Pirates Should Trade for Yankees All-Star

The Pirates have already targeted left-handed hitting second basemen as trade targets in Brandon Lowe of the Tampa Bay Rays, Jeff McNeil of the New York Mets, plus St. Louis Cardinals infielders like Brendan Donovan and Nolan Gorman.

PNC Park is beneficial for left-handed hitters, with the right field wall much closer than the left field wall, particularly in deep center field.

The Pirates also have gone after left-handed hitting bats in free agency like Kyle Schwarber and Jorge Polanco and still have some targets available like Munetaka Murakami and Ryan O'Hearn.

Chisholm also has a year of arbitration remaining and the Pirates could try and not just trade for him, but sign him to an extension, making him a key part of the future of the franchise.

He has hit 108 home runs over his six MLB seasons, but 55 of them have come in the past two seasons.

The Pirates finished last season with the least home runs in baseball at just 117, 31 less than the second-least team in the Cardinals at 148 home runs. They also posted the worst slugging percentage (.350) and OPS (.655) of any MLB team.

Chisholm's 31 home runs, .481 slugging percentage and .813 OPS would easily serve as the best on the Pirates in 2025, with Oneil Cruz leading the team with just 20 home runs.

Whether or not those other trade targets or left-handed batters in free agency don't pan out, the Pirates must at least show interest in Chisholm this offseason.

Pirates Miss Out on Chisholm in 2024

The Pirates were interested in trading for Chisholm at the 2024 deadline, with the Miami Marlins looking to offload their star player.

Chisholm would've given the Pirates what they wanted this offseason the rest of 2024 and also in 2025.

The Pirates instead traded for Marlins outfielder Bryan De La Cruz, who had an awful tenure at the end of 2024, with a -1.2 WAR and slashing .200/.220/.294 for an OPS of .514 in 44 games, earning him a non-tender at the end of the season.

Chisholm, instead, ended up with the Yankees and excelled in his time in the Bronx in 2024, slashing .273/.325/.500 for an OPS of .825 in 46 games with 11 home runs and 23 RBI.

He then had an incredible 2025 season with the Yankees, earning his second All-Star nod, winning his first Sliver Slugger Award and becoming just the third player in franchise history to record at least 30 home runs and 30 stolen bases, joining the 30-30 club.

The Pirates front office can only look back on regret that they missed out on a top talent like Chisholm, but they can still rectify things this offseason.