Pompey was drafted by the Toronto Blue Jays in the 16th round of the 2010 Major League Baseball draft out of John Fraser Secondary School in Mississauga, Ontario. He made his professional debut for the Gulf Coast League Blue Jays that season, hitting.191 with two home runs and five runs batted in in 11 games. Pompey spent 2011 with the Gulf Coast League Blue Jays and Bluefield Blue Jays. Overall, he played in 60 games and hit.239 with five home runs, 17 RBI, and 23 stolen bases. Pompey played in only 20 games in 2012 due to a broken left hand. Splitting time with Bluefield, the Vancouver Canadians, and the Lansing Lugnuts, he hit.286 with eight RBI and five stolen bases. He returned to Lansing in 2013 to play in 115 games, and finished the year batting.261 with six home runs, 40 RBI, and 38 stolen bases. After the season, he was awarded a minor league Gold Glove Award, playing the full season without recording an error. Pompey started the 2014 season with the Dunedin Blue Jays, and was named to the 2014 All-Star Futures Game on June 24, 2014. Up to his selection to the team, he had posted a.313/.392/.460 triple-slash line in 67 games, along with six home runs and 27 stolen bases. Pompey was promoted to the Double-A New Hampshire Fisher Cats on June 27, 2014, and to the Triple-A Buffalo Bisons on August 20. On August 26, the Blue Jays organization announced that Pompey would play for the Mesa Solar Sox of the Arizona Fall League at the completion of the 2014 season. He finished the 2014 minor league season with a.313 batting average, nine home runs, 52 RBI, and 43 stolen bases in 112 games played. On September 3, Pompey was named to Baseball America's Second Team All-Stars for 2014.
Toronto Blue Jays
On September 1, 2014, Pompey was announced as one of the Blue Jays' September call-ups. He made his MLB debut against the Tampa Bay Rays on September 2 as a pinch-runner for Edwin Encarnación. After three additional appearances as a pinch-runner, Pompey had his first at-bat on September 10 against the Chicago Cubs and earned an RBI on a groundout to first base. On September 19, Pompey recorded his first Major League hit, a single to right-field against New York Yankees starting pitcher Hiroki Kuroda. Three days later he earned his first MLB multi-hit game and run in a 14–4 win over the Seattle Mariners. Pompey would hit his first career home run, a solo shot to right field, off Mariners ace Félix Hernández the following day. Playing against the Baltimore Orioles on September 26, Pompey had the best game of his young career, posting two runs scored and two RBI by hitting his first double and two triples, finishing the night 3–4. He became the third Blue Jays rookie to record two triples in one game, and first since Alex Ríos in 2005. Prior to the start of the 2015 season, MLB named Pompey the number two prospect in the Blue Jays' organization, the 7th best outfield prospect in baseball, and the 43rd overall prospect on their top 100 list. Pompey opened the 2015 season as the starting centre fielder for the Blue Jays. He struggled to open the season, batting just.193 through 23 games, and on May 2 he was optioned back to Triple-A Buffalo. After continuing to struggle at the Triple-A level, Pompey was sent down to Double-A New Hampshire on June 6. On September 1, Pompey was called up by the Blue Jays. He appeared in 34 games for the Blue Jays in the 2015 regular season, and batted.223 with two home runs, six RBI, and five stolen bases. Pompey was on the Blue Jays postseason roster, appearing mostly as a pinch runner. In five postseason games, he recorded a single in his lone at-bat, as well as four stolen bases. Pompey attended 2016 Major League spring training, and was optioned to minor league camp on March 18. He played with the Buffalo Bisons until September 1, when he was called up by the Blue Jays. Pompey played in eight games for the Blue Jays in 2016, mostly as a pinch runner. He scored three runs and stole two bases. He was added to the Wild Card roster but did not play in the game. Pompey was not on the Division Series roster, but was added to the Championship Series roster on October 14. During the 2017 World Baseball Classic, Pompey suffered a concussion and was subsequently placed on the 60-day disabled list by the Toronto Blue Jays. He did not make an appearance with Toronto during the 2017 season. On July 23, 2019, Pompey was designated for assignment. He became a free agent following the 2019 season.
Pompey's parents are Ken and Valerie Pompey, who taught him to switch-hit at age 3. He has a brother, Tristan, and a sister, Kayla. Tristan is also a professional baseball player.
