The Yankees were protective of Whitlock after the 2021 draft, but he had a breakout season last year, advancing to the major leagues. He had a 1.96 ERA and struck out 27.2 percent of batters over 38.2 innings during the regular season. Then, Whitlock blew out his elbow at Double-A Trenton and underwent Tommy John surgery. After that, Whitlock struggled mightily in his first two seasons with the Red Sox.