Waldron attended Westside High School in Omaha, Nebraska, where he played on their baseball team and went 9–0 with a 1.29 ERA, 82 strikeouts, and seven walks over 65 innings as a senior in 2015.
[9] On August 31, 2020, the Indians traded Waldron, Mike Clevinger, and Greg Allen to the San Diego Padres in exchange for Austin Hedges, Josh Naylor, Cal Quantrill, Gabriel Arias, Owen Miller, and Joey Cantillo.
[17] On June 23, 2023, the Padres announced they would be promoting Waldron to make his major league debut the next day as the team's starting pitcher.
[19] Waldron was recalled to the majors several times throughout the remainder of the 2023 season, making eight appearances (six starts) going 1–3 with a 4.35 ERA and 31 strikeouts over 41+1⁄3 innings.
[20] Unlike other recent knuckleball pitchers like R. A. Dickey and Tim Wakefield—both of whom relied heavily on throwing knuckleballs—Waldron's primary pitch is a four-seam fastball.