He played in Major League Baseball (MLB) for the Florida Marlins, Washington Nationals, Oakland Athletics, Minnesota Twins, and Kansas City Royals.

Willingham saw a reduced amount of playing time in 2008 due to a 50-game stint on the disabled list, appearing in just over 100 games as opposed to over 140 in the previous two years.

On November 11, 2008, Willingham was traded to the Washington Nationals, along with pitcher Scott Olsen for Emilio Bonifacio, Jake Smolinski, and P.J.

Willingham began 2009 as the Nationals' fifth outfielder behind Adam Dunn, Elijah Dukes, Austin Kearns, and Lastings Milledge.

Dunn was eventually moved to first base and Milledge was traded for then-Pittsburgh Pirates outfielder Nyjer Morgan.

On December 16, 2010, Willingham was traded to the Oakland Athletics for pitcher Henry Rodríguez and outfielder Corey Brown.

[3] His 2011 batting average of .246 was his lowest since his rookie season, but he reached career pinnacles in home runs (29) and RBIs (98).

[11] He hit a bloop single in the 2014 American League Wild Card Game and was taken out for pinch runner Jarrod Dyson.

Josh and Ginger started a charitable foundation and fundraising golf tournament named in honor of his younger brother, Jon Willingham, who died in a car accident in 2009.