The Minnesota Timberwolves selected Szczerbiak 6th overall in the 1999 NBA draft. His best year as a pro was in 2002, when he was a coaches' selection to the Western Conference All-Star team. Later he tied a Timberwolves franchise record of 44 points on April 13, 2003, since broken by Kevin Love, Corey Brewer, Andrew Wiggins, Karl-Anthony Towns, Mo Williams, and Derrick Rose. Szczerbiak was coming off the bench for the 2004–05 NBA season. He was uncomfortable with the role and wanted to be a starter. In the 2005–06 season, the former All-Star returned to the starting role.