Gallery played college football at the University of Iowa before being selected with the second overall pick in the 2004 NFL Draft.
Robert Gallery attended East Buchanan High School in Winthrop, Iowa and starred in football, basketball, and track. In football, Gallery played tight end and linebacker positions in high school, and he also handled punting and kickoff duties. He was an all-conference honorable mention selection as a sophomore before being named first team all-conference as a junior and senior. Gallery helped his high school team to a three-year record of 24-8, including a 19-2 record in district play. He was a Des Moines Register Class 1A All-State first team selection as a senior.
Robert Gallery went to the University of Iowa, where his older brother, Nick Gallery, was an All-Big Ten punter. His younger brother, John Gallery, later also became a punter at Iowa. After redshirting in 1999, Gallery had three catches for 52 yards as a starting tight end as a freshman in 2000 before moving to the tackle position. He started six games at right tackle as a freshman.
As a sophomore, Gallery started every game at left tackle and made vast improvements throughout the year. He helped Iowa lead the Big Ten Conference in scoring in 2001 as Iowa qualified for their first bowl game in four years. As a junior in 2002, Gallery started all 13 games at left tackle and was a first team All-Big Ten selection. He helped lead Iowa to their first Big Ten title in 12 years and their first undefeated conference season in eighty years. He also won the team's Hustle Award.
In 2003, Robert Gallery led Iowa to another ten win season and was voted as Iowa's co-captain and co-MVP for the season. He was a first team All-Big Ten selection for the second straight year and named the Big Ten Conference Offensive Lineman of the Year.
Gallery was a consensus first team All-American in 2003. He was also awarded the 2003 Outland Trophy. He was also a three-time academic All-Big Ten selection at Iowa.
Robert Gallery was selected with the second overall pick in the 2004 NFL Draft by the Oakland Raiders, with a perfect 9.0 Draft Prospect Rating, the highest for any offensive lineman. In 2004, he started 15 games at right tackle and gave up 3 Sacks. In 2005, he started all 16 games at right tackle and gave up 3.5 Sacks. The Raiders moved him to left tackle at the beginning of the 2006 preseason. In the Raiders' first game of the 2006 regular season, Gallery was part of an offensive line that gave up nine sacks (at least 3 charged to him) to the San Diego Chargers. He played 10 games on the season, and gave up 10.5 Sacks on the season, placing him 4th in most sacks given up, despite missing 6 games. His main problem in pass protection is his inability to effectively hand punch. He has also not benefited from the revolving door of offensive line coaches he has faced in his young pro career. In 2007, Oakland coaches have stated that Gallery is going back to right tackle, where he was somewhat dominant early in his career. Up to this point in his profession he is considered a draft bust along the lines of Fellow over hyped Big 10 Left Tackle prospect Tony Mandarich. Also during the 2007 OTAs new coach Lane Kiffin said that Gallery was participating with a "nasty demeanor" and had been successful getting "guys on the ground."
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