Bleday grew up in Titusville, Pennsylvania, and attended Titusville Area High School as a freshman and sophomore before transferring to A. Crawford Mosley High School in Lynn Haven, Florida for his junior and senior years.

[4] That summer, he played for the Newport Gulls of the New England Collegiate Baseball League where he batted .232 with two home runs over 69 at-bats.

[10][11] He finished the season slashing .347/.465/.701 with 27 home runs and 72 RBIs during 71 games, helping Vanderbilt win the 2019 NCAA Division I baseball tournament.

[15][16] He made his professional debut on July 20, 2019, with the Class A-Advanced Jupiter Hammerheads of the Florida State League and spent the whole season there.

[24][25][26] Bleday ended the AFL with a .316/.435/.600 slash line over 25 games and was named the league's Hitter of the Year alongside Juan Yepez.

[28] He was assigned to the Jacksonville Jumbo Shrimp of the Triple-A International League to begin the year.

[32] On July 27, Bleday hit his first career home run, a solo shot off of Cincinnati Reds starter Luis Castillo.