Pirates Could Make One Deadline Move Fans Never Saw Coming

As the Pittsburgh Pirates eye a postseason breakthrough, strategic roster enhancements could be the key to turning their playoff ambitions into reality.

The Pirates reached the All-Star break in a spot they haven’t occupied in years: above .500, in the race, and still with room to get better.

At 50-47, Pittsburgh is over the break-even mark at this point for the first time since 2016. The club sits two games behind the final NL Wild Card position, which puts the front office in a position it has rarely had lately - deciding how hard to push as a buyer.

General manager Ben Cherington made clear the Pirates are open to that possibility.

“I’ve said we believe in this team and we want to find ways to improve it,” Cherington said. “We know some of that has to happen internally.

We’ve wanted to keep our eyes out externally for opportunities to improve, strengthen and deepen our roster. That can happen anytime, that can happen any day.”

Cherington’s comments came Wednesday, a day after shortstop Konnor Griffin landed on the injured list. Even with Griffin and Jared Triolo in the picture, Cherington said shortstop was not initially a major focus.

Still, he added that the club would be more open-minded about upgrading there. Then on Friday, Pittsburgh sent the No. 34 pick in the MLB Draft to the White Sox in a deal for shortstop option Jacob Gonzalez.

The Pirates also appear willing to look at the outfield. Cherington pointed to that area as another possible upgrade, especially after the team traded offense for defense in the offseason and wound up with a minus-12 fielding run value so far. Oneil Cruz will come back from a fractured left hand after the All-Star break, but he has a minus-2 fielding run value in center field.

Pittsburgh’s recent history at the Deadline suggests caution. When the club has been out of contention before August, it has usually sold.

That included the deal that sent closer David Bednar to the Yankees hours before the 2025 Deadline in exchange for three prospects. The Pirates also picked up Evan Sisk and Callan Moss from the Royals for Bailey Falter, and sent Ke’Bryan Hayes to Cincinnati for prospect Sammy Stafura.

What happens over the 16 games between Tuesday’s All-Star Game and the Aug. 3 Trade Deadline will go a long way toward shaping the Pirates’ approach.

If they keep hanging around, they could act like buyers. If not, the old pattern may take over.

There is also some help coming from inside the building. Spencer Horwitz, Cruz and Endy Rodríguez are expected back soon after the break, giving Pittsburgh a boost to an offense that has already been one of the league’s best.

The rotation has generally held its own, aside from Mitch Keller’s 5.14 ERA in 19 starts. The bullpen is where the need is loudest. Wilber Dotel is set to return from the injured list shortly after the break, and Sisk is expected back at some point as well.

Even so, the relief corps has struggled to find dependable arms. Pittsburgh’s bullpen ERA sits at 4.48, fourth worst in the NL.

That’s why right-handed help, or any arm capable of handling high-leverage spots, would matter so much. It would allow Gregory Soto to shift around and give manager Don Kelly more options late in games.

Brandon Eisert’s addition gives the Pirates four reliable left-handers once Sisk returns, but the need for steady righties remains. Dennis Santana has not found consistency all season.

One possible trade chip could come from the major league roster itself. Horwitz is under club control through 2028, and with Esmerlyn Valdez emerging in right field, Ryan O’Hearn may fit better at first base. That makes Horwitz an intriguing piece if Pittsburgh decides to deal from the big league level in order to add pitching.

Cruz may be the most important player on the second-half board. Before his left hand fractures sidelined him for more than a month, he was tracking toward a historic 40-home run, 60-stolen base season.

Only Ronald Acuña Jr. has ever finished that kind of year. With the Pirates already running a top offense, Cruz’s return could make it even more dangerous.

The bigger question is whether Pittsburgh can keep its place in the Wild Card mix while waiting on all those bats. Five NL teams are within five games of the final playoff spot entering the break, so the margin is tight. The Pirates will also have to navigate series against current postseason teams like the Guardians, Yankees and Cubs, likely without Cruz, Horwitz and Rodríguez.

If the weekend against the Brewers is any clue, though, Pittsburgh may be ready for the fight.

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