Thoughts on Oswaldo Cabrera

By Andrew Hefner

May 19, 2025

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On March 1st, 2025, I wrote an article about how the Yankees needed Oswaldo Cabrera on the opening day roster despite fans' pleas to make a trade or sign a new third baseman. Cabrera was always the right choice, as his passion, energy, exceptional defense (at any position), and keen ability to hit in the clutch, led me to opine that there is no one better.

In the same article, I mentioned in my summary that, "Oswaldo Cabrera embodies the Yankees' spirit. He takes time for the fans, he knows what it means to wear the pinstripes and the significance they carry, and, throughout his career, he has put in the work and effort to get to where he is today.”

Obviously, those sentiments are evident to the Yankees' universe. When Cabrera went down with a grueling injury last week, the collective fandom was able to unite to cheer on a player who went from being an unranked and unknown prospect to one of the most popular on the team.

Pre-Covid Era

Oswaldo Cabrera grew up in Venezuela and trained with former Tigers and Mariners infielder Carlos Guillén at his academy. Cabrera is the son of a former professional volleyball player and has two brothers who both grew up playing baseball.

At just 16 years old, the Yankees signed Cabrera as an international free agent. This makes him the second-longest tenured Yankee (behind Aaron Judge). Cabrera has been with the organization since July 2015.

Oswaldo Cabrera began his professional journey a year later with the Dominican Summer League Yankees and the Florida Complex League Yankees, and was named to the Dominican Summer League American League All-Star Team in 2016. He finished the short season with the Yankees' Rookie Ball team in Pulaski.

The following season, Cabrera made his long-season MiLB debut with the Charleston Riverdogs, the former Single-A affiliate of the Yankees, and current Blue Jays affiliate. In 2017, he slashed a .242 average with the Riverdogs, but was moved down to Class-A Staten Island, where he shined, batting .289 over 23 games to round out the season.

Back in Charleston for 2018, Cabrera struggled more, lowering his average to just .229, however, his power started to appear with 6 home runs and 48 RBIs during the season.

Despite the down season, he made his way to A+ with the Tampa Tarpons in 2019, where he improved his average to .260, but was still fighting to find his footing in the minor league system. After the 2020 lockdown, however, Cabrera emerged as a completely new player, and his stock within the organization he had already been with for 5 years began to rise.

Post Covid

Much of Cabrera's early success came with the newly named AA affiliate of the Yankees, the Somerset Patriots. Starting as a second baseman in 2021, Cabrera’s power was on full display as he mashed 24 home runs in 109 games with a slugging percentage of .492. He was named to the mid-season Northeast AA All-Star team, won the Eastern League MVP, and made a jump from being unranked, all the way to being the 16th-ranked prospect in the Yankees' organization. His surge in production quickly put him firmly on a fast track to the majors, and soon, Cabrera was given the call during that strong 2021 season to make his way to AAA.

In 2022, his final real season in the minors, Cabrera shined once again in 47 games with the AAA Railriders; however suffered a shoulder injury that placed him on the injured list. He came back stronger than ever, though, as by early August the Yankees, riddled by injuries, called up Cabrera to make his Major League Debut just a month following his return from injury.  

In the majors in 2022, Cabrera played in 44 games, batting .247, with 6 home runs and 19 RBIs. He finished the season with the big league squad.

In 2023, Cabrera got off to a slow start, and as more players came back from injuries, the Yankees optioned him to AAA for just 10 games in June, before he made his return to the Majors soon after. He did struggle throughout the season, but still proved helpful as his versatility allowed manager Aaron Boone to play him at almost any position. As of 2025, there are only five active players who have played every position except catcher in an MLB game, and Cabrera is one of them.

In 2024, Cabrera got off to a hot start as he began the season starting almost every game at multiple positions. He had a major uptick in his stats as he improved his average to .247. Again, he was utilized at many positions and was an extremely helpful tool for the Yankees to have as they made their run to the World Series.

In 2025, Cabrera was once again off to a strong start; however, just last week, a gruesome injury came when he was sliding home on a sacrifice fly from Aaron Judge. Cabrera suffered a broken ankle and underwent surgery early this week, and while expected to make a full recovery, doctors estimate that it will take months for the injury to heal, and that he could be sidelined for the rest of season.

Oswaldo Cabrera shared a note on Instagram following the successful surgery, “After such a sad night for me, having so many negative thoughts after twisting my ankle so brutally, in so much pain, I went to try to sleep so I wouldn’t give in to more bad thoughts. When I woke up, one of the first things I did was grab my phone. I didn’t have hundreds, I had THOUSANDS of messages from my family, friends, fans, agents, coaches, teammates…—I simply had messages from EVERYONE. I dropped the phone on the bed and with a big SMILE on my face, the first thing I could say was “God, how blessed I am.” Maybe it’s because it’s only after going through something like this that you realize the love that surrounds us. And TODAY, after a successful surgery with an excellent medical team and God, with my parents, my fiancée and my agent, my heart full of love, I want to THANK YOU ALL. Thank you for worrying about me, for every message, for keeping me in your prayers, for making me feel so supported. This is something that my family and I will never forget!"

He continued, "My return to the field begins today. Thanks to you, I feel more motivated than ever. So, with the strength I’ve always had and all this beautiful energy that you all give to me , I tell you that I will return, and I will return even stronger to continue giving my best every day. I LOVE U ALL” (Via @ocabrera13 on Instagram).  

Final Thoughts

On a more personal note, as a young Yankees fan (I was 12 in 2021), I was so excited to hear that the AA team for the Yankees would be moving closer to home. I grew up with the Somerset Patriots in the Atlantic League, going to friends' birthday parties, Little League events, and more at TD Bank Ballpark, but now that local team would be a real MiLB affiliate. My mom, Grandfather, and I eventually made our way to the ballpark in September, right before my first days of middle school, and although I had never watched a real minor league baseball game before, I fell in love. There is a different atmosphere in the minors, and Oswaldo Cabrera was a part of that first experience for me. I took my seat next to the Patriots’ dugout, and to my surprise, Oswaldo called me over and signed a ball for me, which came as a complete surprise. Yankee Stadium is famously hard to have player-fan interactions in, so when a kind-hearted player, who would later become a young star, took the time to talk to me, I was so excited.

Oswaldo has remained the same since that moment, as I have followed him throughout his path to the majors, and he has been the same generous and kind self when I have seen him, even in the Bronx. He helped grow my love of baseball to where it is today, and even in some ways has set me on the path to writing this article right now. Even in his message to the fans on-line, his true sincerity and love for the game and for the fans shine stronger than ever.

I hope he has a swift recovery and that all of us get to see him in New York again soon.