Oswaldo Cabrera was signed by the Yankees as an International free agent July 2, 2015, out of Guatire, Venezuela. He went on to make his professional debut in 2016 in the Dominican Summer League before playing in the Gulf Coast League and Appalachian League.
Cabrera was impressive in his professional debut June 4, going 3-for-4 against the DSL Tigers. The 17-year-old had one double and walked in the game. But he had no such luck in his second game a couple of days later when he held hitless by the same Tigers team. He went on to hit .441/.487/.647 over 19 games in the DSL with five doubles, three triples, and one home run. He drove in 12 runs and walked five times while striking out six times before earning his promotion to the Gulf Coast League.
On July 15, he made his United States debut with the Gulf Coast League Yankees. He had a solid first game, going 2-for-4 with a run scored and a double, driving in a run and walking once. He would spend just seven games in the Gulf Coast League, hitting .455/.471/.818 in 33 at-bats with six doubles and two home runs. He struck out twice, walked once and had six RBIs.
Cabrera earned himself another promotion July 26, when he made his Appalachian League with the Pulaski Yankees. This time his league debut yielded him just one hit in five at-bats. Over 26 total games with Pulaski, he hit .240/.305/.333 in 96 at-bats with four doubles, a triple, and a home run, driving in seven runners and walking eight times.
Overall it was an impressive debut season, as Cabrera hit a combined .345/.396/.523 over three different levels in the minor leagues.
Cabrera opened the 2017 season with the Charleston RiverDogs of the South Atlantic League. With Charleston, he appeared in 49 games where he hit .208/.267/.280. While with Charleston he worked on his versatility, becoming even more familiar with third base while also playing some second base and shortstop.
He we re-assigned to the Staten Island Yankees for the start of the NY-Penn League season. With Staten Island, he hit .289/.337/.344 in 23 games, with most of his playing time coming at second base.
After being promoted to the RiverDogs again on July 21, Cabrera hit .280/.333/.353 in the second half of the SAL season.
Cabrera is a natural shortstop, but like many in the Yankees organization, he has moved all over the infield, playing both second base and third base as well.
Cabrera is very natural in the field, showing off good instincts at second and short. He does not possess any plus tools but has shown he can get the ball without issues. His arm is average, but that could change as he begins to fill his body.
At the plate, he is a switch hitter that has shown he can be productive from both sides. He is patient at the plate, and his pitch recognition is pretty advanced for his age. He has shown some power, having hit four home runs. As he fills into his body, expect to see many of those doubles and triples he hit to turn into home runs.
Cabrera will likely open the 2018 season with the Tampa Yankees of the Florida State League, where he will continue to move around the infield. After making adjustments in Staten Island, he has shown he can replicate the success he had in Pulaski and will be needing to face tougher competition.