27]
St. Louis Cardinals
On November 5, 2023, O'Brien was traded to the St. Louis Cardinals and subsequently added to the 40–man roster.[28] On March 26, 2024, the Cardinals officially revealed that O'Brien had made the Opening Day roster. On March 31, he was placed on the injured list with a flexor strain,[29] and was transferred to the 60-day injured list on May 6.[30] O'Brien was activated on August 11.[31]
Personal life
Riley is married to Chellyn O'Brien, they had their wedding in late 2023. O'Brien's grandfather, Johnny O'Brien, played six seasons in the major leagues.[21] His great uncle Eddie O'Brien also played in the majors.[32]
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