Toronto Blue Jays Pompey was drafted by the
Toronto Blue Jays in the 16th round of the
2010 MLB 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 (RBI) 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. Splitting time with Bluefield, the
Vancouver Canadians, and the
Lansing Lugnuts, he hit .286 with eight RBI and five stolen bases. 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 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. 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. 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. 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 as he slid into second base during a play and was subsequently placed on the 60-day disabled list by the Blue Jays. He did not make an appearance with Toronto during the 2017 season. On May 4, 2018, Pompey returned to the majors for the first time since 2016 in a game against the
Tampa Bay Rays. On May 12, he was optioned down to the Triple-A
Buffalo Bisons. In a May 29, 2018 game for Buffalo, Pompey suffered a partial tear of the ulnar collateral ligament in his left thumb, sustaining the injury sliding headfirst into third base. He did not appear in the majors again that year as he continued to rehab in the minor leagues. Before a March 21, 2019 spring training game, Pompey was pulled from the lineup after he hit his head on some bats at the top of his locker before the game. Pompey was diagnosed with a concussion and was placed on the injured list. On April 2, Pompey was transferred to the 60-day injured list. On July 23, 2019, Pompey was
designated for assignment. He spent the remainder of the 2019 season in the minors and on November 4, 2019, Pompey elected free agency.
Arizona Diamondbacks Pompey signed a minor league contract with the
Arizona Diamondbacks on February 24, 2020. He did not play in a game for the organization due to the cancellation of the minor league season because of the
COVID-19 pandemic. On May 22, Pompey was released by the Diamondbacks.
Sugar Land Lightning Sloths In July 2020, Pompey signed on to play for the Sugar Land Lightning Sloths of the
Constellation Energy League (a makeshift 4-team independent league created as a result of the
COVID-19 pandemic) for the 2020 season. He played in 4 games for the club, notching only 1 hit in 14 at-bats.
Los Angeles Angels On April 21, 2021, Pompey signed with the
Québec Capitales of the
Frontier League. However, before the beginning of the Frontier League season on May 9, Pompey signed a minor league contract with the
Los Angeles Angels organization. Pompey split time in 2021 with the Double-A
Rocket City Trash Pandas and the Triple-A
Salt Lake Bees, hitting .276 with 5 home runs and 12 RBI. On August 25, Pompey was released by the Angels.
Guelph Royals On March 25, 2022, Pompey signed with the Royals. In 30 games for the team, he batted .381 with five home runs, 22 RBI, and 13 stolen bases. Pompey announced his retirement following the 2022 season in order to pursue a career in emergency services. On July 24, 2024, Pompey came out of retirement and re–signed with the Royals. He became a free agent following the season. ==International career==