Jimmy started playing hockey at the age of three in the Ogdensburg Minor Hockey Association. He did not start playing goalie until he was seven years old. He played junior hockey in Ontario. 

Jimmy participated in the New York Player Development camps and festivals which led him to the U.S. National Under-17 and Under-18 teams. For his play with the National Teams, he received the Dave Peterson Goalie of the Year Award in 2002. Howard represented the United States internationally on the World Junior U18 team, the World Junior team, two Men’s World Championships and one Olympic Team.

Howard attended the University of Maine. During his time there he set school records for single season and career in shutouts, goals against average and save percentage. Jimmy still holds the NCAA single season save percentage record.

Jimmy was selected on the Hockey East All-Rookie Team, Rookie of the Year, First All-Star Team, All-Tournament Team and Tournament MVP as well as Hockey East Goaltender of the Year during his time at UMaine.

The Detroit Red Wings drafted Jimmy in the second round of the 2003 NHL Entry Draft. Jimmy would spend his entire professional career with the Detroit Organization. In 2010 Howard was a finalist for the Calder Memorial Trophy as the NHL’s top rookie. Over his fifteen-year professional career Jimmy played 813 games, 591 with the Detroit Red Wings in the NHL. He was the eighth American-born goalie to win 200 games. During his career he was selected as an All-Star three times in the National Hockey league and one in the American Hockey League.