Wilkerman Garcia signed with the New York Yankees for $1.35 million as an international free agent July 2, 2014, out of Maracay, Venezuela, by Esteban Castillo. He was ranked by Baseball America as the 7th top prospect in the entire 2014 international signing period.
Garcia made is professional debut for one the Yankees Dominican Summer League (DSL) (Rookie) teams. He quickly earned a promotion to the United States after showing a strong performance in the DSL. Garcia made his stateside debut by playing for one of the organizations two Gulf Coast League (Rookie) teams. In a combined 39 games, Garcia hit .299 (28-127) with six doubles, a triple, 19 runs batted in, 23 runs scored, and 11 stolen bases. He reached base in an astonishing 35 games, earning a .414 on-base percentage. Following the season, Baseball America ranked Garcia as the number six prospect in the Gulf Coast League.
Following a strong first season, 2016 was nothing shot of a disaster for the highly-touted prospect. Wilkerman spent the entire season with the Pulaski Yankees (Rookie) and slashed a miserable .198/.255/.284 at the plate. In 54 games, Garcia drove in 13 runs and collected a total of 44 hits in 22 at-bats. He also committed 14 errors at short in 233 total chances, giving him a .940 fielding percentage.
Even after a lousy season, Wilkerman was once again promoted. This time the youngster made his Single-A debut for the Staten Island Yankees (Single-A – Short Season). He performed slightly better than his prior season, hitting .222 at the plate and earned a .929 fielding percentage at shortstop. His strength has not advanced as scouts had projected a couple of years ago as he collected just 10 doubles, three triples, and one home run, leading to a very pedestrian .552 OPS. Another concern for Garcia was his strikeout numbers increased, while is walk rate decreased.