Pirates GM Cherington Discussed Hitting, Free Agents with MLBTR

Pirates GM Cherington Gives Wide-Ranging Interview

Too often, Cherington is his own worst enemy from a public relations standpoint. He whiffs on softball questions designed to appease an angry fan base. He doesn’t let his hair down and let fans see a side of him that might allow them to set aside their anger over how the team is run and find him at least somewhat likable. Before McDonald got to the tough questions, Cherington showed that he indeed has a sense of humor and a human side. It turns out Cherington reads MLB Trade Rumors and has even gotten ideas for transactions from the site. When McDonald jokingly suggested a finder’s fee, Cherington quipped, “We’re a small market team. Keep that in mind.” For those fans interested in his dietary habits, he hasn’t caught on to Pittsburgh’s tradition of french fries in sandwiches or salads.

Of course, Pirates fans want his head on a platter, and the Pirates can even hold the fries. Despite being buried in last place in Year 6 of a five-year rebuilding plan, Cherington continues to speak as though he expects to be Pirates GM for a long time yet. The jury is still out on that notion. More on that in a bit.

On Development of Hitters

Cherington agreed that it was “fair” to say that the Pirates have developed pitchers better than they’ve developed hitters under his watch. Pirates fans might be surprised to know that it was never his intent to “be heavy on the pitching side.” He said they put just as much effort into hitting as they do into pitching. After making some valid points about why hitting isn’t as easy to develop as pitching, he said, “I’m actually really encouraged by the processes that we’re putting in place” in the past 18 months or so.

As Pirates GM, Cherington has been a steadfast believer in his “processes.” The collective groan coming from the direction of western Pennsylvania is the Pirates fan base lamenting, “Here we go again.”

The Pirates’ hitting has been better lately. Entering Thursday’s game at St. Louis, they’ve won seven of their last nine games. They’ve scored 44 runs in those games. Even so, throughout the course of the season, one watches Pirates batters take hittable pitches and wonders whether their minds are too cluttered with information. New hitting coach Matt Hague promised a more individualized approach to coaching in a spring training interview. Yet, nothing seemed to change. As a team, the Pirates’ slash line is .234/.305/.352. They’re dead last in the majors in slugging, and the other two figures are near the bottom as well.

“Stop Doing That”

Not that it’s turned Davis into the next Cal Raleigh, however. Since that talk with Lamont, he’s gone 8-for-36, albeit with two home runs. But the incident demonstrates that there’s an old-school approach that’s been missing from the Pirates’ “processes.” It’s fair to ask why Davis apparently never heard anybody say to look for a pitch down the middle until his fifth year in the organization.

On Multi-Year Deals with Free Agents

Cherington said he’s made multi-year offers to free agents on behalf of the Pirates and has been turned down. That’s not new information. What’s new is that these offers were made to position players, not pitchers, and he hasn’t “made a lot of them.” He mentioned there’s “some portion of the free agent pool” that he’s “not going to spend as much time on,” presumably the Juan Sotos of the world.

Cherington continued, “Aside from dollars and term, winning is going to be the first thing you hear up on the list of priorities” of free agents. This contradicts my long-held belief that this breed of mercenary ballplayers would play on Jupiter if the dollars were there. I’m not privy to these negotiations and am unlikely to ever be invited to sit in on one. After all, Cherington didn’t say whether he read Last Word On Sports as much as he reads MLB Trade Rumors. Thus, I’ll take his word for it that winning is No. 1 with free agents.

The Conundrum, and Other Multi-Syllabic Words

This puts Cherington and the Pirates in quite a conundrum. They can’t sign a premier hitter to a multi-year deal unless they win, but they can’t win without better hitters. It makes development, which they haven’t been good at, all the more important.

One 2025 free agent who I thought should have been a slam dunk for the Pirates was outfielder Max Kepler. Kepler didn’t have a great 2024 season. However, the 11-year veteran has hit at least 19 home runs in a season five times. He had his best season in 2019, when he hit 36 homers and drove in 90 runs for the Minnesota Twins. Minnesota’s bench coach that season was Derek Shelton, who began this season as the Pirates manager. I thought Cherington could have sold Kepler, a left-handed batter, on PNC Park’s short right field and a reunion with Shelton.

Alas, Kepler signed a one-year deal with the Philadelphia Phillies, where he’s reportedly unhappy about his platoon status. Of course, a .216/.299/.375 slash line will relegate a guy to a lesser role. I don’t know whether the Pirates pursued Kepler, and in hindsight, it probably wouldn’t have worked out anyway. But he wasn’t expensive, and it’s an example of low-hanging fruit that never got picked, for one reason or another.

The Last Word

Whether Pirates owner Bob Nutting brings Cherington back for 2026 will be interesting to see. Nutting may be impatient with the lack of results and more attuned to fan disenchantment than he’s been in the past. On the other hand, Cherington speaks confidently and persuasively of his plans for the organization, as indicated in the interview, and this is what Nutting hears every day. We await Nutting’s next move – or lack thereof.