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," which is annually awarded to the most outstanding high school baseball player in Suffolk County by the Suffolk County Baseball Coaches Association. His 41 career home runs, and 20 in the 1994 season alone, are New York state high school records. 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 four moonshots off of Kings Park High School's left-handed starter Matthew Ligouri. Gload attended the University of South Florida, where he played under longtime Coach Eddie Cardieri. In 1995 and 1996, he played collegiate summer baseball with the Hyannis Mets of the Cape Cod Baseball League.
In January, Gload was involved in two deals with the New York Mets in a span of six days, first moving to the Mets in a three-team, 11-player trade, then having his contract purchased by Colorado from the Mets. Gload batted.258 with a home run and four RBIs in limited action with the Rockies.
Just before the season, Gload moved on to the Chicago White Sox organization, being acquired by Chicago for minor leaguer Wade Parrish. Gload did not appear in a Major League uniform in 2003, but in and again in, he saw significant duty with the White Sox. He batted.321 in 2004 with seven homers and 44 RBIs, finishing seventh in the American League Rookie of the Year voting. In 2006, his numbers were.327 with three homers and 18 RBIs in fewer at-bats. 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. In, with Kansas City, Gload logged career highs in at-bats and RBIs, being used as a starter more than in the past. He batted.288 with seven homers and 51 RBIs in 102 games. During the 2007–2008 offseason, Gload signed a two-year Major League contract with Kansas City.
On December 15, 2009, Gload signed a 2-year, $2.6 million contract with the Philadelphia Phillies. In 2012, Gload's contract with the Phillies expired, making him a free agent.
