Toronto Blue Jays
Hill was Toronto's first draft pick (13th overall) in the 2003 MLB draft, and he made his major league debut on May 20, 2005, against the Washington Nationals, after being called up from the minor leagues a day earlier as an injury replacement for Corey Koskie. Hill would finish the game 2-for-4, and he recorded an RBI triple off Nationals pitcher Claudio Vargas for his first career hit as the Blue Jays won, 6–1. Although he was brought up as a shortstop, Hill appeared as a third baseman, a designated hitter, and as a second baseman during the course of the season. He finished the 2005 season with a .274 batting average, .348 OBP, and 25 doubles in 361 at-bats. After the trade of Orlando Hudson to the Arizona Diamondbacks, Hill became the starting second baseman for the Blue Jays in 2006, but was moved back to shortstop mid-season after the demotion of Russ Adams. After experiencing defensive struggles at shortstop, he was then moved back to second base, with John McDonald taking over at shortstop.
On May 29, 2007, in a game at home against the New York Yankees with Andy Pettitte pitching, Hill became only the second player in Blue Jays history to accomplish a "straight steal" of home.
Hill won a Fielding Bible Award at second base for his fielding excellence in 2007.
On April 4, 2008, Hill agreed to a four-year, $12 million deal that included a club option that could have run through the 2014 season. The contract would have been worth as much as $38 million if Toronto kept Hill in the fold for all seven years of the deal.
On May 29, Hill suffered a Grade II concussion in a collision with teammate David Eckstein during a game against the Oakland Athletics. Hill missed the remainder of the season.
Hill returned from his concussion during spring training. On July 5, 2009, Hill was selected by managers and players to take part in the All-Star Game in St. Louis. Hill finished the 2009 season with 37 doubles, 36 home runs, 108 runs batted in, and a batting average of .286 in 158 games. After the season, Hill received the AL Comeback Player of the Year Award. He was voted the Blue Jays Player of the Year. He was also honored with his second Fielding Bible Award.
Prior to the first game of the 2011 season, the Blue Jays announced that they had declined the three option years on Hill's contract. Hill was placed on the 15-day disabled list on April 24, retroactive to April 20, with a strained hamstring.