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More than a decade ago, the Yankees signed a 16-year-old Venezuelan shortstop as part of their international free agent class. He was by no means the biggest name in it, nor did he receive the most money from the Yanks in that class.
Half a decade later, he debuted with the Yankees and had an abbreviated, yet electric rookie season. Unfortunately, a sophomore slump hit hard. Since then, he’s never recovered at the plate — worse, a brutal injury cost him most of the 2025 season. Despite all that, Oswaldo Cabrera’s versatility, baseball IQ, and outstanding attitude have made him a surprisingly important player for the Yankees, and I think we’re all looking forward to seeing him back in pinstripes in 2026.
Oswaldo Alberto Cabrera
Born: March 1, 1999 (Guarenas, Venezuela)
Yankees Tenure: 2022-present
In July 2015, the Yankees signed a then-16-year-old Oswaldo Cabrera for $100,000 as part of that year’s international free agent class. The Yanks had spent a boatload of money the year before (to a horrifically scant return, as it turns out), so they were capped at $300,000 per signing. For fans who’ve followed the Yankees minor-league system, names including Luis Medina, Deivi Garcia, and Andres Chaparro were part of the 2015 IFA class as well.
Young Waldo began the 2016 season at Rookie Ball, and from there embarked on the same journey thousands of prospects before him took: the long, slow climb up the MiLB ladder. By the time the 2018 season approached, Ozzie found himself on the prospect radar, albeit at the back end of the Yankees’ system. FanGraphs ranked him 26th on their list, remarking:
“Cabrera has advanced feel to hit, not much power, and the ability to play both positions up the middle… It’s a utility profile but with good odds given the advanced bat and feel for the game.”
Cabrera continued to toil in the minors, losing valuable development opportunities (as all prospects did) when COVID-19 brought the world to a screeching halt in 2020. Then 2021 happened. Defying the “not much power” assessment, Oswaldo clubbed 29 home runs across Double- and Triple-A and put together a 31-game on-base streak that summer.
His performance did not go unnoticed. Minor League Baseball named him the Double-A Northeast Most Valuable Player and he shot up various pre-season prospect rankings for 2022, with MLB placing him 14th on their rankings and FanGraphs slotting him in at No. 13. Unfortunately for Cabrera, on the cusp of the major leagues, the injury bug reared its head. A shoulder injury cost him approximately two months in early 2022. Upon his return, however, Waldo was unstoppable, putting together a .330 batting average with a 1.040 OPS in 25 games.
With the Yankees scuffling, Cabrera’s time had come. Losers of 11 of their last 13 games during the dog days of August, New York called him up to the Bronx. It took no time for him to make an impact. Two days after his call-up, he was in right field on a Friday night at Yankee Stadium. On the first pitch of the game, he flashed some leather. And some hops. Instant home run robbery.
Cabrera saw most of his playing time in right field. But he was nonetheless almost everywhere, seeing time at first, second, and third base, shortstop, and left field. All the while, he kept showing off defensively and delivering at the plate. By the time the playoffs rolled around, he was firmly ensconced in the Yankee lineup.
In his first taste of playoff baseball, Cabrera struggled, though he did come through for the Yanks in a huge spot. Facing Triston McKenzie in the top of the fifth inning in Game 3 of the ALDS in Cleveland, Cabrera came to the plate in a tied game in a tied series. With Harrison Bader on first base, Waldo launched a two-run home run to right field, looking into the Yankee dugout for good measure before rounding the bases. His knock gave the Yankees the lead, until a brutal bullpen meltdown in the ninth inning cost them the game, though they went on to win the series.
As magical as his debut seemed, Ozzie’s sophomore season was abysmal. He was almost an automatic out when he stepped into the batter’s box, “boasting” a 59 wRC+. I guess if there was one good thing, he checked another position off his to-do list on August 31st, when he saw time in center field for the first time.
Two years later, with the Yanks on the wrong end of a blowout against the Dodgers, he stepped onto a big-league mound for the first time and even recorded an out. All that remains is for him to don the tools of ignorance at some point and get behind the plate.
Cabrera has never rediscovered the form at the plate he showed in ‘22. He’s been particularly hapless against southpaws, with a career .576 OPS when facing portside slingers. Despite his struggles at the dish, his ability to capably defend at multiple positions has made him a valuable player for Aaron Boone and the Yankees.
To the distress of everyone, Waldo suffered a gruesome injury on May 12th that ended his season. He and the Yankees recently received good news, however. Earlier this week, Boone announced Cabrera could see game action as soon as the end of the first week of March. That would be one heck of a late birthday gift for a young man who seems to be genuinely liked by the entire organization. Happy birthday Waldo, and with any luck, we’ll see you back on the field and at the plate in a few days.
References
Badler, Ben. “International Reviews: New York Yankees.” Baseball America. March 28, 2016.
“INF Oswaldo Cabrera Named Double-A Northeast MVP.” MiLB. October 6, 2021.
Joyce, Greg. “Red-hot Oswaldo Cabrera joining Estevan Florial as call-up to reeling Yankees.” New York Post. August 17, 2022.
McDaniel, Kiley. “Top 27 Prospects: New York Yankees.” FanGraphs. March 26, 2018.
Miller, Randy. “Yankees injuries: Latest on Cam Schlittler, Anthony Volpe, Oswaldo Cabrera.” NJ.com. February 25, 2026.
Oswaldo Cabrera. Baseball-Reference.
Oswaldo Cabrera. FanGraphs.