Ben Cherington has spent years asking Pirates fans to stay patient. This winter, though, his own timeline may leave Pittsburgh with a much shorter leash.
With Major League Baseball facing the possibility of a lockout when the current collective bargaining agreement expires Dec. 1, the Pirates’ general manager has already said the club needs to be ready to move fast. Cherington told reporters after the season that Pittsburgh wants its offseason priorities identified early enough to take advantage of any opening before a transaction freeze.
“We have to be ready for it,” Cherington said. “By November, we’ll have a clear idea of what we want to accomplish in the offseason. And then, we at least have November to see what we can do.”
Now it’s November, and that quote lands differently. It sounds like preparation. It also sounds like a promise - one the Pirates can’t really afford to miss.
Under ordinary circumstances, there’s nothing reckless about waiting for the market to settle. For a team working with Pittsburgh’s financial limits, patience can sometimes create value.
Free-agent prices shift. Trade talks evolve.
A slow burn can work.
This winter is not ordinary. If owners lock things down when the current agreement runs out, trades and free-agent signings would stop until a new deal is reached. That could wipe out weeks, maybe months, of time for teams trying to patch holes and build a better roster.
For the Pirates, that should mean urgency, not hesitation.
Pittsburgh finished 2026 at 82-80, good for its first winning season since 2018. That’s real progress, but it still wasn’t enough to get the club back to the postseason. Seven seasons into the rebuild, the improvement matters - but it doesn’t finish the job.
And the roster still has clear issues. The Pirates need help against left-handed pitching.
They need steadier production at third base. They need more pitching depth.
They also have to deal with the possibility of losing Brandon Lowe, whose 35 home runs and 96 RBI made him one of their most important bats.
The lockout threat makes all of that messier, but it doesn’t remove the responsibility to address it.
Pittsburgh can’t make free agents sign early, and it can’t force other teams to strike a deal before December. Some of the answers may not be available until after a new labor agreement is in place. But there’s a big difference between being unable to finish a move and not pushing hard enough to make one happen.
The Pirates have enough established talent now to justify a more aggressive winter. They’ve reached the point where waiting for perfect conditions is no longer a luxury they can afford.
Cherington has already said the club needs to be prepared for a compressed offseason. That puts November squarely in the spotlight, and it turns his front office’s next few weeks into a real test of whether it can turn progress into action.
If the Pirates come out of a long lockout next spring with the same holes still staring them in the face, fans will have every right to wonder whether the work stoppage was just bad luck - or just another excuse.
Cherington has preached patience for years. This offseason, his words make it clear: the time for action is here.
In Other News...
Pirates Face A Costly Lefty Decision With Real Rotation Risk
As the Pirates look for help on the left side of their rotation, Jim Bowden has put two very different names in the conversation: Robbie Ray and Foster Griffin. Both would represent a meaningful financial commitment, and both would come with their own questions, which is exactly why the decision feels so delicate for a club trying to add pitching without boxing itself into a bad deal.
Ray brings the appeal of a former Cy Young winner, but the injury history and uneven recent performance make him a difficult bet. Griffin is the younger option and comes off a strong season after returning from Japan, which gives Pittsburgh a more sensible long-term path even if there are still concerns about consistency. For a Pirates rotation that needs stability, the choice is less about star power than about how much risk the front office is willing to absorb. [Read more 🡒]
Pirates Face A Costly Rotation Question They Cant Ignore
The Pirates long-range rotation picture has a glaring shape to it, and it is one the front office can already see coming. As things stand, Pittsburgh projects toward a 2027 starting staff made up entirely of right-handers, which is why the club may need to add left-handed depth before that becomes a more obvious problem. It is the kind of roster imbalance that does not always show up in the short term, but can matter a great deal once the calendar turns and the matchups get tighter.
One name that fits the need is Trevor Rogers, a left-handed free agent with a track record that makes him appealing even with some injury questions attached. The fit is easy to understand from Pittsburghs side, but the harder part is the price and the risk, especially with payroll always part of the conversation for this team. Whether the Pirates actually make that kind of commitment remains uncertain, but the need for another lefty is not going away anytime soon. [Read more 🡒]
Pirates Shortstop Prospect Is Forcing A Bigger Future Debate
Wyatt Sanfords rise this fall has added another layer to the Pirates long-term infield picture. The shortstop prospect earned a spot as a Fall Star in the Arizona Fall League after a strong run with the Glendale Desert Dogs, putting himself among nine National League infielders chosen for the Fall Stars Game. For a player who has been trending upward all season, it was another sign that his bat is starting to match the defensive reputation that made him worth watching in the first place.
Sanfords 2026 season already showed real progress in his overall hitting, and the next checkpoint should come at Double-A Altoona next year. That level will matter a lot for the Pirates, because it is where his development starts to feel less theoretical and more tied to the major league timeline. If he keeps pushing forward there, the organization may have a tougher decision ahead about just how quickly his future can be accelerated. [Read more 🡒]