The Los Angeles Dodgers selected Roller in the 30th round, with the 910th overall selection, of the 2017 Major League Baseball draft[3] and he signed with the Dodgers.[4] He made his professional debut for the rookie–level Arizona League Dodgers, hitting .181 in 45 games. Roller split the 2018 season between the rookie–level Ogden Raptors and Single–A Great Lakes Loons, where he played in 54 contests and hit a combined .274/.377/.458 with 6 home runs, 24 RBI, and 12 stolen bases.[5]
He returned to Great Lakes in 2019, playing in 88 games and batting .274/.359/.455 with 7 home runs, 44 RBI, and 10 stolen bases.[6] Roller did not play in a game in 2020 due to the cancellation of the minor league season because of the COVID-19 pandemic.[7]
Cleveland Indians/Guardians
On December 10, 2020, the Cleveland Indians selected Roller from the Dodgers in the minor league phase of the Rule 5 draft.[8] He returned to action in 2021 with the Double–A Akron RubberDucks, for whom he made 70 appearances and hit .203/.281/.281 with one home run, 27 RBI, and 14 stolen bases.[9]
Roller spent the 2022 season back in Akron, also appearing in three games for the Triple–A Columbus Clippers. In 76 games for Akron, he slashed .212/.308/.328 with 4 home runs, 26 RBI, and 6 stolen bases.[10]
Milwaukee Brewers
On August 31, 2023, Roller was traded to the Milwaukee Brewers in exchange for cash considerations.[11] In 108 games split between Columbus and the Triple–A Nashville Sounds, he batted a combined .247/.394/.449 with career–highs in home runs (15), RBI (67), and stolen bases (19).[12]
On October 23, 2023, the Brewers added Roller to their 40-man roster to prevent him from reaching minor league free agency.[13] He was optioned to Triple–A Nashville to begin the 2024 season.[14] The Brewers promoted him to the major leagues for the first time on May 15, 2024.[15] He made his MLB debut that night against the Pittsburgh Pirates, striking out against Luis Ortiz in his only at–bat. Roller was designated for assignment by the Brewers on June 29.[16] He cleared waivers and was sent outright to Triple–A Nashville on July 4.[17] On November 6, he elected free agency.[18]