After completing his sophomore season with the Golden Gophers, Leopold became the property of the Calgary Flames, traded by the Mighty Ducks in exchange for Andrei Nazarov and a second-round draft pick.

In his second season, Leopold would play in all 82 regular season games, scoring 33 points as well as contributing to the Flames' playoff run to the 2004 Stanley Cup Finals, play which earned him a spot in the defense of the American national team for the 2005 World Championships as well as for the 2006 Winter Olympics.

[6] Just a month later, Leopold was injured again, fracturing his wrist on February 17, 2007, effectively missing the rest of the season, and playing in just 15 games.

[17] Leopold later returned to the Pens' lineup for Game 2 of the Eastern Conference Semi-final matchup against the Montreal Canadiens.

On July 1, 2010, Leopold left the Penguins as a free agent and signed a three-year contract with the Buffalo Sabres.

[20] Leopold played 18 games with the Blue Jackets, registering one goal and two assists, before he joined his third team in the year when he was dealt to the Minnesota Wild in exchange for Justin Falk and a fifth-round pick in 2015 on March 2, 2015.

[22] Leopold's trade to the Minnesota Wild, marking a return to his home state, gained the attention of media outlets after it was revealed that one of his daughters wrote a letter to the Minnesota Wild coaching staff asking for them to trade for Jordan to be closer to family.