The Pittsburgh Pirates are keeping their options open this offseason. Unfortunately, Major League Baseball's calendar isn't offering them the same luxury.
Speaking at the GM Meetings in Las Vegas, general manager Ben Cherington emphasized that Pittsburgh isn't necessarily focused on addressing a predetermined list of positional needs. Instead, the organization intends to explore opportunities across the roster, whether through free agency or trades.
According to Colin Beazley of the Pittsburgh Post-Gazette, Cherington described the front office as open-minded about where improvements might come from, noting that Pittsburgh has a stronger foundation after its 82-win season.
In theory, that's a perfectly reasonable approach. The Pirates need more talent, and limiting themselves to specific positions could mean overlooking valuable opportunities elsewhere. But there's a significant difference between being flexible and being indecisive, especially when the clock is ticking toward a potential work stoppage.
Ben Cherington can't afford to let Pirates' offseason flexibility become an excuse for inaction
MLB's current collective bargaining agreement expires Dec. 1, and owners are widely expected to lock out the players. If that happens, major league transactions will effectively freeze until a new agreement is reached.
That gives Cherington roughly three weeks to turn his open-minded approach into actual roster improvements. He acknowledged that the trade and free-agent markets are developing more quickly than usual as teams prepare for the possibility of an extended shutdown but stopped short of suggesting that Pittsburgh would necessarily be among the clubs making moves before the deadline.
That's where things become concerning. The Pirates entered this offseason with legitimate momentum after finishing 82-80 in 2026, their first winning season since 2018. But that progress doesn't mean the roster is suddenly complete.
Brandon Lowe's uncertain future leaves Pittsburgh facing the possibility of losing its most productive power hitter. The bullpen needs reinforcement, the lineup remains vulnerable against left-handed pitching, and the organization could benefit from additional starting pitching depth.
While he has acknowledged that existing financial commitments and arbitration raises will affect the team's offseason approach, Cherington also insisted that the Pirates aren't financially constrained. That makes the stakes considerably higher.
There's nothing inherently wrong with refusing to overpay for a questionable fit or forcing a trade simply because a deadline is approaching. The Pirates shouldn't sacrifice valuable prospects just to create the appearance of urgency.
But waiting carries its own risks. Other organizations are operating under the same deadline, and some could move aggressively to secure their preferred targets before a lockout begins. Every meaningful signing or trade completed elsewhere potentially removes another option from Pittsburgh's board.
Ben Cherington at today's GM Meetings: "The only thing we're focused on is improvement... we'll pursue that through free agency and trade."
— SportsNet Pittsburgh (@SNPittsburgh) November 11, 2026
On the front office mindset when building the #Pirates roster: "Be urgent but not in a rush. Be ready." pic.twitter.com/cXV7bsgjOR
The Brandon Lowe situation illustrates the dilemma particularly well. Pittsburgh will receive some clarity when Lowe makes his qualifying offer decision by Nov. 17, but declining it wouldn't establish whether he'll ultimately return.
Cherington can't afford to let negotiations with one player dictate the pace of his entire offseason. Even if Lowe remains unsigned heading into December, the Pirates should have alternative plans ready to execute rather than allowing uncertainty to stall other opportunities.
Of course, a lockout wouldn't permanently eliminate Pittsburgh's ability to improve. Transactions would resume once a new labor agreement is reached, and some worthwhile players would presumably remain available.
But nobody knows when that might happen, what the market will look like afterward or how much time clubs will have to prepare for the 2027 season. That's an especially dangerous uncertainty for a franchise trying to build on its first winning season in eight years.
Cherington's willingness to consider improvements anywhere on the roster could ultimately prove advantageous. A team that isn't locked into one position can theoretically take advantage of opportunities that more narrowly focused competitors might overlook. But flexibility only matters if the Pirates are prepared to act on the opportunities they identify.
With a potential lockout looming, Pittsburgh cannot approach this offseason as though it has unlimited time to weigh its options.
The Pirates spent years waiting for their young core to develop into something worth building around. Now that they've finally taken a meaningful step forward, the last thing they can afford is another winter defined by patience rather than progress.
Cherington doesn't need to complete his entire offseason before Dec. 1. But he does need to make sure the Pirates have something to show for it before baseball's business potentially grinds to a halt.
