By the 2021 trade deadline, general manager Ben Cherington appeared to have his Pittsburgh Pirates well-stocked with middle infield prospects. He had just obtained Diego Castillo, Tucupita Marcano, and Hoy Park in trades. In January 2020, he picked up prized prospect Liover Peguero from the Arizona Diamondbacks. Ji Hwan Bae and Rodolfo Castro were already in the system. What could go wrong?
Plenty, as it turns out. With Bae and Peguero having recently been placed on waivers, none of the “big six” are presently in the Pirates organization. The failures of these players prompted Cherington to go out and get Nick Yorke at the 2024 trade deadline. It shows that prospects are far from a sure thing. Let’s look at where they failed and where they are now.
Pirates System No Longer Deep in the Middle Infield
The Enigma
Castro was just 16 years old when the Pirates signed him as an amateur free agent in 2015. After hitting .248/308/.436, 54 HR, and 239 RBI in 413 games across all levels in the Pirates system, he looked like he was in the majors to stay when he came up in July 2021. His first five major league hits were home runs. But there were also signs of immaturity. There were emotional displays that looked silly from a player struggling to hit his weight on a bottom-feeding team. Finally, after a hitless August 21, the Pirates returned Castro and his .198 average to the minors.
Castro returned to the big club in May 2022, vowing to play so well that the Pirates would never think of sending him back to the minors again. However, an incident of non-hustle on June 4 against Arizona drew a rare public rebuke from then-manager Derek Shelton. Back went Castro to the minors. He returned to Pittsburgh in August, only to be part of an embarrassing incident when his cell phone popped out of his pocket as he slid into third base.
Finally, Cherington traded Castro to the Philadelphia Phillies for Bailey Falter at the 2023 trade deadline. When Castro played against his former team that September, he could be seen trotting to first base each time he grounded out. It was odd behavior from a player who was 3-for-24 for his new team entering the Pirates series. After 14 games with the Phillies, he spent the next two seasons in the minors. As of last week, he became the Toronto Blue Jays’ problem. He’s on a minor league deal with the Jays, with an invitation to spring training.
The Speedster
Bae’s failures have been well documented on these pages and needn’t be detailed again. The South Korean was a free agent signee by the Bucs in 2018. Bae plays in the middle infield and the outfield, but it was his speed and on-base skills that had the Pirates salivating. Alas, his .385 minor league on-base percentage never translated to the majors, where he showed a frustrating tendency to chase pitches. During the 2025 season, the Pirates gave up on him as an infielder and used him exclusively in the outfield at Triple-A Indianapolis and at Pittsburgh. Then last month, they gave up on him completely.
The New York Mets claimed Bae off waivers on November 6 and currently list him on the active roster. The word is that he’ll get a fair shot at playing some center field for them. They’ll need to work hard with him on plate discipline.
The Former Shortstop of the Future
Similarly, Peguero’s failures have been covered exhaustively on this site. Thought to be the shortstop of the future when he was acquired in 2020, it never panned out for him. Some might argue that he never got a fair chance with Pittsburgh, playing in just 96 games from 2022-2025. While there might be more than a grain of truth to that, it gets to the point where the team needs the player to get ready on their timetable, not his. Peguero’s minor league batting average has declined each year since 2023 as well. He hit just .247 at Indy in 2025. As of this writing, he’s 5-for-28 in the Dominican Winter League.
The Phillies, who apparently haven’t had their fill of Pirates middle infield rejects, signed Peguero to a minor league deal on November 19. There’s been no word on whether he’ll receive a spring training invitation. If so, he’ll have the proverbial uphill climb to go north with a deep Phillies squad.
The Roving Gambler
Marcano came to the Pirates from the San Diego Padres in a 2021 deadline deal that sent Adam Frazier the other way. Marcano never got on track with the Pirates. In 124 games with Pittsburgh from 2022-2023, he hit .221/.267/.334. The Pirates placed him on waivers after the 2023 season, and the Padres reclaimed their former prospect. In June 2024, Major League Baseball banned him for life for gambling on baseball. (Another former Pirate, pitcher Luis Ortiz, was recently indicted on gambling charges by Department of Justice prosecutors in Brooklyn. MLB is expected to render discipline by spring training. Where the hell are the Pirates finding players? At the craps table?)
An Ill-Fated Trade
Pirates fans would love to undo, or at least forget, the trade of pitcher Clay Holmes to the New York Yankees for middle infield prospects Castillo and Park. In 96 games with Pittsburgh in 2022, Castillo hit .206/.251/.382, 11 HR, and 29 RBI. One would think the Pirates would have at least been intrigued by his power, but they moved on from Castillo quickly, trading him to Arizona after that season. The guy who came up with the “join the Navy, see the world” slogan might be interested in Castillo’s travels. Castllo’s career has taken him to 17 cities for eight organizations. He became a free agent last November. Organization No. 9 hasn’t come calling yet.
Park is the answer to two baseball trivia questions. The first is: Who was the Pirates’ Opening Day second baseman in 2022? The second is: Who on Earth is Hoy Park? The left-handed hitter holds his bat high like Carl Yastrzemski, but comparisons with the Boston Red Sox legend end there. Like Bae, Park is a South Korean who’s flashed good on-base skills in the minors in the form of a .366 OBP. Like Bae, Park couldn’t replicate this skill in the majors. After Park posted a .202/.293/.348 slash line in 2021-2022 with the Bucs, he was traded to Boston.
Subsequently, he landed with the Atlanta and Oakland organizations. He wasn’t terrible with their Triple-A clubs, hitting .262 with Gwinnett in 2023 and .254 with Las Vegas in 2024. Even so, he hasn’t played in the majors since his time with Pittsburgh. He elected free agency on November 6, 2024, but didn’t find a suitor. Park didn’t play professionally in 2025. He’ll be just 30 years old in April. Presumably, he’ll answer the phone if it rings.
Main Photo Credits: Charles LeClaire-Imagn Images
The post The Pirates Were Once Stocked with Middle Infield Prospects. appeared first on Last Word On Baseball.