Unless something desperately needed to happen occurs between today and Sunday, Ben Cherington will be in charge of selecting the Pirates organization’s picks in the 2025 MLB amateur draft, which will take place in Atlanta starting at 6 p.m. on both MLB network and ESPN. Sunday will include the first 105 picks in draft’s first three rounds and will continue at 11:30 a.m. Monday on MLB.com with rounds four through 20.

Cherington in charge of player draft in 2025 scares me. And it’s not just the first pick he will make when the Pirates’ sixth place in the draft order comes up; it’s the total of close to two dozen players who will be called upon to lead the club in a few years.

It’s not just the drafting, but the development and guidance to get them from the 2025 chart of draftees to their names on the back of the major-league uniform.

This will be Cherington’s sixth draft, and while he has had some success in drafting pitchers, some of whom are even healthy as you read this, he has drafted in those six chances nary an offensive player for a Pirates team that has desperately needed someone who can hit—not even one on the major-league roster.

Nick Gonzales comes the closest, and he was never in the top 10 voting in 2025. In fact no Pirates made the list of top 10 among the 15 National League teams.

Cherington had the good fortune of being the GM whose team won the 2023 draft lottery and allowed Paul Skenes to drop onto their pitching mound.

And while there have been some among Cherington’s six Pirates draft classes who have been labeled with the “can’t miss” curse, we have not seen anyone besides Skenes, a sure-fire pick to pitch in next week’s All-Star game, even sniff at success in Pittsburgh.

“We want to deliver more to our fans as fast as we possibly can,” Cherington said recently. “These next [few] weeks will bring opportunities that we can use to our advantage, and we have to be ready for that. I think what that means more than anything, is to go into this open-minded. We’re not delivering enough; we need to deliver more.”

And that brings up the second July event that terrifies me even more: the 6 p.m. July 31 trade deadline for the rest of the 2025 season.

As weak as the Cherington draft and development has been, his trade record has been even worse. In his first off-season before the 2020 60-game season, he traded Starling Marte for Brennan Malone and Liover Peguero; pre-2021 he swapped and Josh Bell for Wil Crowe and Eddie Yean; he sent Jamison Taillon and Joe Musgrove packing for David Bednar, Hudson Head, Drake Fellows, Omar Cruz, Endy Rodriguez, Roansy Contreras, Miguel Yajure, Canaan Smith-Njigba, and Maikol Escotto. Mid-season send-offs included Adam Frazier, Clay Holms, Tyler Anderson, and Rich Rodriguez for Jack Suwinski, Tucupita Marcano, Mitchell Miliano, Hoy Park, Diego Castillo, Carter Bins, Joaquin Tejada, Bryse Wilson, and Ricky DeVito.

He sent Jacob Stallings to Miami for Zach Thompson, Conner Scott, and Kyle Nicolas before the 2022 season. At mid-season he sent Daniel Vogelbach aud Jose Quintana for Colin Holderman, Chris Stratton, Johan Oviedo, and Malcolm Nunez.

Before 2023, he sent Kevin Newman for Dauri Moreta, and Nick Garcia for Connor Joe, and DeVito for Mark Mathias. Mid-season, he shipped out Robert Stephenson for Alika Williams, Carlos Santana for Jhonny Severino, Rodolpho Castro for Bailey Falter, and Rich Hill and Ji Man Choi for Jackson Wolf, Alfonso Rivas, and Estaur Suero.

Before the 2024 season, Pittsburgh traded Deivus Nadal for Edward Olivares, bought Marco Gonzales, and sold Roddery Munoz.

During the trade deadline they shipped out Martín Pérez, Quinn Priester, Charles McAdoo, Luis Peralta, Garret Forrester, and Patrick Reilly for Ronaldys Jimenez, Nick Yorke, Isiah Kiner-Falefa, Jalen Beeks, Billy Cook, Josh Walker, and Bryan De La Cruz.

Of that group, only Bednar has provided any level of importance.

In addition, During Cherington’s tenure, the Pirates have never kept a signed free agent for the entire season, except for McCutchen.

I can’t for the life of me think why owner Bob Nutting would allow Cherington to make any moves during this weekend’s draft or the trade deadline.

Can you?