Pirates’ most impactful pre-lockout offseason roadmap starts with a decision Ben Cherington can’t delay

With Major League Baseball's collective bargaining agreement set to expire December 1 and a lockout widely expected to follow, the Pittsburgh Pirates face an unusually compressed offseason calendar. They could have fewer than three weeks remaining to complete trades and free-agent signings before transactions are potentially frozen indefinitely.

At the GM Meetings in Las Vegas, Ben Cherington insisted that the Pirates aren't financially constrained, despite increased arbitration costs and existing contractual commitments. He also emphasized that the organization isn't necessarily targeting specific positions, preferring to remain open to improvements throughout the roster.

That approach has merit under normal circumstances. But with a potential work stoppage approaching, flexibility without urgency could become a serious liability.

The Pirates need a plan that prioritizes immediate improvements without allowing their biggest offseason question — Brandon Lowe's future — to dictate every other decision.

Pirates' four-step pre-lockout plan could make or break their 2027 season

November 9-12: Turn GM Meetings conversations into legitimate trade opportunities

The GM Meetings typically provide an opportunity for front offices to establish relationships, evaluate the market and lay the groundwork for moves that materialize later in the winter. This year, Pittsburgh can't afford to treat them as merely an information-gathering exercise.

Cherington should leave Las Vegas with concrete trade frameworks in place, particularly for a right-handed hitter capable of addressing the Pirates' longstanding struggles against left-handed pitching. That weakness isn't dependent on Lowe's future. Even if Pittsburgh manages to retain its star second baseman, the lineup still desperately needs better balance.

Third base should also be a priority. Nick Gonzales' offensive emergence was encouraging, but his defensive struggles at the position complicate his long-term fit. Jared Triolo offers substantially better defense, though his offensive ceiling remains limited.

The Pirates don't necessarily have to complete a trade during the meetings. But they should identify realistic targets, establish acquisition costs and prepare to act quickly if negotiations advance.

By November 17: Get clarity on Lowe without letting his decision control everything

November 17 is arguably the most consequential date on Pittsburgh's immediate offseason calendar. That's when Lowe must decide whether to accept or reject the Pirates' one-year, $23.15 million qualifying offer.

Coming off a 35-home-run, 96-RBI season, Lowe is widely expected to decline the offer and pursue a multiyear contract. Cherington has confirmed that conversations with Lowe and his representatives remain ongoing, but no agreement appears imminent.

Lowe declining the qualifying offer doesn't mean he's leaving Pittsburgh. It simply means he remains available in free agency. That's precisely why Cherington cannot afford to wait for Lowe to make his ultimate decision before pursuing other improvements.

The Pirates need two parallel plans: one that accounts for Lowe returning and another that addresses his potential departure. Both should already be underway.

November 17 also marks the deadline to protect eligible prospects from the Rule 5 Draft by adding them to the 40-man roster. Catcher/first baseman Axiel Plaz is among the organization's most intriguing protection candidates after hitting .305 with 18 home runs at High-A Greensboro. Pittsburgh must also evaluate several other eligible prospects while weighing the implications of a possible lockout for players added to the 40-man roster.

Those decisions matter beyond prospect preservation. They directly affect how much roster flexibility Cherington has to complete major league acquisitions.

By November 20: Make arbitration decisions with the bigger picture in mind

Pittsburgh has 10 arbitration-eligible players, including Paul Skenes, Oneil Cruz, Nick Gonzales, Jared Triolo and Henry Davis. The November 20 non-tender deadline will force the front office to determine which players remain part of its plans for 2027.

For several players, those decisions should be straightforward. Others require more consideration. Triolo, for example, presents an interesting dilemma. His defensive versatility has obvious value, particularly given Pittsburgh's uncertainty on the infield. But the Pirates must decide whether that value justifies his projected salary and roster spot.

The larger objective should be establishing a realistic payroll framework before entering the final stretch of November. Cherington has already acknowledged that arbitration raises will influence Pittsburgh's approach. If the front office genuinely believes it has enough flexibility to improve, it needs to demonstrate how those financial commitments fit into a plan that includes outside additions.

Simply tendering contracts to everyone and postponing difficult roster decisions until after the lockout would accomplish very little.

November 21-30: Stop evaluating every possibility and start completing deals

The final stretch before the anticipated transaction freeze should be Pittsburgh's most aggressive period. By this point, the Pirates should understand their projected arbitration commitments, know Lowe's qualifying-offer decision and have a clearer picture of their available 40-man roster spots. That should allow Cherington to pursue free agents and finalize trade discussions without the same degree of uncertainty.

The Pirates have needs beyond second base, including another right-handed offensive contributor, dependable bullpen depth and potentially additional infield help. Those opportunities won't necessarily remain available once baseball resumes normal business.

There's also no guarantee that the market will look remotely similar after a lockout. Teams could face an entirely different competitive landscape depending on the outcome of labor negotiations.

The current CBA expires at 11:59 p.m. ET on December 1, meaning a lockout could begin December 2. If that happens, major league trades and free-agent transactions would be suspended. For Pittsburgh, the objective should be entering that uncertainty with at least one meaningful roster upgrade already completed — preferably more.

The Pirates can't control whether MLB owners impose a lockout, how long a potential stoppage lasts or what the next collective bargaining agreement looks like. They can, however, control whether they enter that stoppage having done everything possible to strengthen their roster.

The clock is ticking. Cherington's biggest mistake would be acting as though he still has all winter.

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