[4] That summer, he played in various national events including the Perfect Game All-American Classic at Petco Park.

[18][19] Holliday made his professional debut on August 11 with the Rookie-level Florida Complex League Orioles, going 1-for-3 with a stolen base.

[22] Holliday began the 2023 season with the Shorebirds, where he batted .396/.522/.660 with six doubles, one triple, two home runs and 16 RBIs in 14 games.

[24] He hit .338/.421/.507 with nine doubles, three triples, three home runs, and 15 RBIs in 36 games with the Baysox before his promotion to the Triple–A Norfolk Tides on September 4.

[28] Invited to spring training in 2024 as a non-roster player,[29] the Orioles assigned Holliday to Norfolk for the start of the season.

[30] He batted .333/.482/.595 with two home runs through ten Triple-A games in 2024 and has a career .321 average and .949 on-base plus slugging (OPS) in Minor League Baseball.

7 uniform and made his major league debut that night as a second baseman[33] against the Boston Red Sox and went 0–4 with 1 RBI at the plate.

[36] Holliday slashed .259/.421/.455 with 20 doubles, eight home runs, and 29 RBI in 63 games with the Tides prior to being recalled by the Orioles for a second time on July 31.