Triolo made his professional debut with the West Virginia Black Bears of the Low–ANew York–Penn League where he batted .239 with two home runs and 34 RBIs over sixty games, in which he played 41 games at third base and 17 games at shortstop.[5][8] He did not play a game in 2020 due to the cancellation of the minor league season because of the COVID-19 pandemic.[9] He played the 2021 season with the Greensboro Grasshoppers of the High-A East, slashing .304/.369/.480 with 15 home runs, 42 RBIs, 29 doubles, and 25 stolen bases over 108 games, in which he played 102 games at third base and five games at shortstop.[10] He was awarded a Minor League Gold Glove for his defense at third base.[11] He was assigned to the Altoona Curve of the Double-AEastern League for the 2022 season.[12] Over 112 games, Triolo slashed .282/.376/.419 with nine home runs, 39 RBIs, and 24 stolen bases, in which he played 87 games at third base, 17 games at shortstop, and seven games in center field.[13]
On November 15, 2022, the Pirates selected Triolo's contract and added him to the 40-man roster to protect him from the Rule 5 draft.[14] Triolo was optioned to the Indianapolis Indians of the Triple-AInternational League to begin the 2023 season.[15] On March 27, 2023, it was announced that Triolo would undergo surgery to address a fractured hamate bone in one of his wrists and miss multiple months in recovery.[16] Once he returned, Triolo played in 41 games split between the Single–A Bradenton Marauders and Indianapolis, hitting a cumulative .309/.412/.463 with 1 home run, 24 RBI, and 8 stolen bases, playing 32 games at third base, 16 games at shortstop, nine games at second base, and three games at first base.[5] On June 27, he was promoted to the major leagues for the first time following an injury to Ke'Bryan Hayes.[17]
