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On August 12, 2019, Stewart was named the first Sporting Director of U.S. Soccer.

On June 6, 2018, Stewart was named general manager of the men's U.S. national team.

Stewart accomplished just that when, on October 26, 2015, the Philadelphia Union officially announced that Stewart would take on the role of Sporting Director for the club.

Earnest Stewart was appointed as AZ's Director of Football Affairs in June 2010. The 41-year-old American succeeded Marcel Brands, who left AZ for PSV. Stewart left his post as Technical Director at NAC Breda by mutual consent. Stewart stated in the past that he had a long-term goal of returning to United States soccer in an executive role: "One ambition I do have is to go back to the United States and to be of importance to soccer."

He was named technical director of NAC Breda of the Dutch Eredivisie on May 14, 2006.

Stewart became the eighth U.S. man to make his 100th international appearance in a 2004 World Cup qualifier against Grenada. His 111 goals as a professional in the Netherlands makes him the highest-scoring American in international club play. He was named U.S. Soccer Athlete of the Year in 2001.

In January 2003, he left the Netherlands to play in Major League Soccer, and was allocated to D.C. United, where he won the MLS Cup in his second season. His scoring numbers did not equal his earlier high standards, as he tallied just four regular season goals and one playoff goal in MLS. He left D.C. after the 2004 season, coming back to the Netherlands and his original club, VVV-Venlo, where he became technical director following his retirement in 2005.

By 1996, Stewart had moved to NAC Breda, eventually spending more than six seasons at NAC. The club was relegated in 1999, but Stewart helped the club win the First Division in 2000, thereby earning promotion back to the Eredivisie. During his years at NAC, he also played in all of the U.S. team's matches at the 1998 and 2002 FIFA World Cups, becoming one of only five U.S. men to play in three World Cups.

In his first season at Willem II, he finished third on the goal-scoring list for the Dutch First Division, with 17. He went on to score 49 goals in six seasons there. In the meantime, he developed into a regular for the U.S. national team, starting all four games that the U.S. played in the 1994 FIFA World Cup. Most notably, he scored the goal that gave the U.S. its winning margin against Colombia in group play, the first World Cup game won by the U.S. since 1950.

Stewart, the son of an African American U.S. Air Force airman Earnie Stewart, and his Dutch wife Annemien Stewart, grew up in the Netherlands, and began his professional career in that country in 1988 with VVV. He spent two years at the Dutch First Division (second-level) club before moving to Eredivisie side Willem II in 1990. By the end of 1990, he made his first appearance for the U.S. national team against Portugal.

Earnest "Earnie" Stewart (born March 28, 1969) is an American retired soccer player who was a regular midfielder for the U.S. national team from 1990s until his retirement in 2005. He is currently the sporting director of the United States Soccer Federation.