Drafted as the 11th overall pick in the first round of the 2005 MLB draft by the Pittsburgh Pirates, Andrew McCutchen signed with the team for a $1.9 million bonus, quickly advancing through the minor leagues. He earned SAL Mid-Season and Post-Season All-Star selections in 2006, followed by the Pirates’ Minor League Player of the Year award. His minor league career also included appearances in the AFL Rising Stars (2007) and Futures Game (2008), leading to his MLB debut with the Pittsburgh Pirates on June 4, 2009. In his debut season, McCutchen hit his first MLB career home run, recorded his first walk-off hit, and notably hit three home runs in a single game, earning him the Baseball America Rookie of the Year award.
His 2019 season was cut short by a torn ACL. In 2022, he signed a one-year contract with the Milwaukee Brewers, during which he achieved his 1,000th career RBI. McCutchen made a highly anticipated return to the Pittsburgh Pirates in 2023, signing a one-year, $5 million contract, and notably recorded his 2,000th career hit. He subsequently signed another one-year, $5 million contract to remain with the Pirates for the 2024 season, where he hit his 300th career home run.
As of 2025, McCutchen reached his 240th home run, tying Roberto Clemente on the Pirates’ all-time HR list, and then surpassed him with his 241st home run. He also recorded his 2,200th career hit and achieved the remarkable feat of hitting at least ten home runs in each of his first 17 seasons.