Pirates Pursuing Cubs Free Agent Utility Man

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PITTSBURGH — The Pittsburgh Pirates have gone after many different free agents this season, but recently are targeting a player who can feature at a number of positions.
Jorge Castillo of ESPN reported that the Pirates have shown interest in free agent utility man Willi Castro. The Atlanta Braves and Colorado Rockies are two other teams that Castillo reported were also in on Castro.
The Pirates have mostly targeted big-time bats in free agency, but Castro represents a divergence from that.
What the Pirates Would Get in Castro
Castro is a seven-year MLB veteran and turns 29 years old next season, playing most of the past five seasons at the highest level of baseball. He can play most positions, including shortstop, second base and third base, as well as all three outfield spots.
Castro is a decent contact hitter, with a career slash line of .244/.313/.384 for an OPS of .697 and just 56 home runs over 705 games played.

He had his best season in 2024 with the Minnesota Twins, slashing .247/.331/.385 for an OPS of .716 in 158 games, with 138 hits, 31 doubles, five triples, 12 home runs and 60 RBI, earning him his first All-Star nod.
Castro spent his first four seasons with the Detroit Tigers, 2019-22, then signed with the Twins as a minor league free agent, having his best success from 2023-25, then spent the back end of last season with the Chicago Cubs, going there in a trade at the deadline.
Should the Pirates Go After Castro?
The Pirates generally like having a utiliy player like Castro on their roster, as they brought back Adam Frazier as a free agent last season and traded for Isiah Kiner-Falefa at the 2024 deadline. Castro would provide the Pirates a depth piece that could feature at any position that they need in 2026.
The Pirates have position needs at third base and left field, both positions where Castro has played. He started 125 of 164 games in left field and then started 64 of 105 games at third base.
While Castro can play all of these positions, he isn't the greatest defender, serving as an average outfielder and also having his struggles in the infield, with -2 defensive runs saved at third base and shortstop and -5 defensive runs saved at second base in 2025.
Castro also struggled with the Cubs during his time with them last season after the trade. He slashed .170/.245/.240 for an OPS of .485 in 34 games, with 17 hits in 100 at-bats.

Both MLB Trade Rumors and Kiley McDaniel of ESPN project him for a deal at two years, $14 million, while Spotrac has him at three years, $32,734,770, or $10.9 million AAV.
The $7 million a year salary is more manageable for a Pirates team that normally doesn't spend much in the free agency, but anything higher and it starts to become unreasonable for a player that hasn't shown great defense or a better bat to make up for it.
Who Else Are the Pirates Targeting in Free Agency?
Some of the names that the Pirates are looking at in free agency include NL MVP finalist Kyle Schwarber and catcher J.T. Realmuto of the Philadelphia Phillies, plus San Diego Padres designated hitter Ryan O'Hearn, Seattle Mariners second baseman Jorge Polanco and a pair of Japanese superstars in Kazuma Okamoto and Munetaka Murakami.
The Pirates reportedly offered Schwarber a four-year deal north of $100 million, which would obliterate the franchise record signing for a free agent.
All of these players, aside from Realmuto, have shown power and great bats over the years, at varying rates, but the consistent theme is the Pirates searching for that in free agency.
The Pirates haven't signed a free agent of real note yet, but with the Winter Meetings going on in Orlando, Fla., there could be some moves coming soon.

Dominic writes for Pittsburgh Pirates On SI, Pittsburgh Panthers Pn SI and also, Pittsburgh Steelers On SI. A Pittsburgh native, Dominic grew up watching Pittsburgh Sports and wrote for The Pitt News as an undergraduate at the University of Pittsburgh, covering Pitt Athletics. He would write for Pittsburgh Sports Now after college and has years of experience covering sports across Pittsburgh.