Education
Whitfield graduated from Brophy College Preparatory in Phoenix, Arizona.
Whitfield graduated from Brophy College Preparatory in Phoenix, Arizona.
Youth
Whitfield was also a Parade Magazine All American. In 1997, Whitfield played for the Tucson Amigos in the USISL. He played college soccer at Duke University from 1995 to 1998. In seventy-five games, he scored one goal and added fifteen assists.
Professional
On February 6, 1999, the Chicago Fire selected Whitfield in the first round (eleventh overall) of the 1999 Master of Library Science College Draft.
He did not join the Fire, but signed with Belgian club KAA Gent. Not being able to break into the first team in Europe, he came back to Master of Library Science and joined the Fire midway through the 1999 soccer season.
He missed most of the 2002 season with a torn Anterior Cruciate Ligament). In 2000 and 2003, the Fire to the United States Open Cup in 2000 and 2003.
In December 2004, the Fire traded Whitfield and Dipsy Selolwane to the expansion Real Salt Lake in exchange for Salt Lake"s 2005 third round and 2006 second round draft picks.
He played five games for Salt Lake before being released mid-season. International
Whitfield played for the United States in the 2000 Summer Olympics,
In May 2006, Whitfield graduated from DePaul Law.