Holifield is a native of Fort Worth, having played his high school baseball for nearby Boswell. The 26-year-old right-hander put together an excellent campaign in 2019 with the Rockland Boulders of the Can-Am League, going 1-1 with a 2.79 ERA in 27 appearances, including three starts. Over 42.0 innings of work, Holifield allowed only 36 hits, picking up 53 strikeouts to just 13 walks (4.1:1 ratio). 10 of the 13 runs that Holifield allowed in 2019 came over the course of two outings, and the right-hander was unscored upon in 21 of 24 relief appearances.

The Railroaders initially acquired Holifield in exchange for right-handed pitcher John Shull following the 2019 season; when Shull elected to retire, the Railroaders sent left-handed pitcher Braden Pearson to the Boulders to complete the trade.

Holifield was selected by the Sioux Falls Canaries in the sixth round of the 2020 American Association Dispersal Draft, but did not play.

Holifield began his college career at Fort Scott Community College in 2013, where he spent two seasons with the Greyhounds. The 6’4, 230-pounder transferred to Abilene Christian University for his junior season, where he made ten appearances to the tune of a 4.34 ERA. Holifield sat out the 2016 season after transferring to Wichita State University, then made 17 appearances for the Shockers in 2017. He finished the year with a 3.95 ERA, striking out 20 in 13.2 innings. Over his first ten outings covering 11.0 innings, Holifield allowed only three hits and one run while striking out 18.

The Milwaukee Brewers signed Holifield as an undrafted free agent following the 2017 season, assigning him to their Rookie-level Arizona League affiliate. Holifield was off to a strong start as a professional, notching a 1.80 ERA in 17 relief appearances before an injury ended his season and sidelined him for the entirety of the 2018 campaign.