Pittsburgh Pirates in 2013 The
Pittsburgh Pirates selected Dickerson in the third round of the
2011 Major League Baseball draft. After signing for a
signing bonus of $380,700, Dickerson spent most of the rest of the 2011 season with the
State College Spikes, batting .313/.393/.493 with an .886 OPS (9th in the
New York-Pennsylvania League) in 150 at bats; his 16 doubles were second among all short-season batters. Dickerson spent the 2012 season with the
Bradenton Marauders, where he batted .295/.353/.451 with 31 doubles (4th in the league), 13 home runs (7th), and 90 RBIs (2nd) in 488 at bats and was named the
Florida State League Player of the Year, a post-season All Star, and an MiLB organization All Star. Prior to the 2013 season, Dickerson was named the 7th-best first base prospect in baseball by
MLB.com. He spent 2013 with the Double-A
Altoona Curve, where he moved from first base to the outfield. He batted .288/.337/.494 with 36 doubles (2nd in the league), 17 home runs, and 68 RBIs in 451 at bats and was named the
Eastern League Rookie of the Year, a post-season All Star, and an MiLB organization All Star.
San Diego Padres On November 25, 2013, the Pirates traded Dickerson to the
San Diego Padres for
Jaff Decker and
Miles Mikolas. Dickerson sprained his left ankle in 2014 spring training with the Padres when he stepped on a sprinkler head, and an
MRI later found a bone
cyst in his left heel which required surgery and a
bone graft. The surgery delayed his start to the 2014 season, but he finished with 34 games with the Double-A
San Antonio Missions, batting .321/.367/.496 in 137 at bats. On November 20, 2014, the Padres added Dickerson to their
40-man roster to protect him from the
Rule 5 draft. Dickerson spent most of 2015 with the
Triple-A El Paso Chihuahuas, hitting .307 (10th in the league)/.374/.503 with 82 runs (3rd), 36 doubles (6th), 9 triples (2nd), 12 home runs, and 71 RBIs in 459 at bats over 125 games, including 88 starts in left field. His performance earned him the
Pacific Coast League Rookie of the Year Award, and he was named a post-season All Star and an MiLB organization All Star. On August 6, 2015, Dickerson made his Major League debut with the San Diego Padres with a pinch-hitting appearance in the 8th inning. He was called up to replace
Will Venable, who went on paternity leave. The next day, Dickerson collected his first Major League hit with a pinch single in extra innings. Dickerson returned to the Padres when rosters expanded in September. A tweaked
hip flexor limited his playing opportunities, but Dickerson appeared in eight more games as a pinch hitter, and once as a defensive substitute in left field. Dickerson started the 2016 season in Triple-A El Paso. On May 2, the Padres recalled Dickerson from Triple-A. On May 10 against the
Chicago Cubs at
Wrigley Field, Dickerson hit a pinch-hit
grand slam off of
Adam Warren for his first career home run and his first four career RBIs. He made his first Major League start in left field the following day, but was returned to El Paso on May 14. With the Chihuahuas, he continued a 28-game minor league hitting streak through the end of May. On June 28, Dickerson was recalled from El Paso when
Jon Jay broke his forearm. Dickerson remained as the regular left fielder for the Padres for the remainder of the season. For the season, with El Paso he batted .382/.425/.622 with 10 home runs and 51 RBIs in 217 at bats. In spring training of 2018, while trying to come back from his back surgery, Dickerson tore his
UCL in his elbow and underwent
Tommy John surgery, costing him another full season. He was outrighted off the roster after the season. He elected free agency on November 3, 2018, and later re-signed to a minor league deal on December 11. Playing for AAA El Paso in 2019, he hit .372/.469/.606 with 5 home runs and 20 RBIs in 94 at bats. Dickerson had his contract selected to the major leagues on May 3, 2019, but after 19 at bats with the Padres was designated for assignment on June 5. With the Giants in 2019, he batted .290/.351/.529 with 28 runs, 6 home runs, and 26 RBIs in 155 at bats. In 2020 he batted .298/.371/.576 with 28 runs, 10 home runs, and 27 RBIs in 151 at bats. He played 41 games in left field, and 5 games in right field. Avoiding arbitration, Dickerson and the Giants agreed on a $2.1 million salary for the 2021 season. During the season, he was on the injured list three times, with right shoulder, upper back, and right hamstring issues. In the 2021 regular season, he batted .233/.304/.420 with a career-high 13 home runs and 38 RBIs in 283 at bats. On November 26, 2021, he was placed on unconditional release waivers. The Braves designated Dickerson for assignment on April 28. Two days later, Dickerson was outrighted to the
Gwinnett Stripers, for whom he batted .239/.305/.426 with 12 home runs and 43 RBIs in 322 at bats, playing 40 games in right field and 20 games in left field. He had four hits in 43 at bats for the Braves. In 12 games, he batted .261/.333/.370 with 12 hits and five RBI. Dickerson was released by Monclova on May 5. In 115 games for the Ducks, Dickerson hit .314/.389/.576 with career–highs in home runs (26) and RBI (91).
Chunichi Dragons On December 22, 2023, Dickerson signed with the
Chunichi Dragons of
Nippon Professional Baseball. In 32 games for Chunichi in 2024, slashing .205/.314/.352 with three home runs and five RBI. On October 26, 2024, the Dragons announced they would not bring Dickerson back for the 2025 season, making him a free agent.
High Point Rockers On June 18, 2025, Dickerson signed with the
High Point Rockers of the
Atlantic League of Professional Baseball. In 78 games he hit .265/.367/.514 with 19 home runs, 68 RBIs and 2 stolen bases. ==Team Israel; World Baseball Classic==