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In 2014, Wilkerson agreed to manage a middle school baseball team at The King's Academy in West Palm Beach, Florida, leading the team to a league championship in his first year. After the season, Wilkerson was hired as the school's varsity baseball coach.

Wilkerson is also a coach for USA Baseball. In 2014, he was named Volunteer Coach of the Year by the organization.

While coming up through the minors, Wilkerson was a member of the gold medal-winning USA baseball team in the Sydney Olympics. In one of the biggest upsets in Olympic history, Team USA defeated Cuba 4–0 in the Gold Medal Game.

Wilkerson was inducted into the University of Florida Athletic Hall of Fame as a "Gator Great" in 2010, and the National College Baseball Hall of Fame in 2012. In 2014, he received his bachelor's degree in sport management from the University of Florida.

On February 23, 2010, Wilkerson attempted a brief comeback by agreeing to a minor league contract with the Philadelphia Phillies. However, he was released on March 29.

On February 16, 2009, Wilkerson signed a minor league contract with an invitation to spring training with the Boston Red Sox.

Wilkerson decided to retire in 2009, having had one hit in nine Triple-A at-bats in the Boston minor league affiliate. He retired with a .247 batting average, .350 on-base percentage and 122 career home runs.

On January 31, 2008, Wilkerson signed a one-year contract with the Seattle Mariners. On April 30, he was designated for assignment, and on May 8 was given his unconditional release. May 9, he signed with the Toronto Blue Jays. On August 22, he was put on the 15-day disabled list by the Toronto Blue Jays . On October 30, 2008, Wilkerson filed for free-agency from Toronto.

While playing for the Texas Rangers in 2007, Wilkerson hit three home runs in one game – the third player to do so in 2007 behind Alfonso Soriano and Carlos Lee. An injury to, and later the trade of, Mark Teixeira led to Wilkerson making many of his starts at first base in 2007.

Wilkerson married Dana Marie Gleason in 2006. They have three children—Ella, Ava and Max. In 2006, he was named a Kentucky Colonel by Governor Ernie Fletcher, the highest honor of the Commonwealth of Kentucky.

Wilkerson opened the 2005 season as the regular center fielder and leadoff hitter after the Expos moved to Washington and became the Nationals. On December 7, 2005, Wilkerson was traded to the Texas Rangers along with outfielder Terrmel Sledge and minor league pitching prospect Armando Galarraga for second baseman Alfonso Soriano. He hit for the cycle for the second time on April 6, 2005, against Philadelphia (with the Nationals, in their second game after moving from Montreal). Wilkerson also hit the first grand slam home run hit by a Washington Nationals player.

In 2004, he hit the last home run in Montreal Expos franchise history.

He appeared once more in a Montreal Expos uniform during the Major League Baseball Japan All-Star Series shortly after the 2004 regular season. The Expos were to become the Washington Nationals for the 2005 season, prompting some to refer to Wilkerson as "The Last Expo."

From 2002–2003, Wilkerson delivered almost identical seasons with a .266 average, 20 home runs and 59 RBI in (2002), and .268, 19, 77 in (2003). In 2002, he hit 20 home runs, an Expos rookie record and was named Rookie of the Year by The Sporting News. His most productive season came in (2004), when he posted career-highs in homers (32), hits (146), doubles (39), runs (112), walks (106), slugging percentage (.498) and OPS (.872), and hitting .255 with 67 RBI. He hit for the cycle on June 24, 2003, against Pittsburgh (with the Expos). In that first instance, Wilkerson became the first player since 1957 to have the minimum four plate appearances and hit for a natural cycle.

Wilkerson debuted with Montreal on July 12, 2001, appearing in 38 games in left field.

He recorded his first major league hit off Tim Wakefield of the Boston Red Sox on July 17, 2001 and his first major league home run off Atlanta Braves pitcher Jason Marquis on July 26, 2001.

As a junior in 1998, he became the first player in college history to hit 20 home runs, steal 20 bases, and win 10 games as a pitcher in the same year. The Gators advanced to the 1998 College World Series, and he was awarded the Rotary Smith Award as the most outstanding player in college baseball.

A line drive hitter and versatile defensive player, Wilkerson received an athletic scholarship to attend the University of Florida in Gainesville, Florida, where he played for coach Andy Lopez's Florida Gators baseball team from 1996 to 1998. A three-time first-team All-American, Wilkerson led the Gators to the College World Series in 1996 and 1998 with both his hitting and pitching. In the 1996 College World Series, he hit a dramatic grand slam to defeat the rival Florida State Seminoles.

Wilkerson was born in Owensboro, Kentucky, where he attended and played baseball at Apollo High School. Wilkerson played for the US national junior baseball team in 1995. He was the most valuable player (MVP) of the World Junior Baseball Championship, pitching a three-hit shutout against Taiwan in the gold medal game, hitting .360, and leading Team USA with three home runs and eight runs batted in (RBI) for the tournament.

Stephen Bradley Wilkerson (born June 1, 1977) is an American former professional baseball outfielder and first baseman in Major League Baseball for eight seasons. Wilkerson played college baseball for the University of Florida, and was selected by the Montreal Expos in the first round of the 1998 Major League Baseball Draft. During his Major League career, he played for the Expos, Washington Nationals, Boston Red Sox, Texas Rangers, Seattle Mariners, and Toronto Blue Jays.