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Pirates Ready to Strike at Trade Deadline

The Pittsburgh Pirates will look to make some big moves to bolster their roster.
Jun 5, 2024; Pittsburgh, Pennsylvania, USA;  Pittsburgh Pirates general manager Ben Cherington speaks on the phone in the dugout before the Pirates host the Los Angeles Dodgers at PNC Park. Mandatory Credit: Charles LeClaire-USA TODAY Sports
Jun 5, 2024; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates general manager Ben Cherington speaks on the phone in the dugout before the Pirates host the Los Angeles Dodgers at PNC Park. Mandatory Credit: Charles LeClaire-USA TODAY Sports | USA TODAY Sports via Reuters Connect

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PITTSBURGH — The Pittsburgh Pirates are five days away from the Aug. 3 trade deadline and look primed to make some important moves.

The Pirates are fighting in a tense National League Wild Card race, sitting one game back of the final playoff spot, and have a team that could seriously make their first postseason since 2015.

Buster Olney of ESPN noted the Pirates as one of 12 teams desperate to add at the trade deadline, particularly when it comes to finding bullpen help.

He spoke with a rival staffer, who said the Pirates are "going to be aggressive," and thtey have the starting pitchers and hitters to make a real run at it.

"That rotation is [explicit] real," the rival staffer said to Olney, "and they can score."

Pirates GM Ben Cherington Ready to Pounce at Trade Deadline

If there's one person that will need to have a great trade deadline for the Pirates, it's none other than general manager Ben Cherington.

Cherington is in his seventh season and the Pirates haven't had the success that is needed for him to stay in the job for the foreseeable future, if they fail this year.

Pittsburgh Pirates general manager Ben Cherington
May 12, 2026; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates general manager Ben Cherington looks on during batting practice before the game against the Colorado Rockies at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | IMAGN IMAGES via Reuters Connect

He made some important additions this offseason, like signing slugger Ryan O'Hearn to a two-year, $29 million deal, plus trading for second baseman Brandon Lowe, outfielder Jake Mangum and left-handed relief pitcher Mason Montgomery from the Tampa Bay Rays in a three-team deal that sent Mike Burrows to the Houston Astros.

Cherington will have to improve the roster at the trade deadline, with the bullpen a focus point, as the Pirates have struggled closing out games and holding onto leads.

The Pirates general manager told local media that they have the "flexibility" to go and make the moves they need and that they are working constantly to achieve the goal of bettering the roster when the deadline comes.

"We feel urgency every day," Cherington said. "Everybody has a job to do to get better. That starts with me. That urgency is felt. I think we just have to stay at it. We’ve already done some things that we felt made sense at the time and felt were improvements to the roster. We should be using every minute we have to our disposal. We still have a lot of minutes left in the next few days to use. Keep working it.

"Believe there are parts of the team that are working well and we believe are gonna be strengths as we get deeper into the season. There are things we want to improve still also..."

Why the Pirates Will Add at the Trade Deadline

The Pirates have a real chance to make the postseason for the first time in more than a decade, and it's a combination of internal development and great external additions.

Pittsburgh has a strong starting rotation, with the likes of Cy Young winner Paul Skenes, All-Star Braxton Ashcraft, veteran Mitch Keller, emerging rookie Bubba Chandler and Jared Jones, who has been brilliant in July after his return from internal brace surgery in late May.

Pittsburgh Pirates starting pitcher Paul Skenes
Jul 25, 2026; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates starting pitcher Paul Skenes (30) delivers a pitch against the Chicago Cubs during the first inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | IMAGN IMAGES via Reuters Connect

The Pirates' offense has been one of the best in baseball, making a full turnaround from 2025, either leading or being closer to the top in numerous statistical categories.

External additions in O'Hearn, Lowe and Mangum have all played important roles in the Pirates' offense excelling, but internal improvements from the likes of Nick Gonzales, Spencer Horwitz, Oneil Cruz, Bryan Reynolds and Endy Rodríguez have also been crucial this season.

The Pirates have the rotation and offense, but will need some bullpen additions, which generally can come as "overpays", but ones the team must be willing to make, especially with how important a great bullpen is to making the playoffs and winning once a team is there.

Make sure to visit Pirates OnSI for the latest news, updates, interviews and insight on the Pittsburgh Pirates!

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Dominic Campbell
DOMINIC CAMPBELL

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.