Gload grew up in the Long Island community of Springs, New York, where he broke numerous high school and county home run records.

After his record-breaking 1994 season for East Hampton High School, Gload was honored with the "Carl Yastrzemski Award,[1]" which is annually awarded to the most outstanding high school baseball player in Suffolk County by the Suffolk County Baseball Coaches Association.

Perhaps his most memorable high school moment was the Suffolk County Championship game, where he single-handedly propelled East Hampton to the Long Island Championship with a single and three moonshots off of Kings Park High School's left-handed starter Matthew Ligouri.

On July 31, 2000, at the trade deadline, he was dealt to the Chicago Cubs along with minor leaguer Dave Noyce for Henry Rodriguez.

On September 12, 2001, he was claimed on waivers by the Colorado Rockies but did not play in any big league games that season.

He won his first World Series ring with the White Sox in 2005 On December 16, 2006, Gload was traded to the Kansas City Royals for relief pitcher Andrew Sisco.