Stern is the second Jewish player from Canada in major league history (following Goody Rosen). He, Kevin Youkilis, and Gabe Kapler set a record for most Jewish players on a team at once since the expansion era.
Stern played for the London Badgers Baseball Club in London, Ontario from the age of 16 to the age of 18.
Stern played three years on a baseball scholarship at the University of Nebraska, from which he graduated with a Sociology degree. He hit .356 as a sophomore in 2000 to earn 2nd-Team All-Big 12 honors. After the 2000 season, he played collegiate summer baseball with the Harwich Mariners of the Cape Cod Baseball League. In 2001, he appeared in the College World Series, and was named First-Team Academic All-Big 12, as well as an All-Big 12 Honorable Mention, after hitting .292 with 68 runs and 27 stolen bases in 64 games.
Stern was drafted twice: first, by the Toronto Blue Jays in the 22nd round (651st overall) of the 1998 MLB draft, and then by the Atlanta Braves in the 3rd round (105th overall) of the 2001 MLB draft, before moving to the Boston Red Sox in 2004 as a Rule 5 draft pick.
In 2004, while playing for the Greenville Braves, Stern started in left field for the Southern League‘s Eastern Division All-Star team, and was named an outfielder on the league’s year-end All-Star club. He hit .322 with 64 runs, 26 doubles, and 27 stolen bases in 102 games. He ranked 3rd in the league in hitting, 8th with a .378 on-base percentage, and 9th with a .480 slugging percentage. His 27 steals were 3rd-most in the Braves system, and he had 41 multi-hit games in 99 starts. He was named Atlanta’s Double-A Player of the Year. Stern missed 26 games to play for Team Canada at the 2004 Summer Olympics in Athens, where he hit .250 (8-for-32) with 4 RBIs and 9 runs in 9 games.
The Boston Red Sox made Stern a Rule 5 draft selection from the Braves in 2004. In 2005, he batted .321 (26-for-81) with 8 doubles, 14 RBIs, and 3 steals during a pair of rehab stints with Pawtucket, including a 21-game hitting streak.
In 2009, while playing for the Huntsville Stars, as of July 9 Stern was second in the Southern League in steals (27), runs (58), and triples (6), and third in hits (95). Stern was selected to be a starting right fielder for the Southern League North Division All Star team, with the game to be played July 14 in Birmingham. Promoted to Nashville, he batted .310.