Pirates may need to abandon their most obvious trade strategy as MLB lockout looms

The Pittsburgh Pirates entered the offseason knowing they needed to acquire proven major league talent. But with a potential MLB lockout looming on Dec. 1, general manager Ben Cherington may have to reconsider one of the most straightforward ways to accomplish that goal: trading prospects for established players who can help immediately.

According to MLB Network's Jon Morosi, trade discussions across the league are progressing faster than usual ahead of this week's GM Meetings in Las Vegas. However, Morosi also reported Sunday that teams may be reluctant to exchange prospects for players entering their final season of club control because of uncertainty surrounding the 2027 schedule.

That creates an interesting dilemma for the Pirates, who need to improve their major league roster without compromising the young talent that could sustain its recent progress.

The Pirates have spent years assembling a promising collection of prospects, and their first winning season since 2018 demonstrated that their competitive window might finally be opening. Trading some of that organizational depth for immediate help makes sense, but trading it for a player who might only be available for a shortened season is a much harder sell.

Pirates' trade priorities could change dramatically because of looming labor stoppage

Morosi specifically identified Steven Kwan, Joe Ryan, Logan Gilbert and Sandy Alcantara as potential trade candidates whose remaining contract control could complicate negotiations. All four are scheduled to become free agents after the 2027 season.

Under ordinary circumstances, acquiring an established player with one year remaining on his contract might be an attractive option for a team looking to accelerate its competitive timeline. But these are hardly ordinary circumstances.

With the current collective bargaining agreement set to expire Dec. 1, there is no guarantee that the 2027 season will begin on schedule. A lockout wouldn't automatically mean canceled games, but the possibility of an extended labor dispute introduces considerable uncertainty into every potential transaction.

For the Pirates, that uncertainty should change the calculation. Kwan, for example, would offer the kind of reliable offensive approach and defensive consistency Pittsburgh could use. Ryan or Gilbert would provide another established arm to complement Paul Skenes and the organization's emerging young rotation.

However, none would come cheaply under normal market conditions. And the prospect cost becomes increasingly difficult to justify if Pittsburgh cannot count on receiving a full season of production before those players reach free agency.

There's also an uncomfortable parallel to the Pirates' most successful trade from last offseason. Cherington acquired Brandon Lowe from Tampa Bay, and the veteran second baseman responded with 35 home runs and 96 RBI in 2026. It was an outstanding short-term addition, but Lowe is now testing free agency, leaving Pittsburgh facing the possibility of losing one of its most productive hitters after just one season.

The Pirates got tremendous value out of that acquisition. That doesn't necessarily mean they should repeat the strategy under significantly less predictable circumstances.

Ben Cherington may need to prioritize long-term control over immediate impact

Morosi also suggested that teams could consider exchanging players entering their final years of control for one another, effectively spreading the risk rather than surrendering prospects.

That might work for organizations with comparable expiring assets to exchange, but Pittsburgh's situation is different. The Pirates' most valuable trade currency comes from their prospect pipeline and young major league talent. They can't afford to spend those assets carelessly, particularly when their competitive window should extend beyond 2027.

Instead, Cherington would be better served targeting players with multiple seasons of control remaining, even if acquiring them requires a different approach or a more complicated negotiation.

Of course, that strategy comes with challenges of its own. Players with additional years of control generally command larger trade returns, and Pittsburgh can't assume that teams will suddenly become willing to part with affordable, controllable talent. Still, the Pirates would at least have a better chance of receiving meaningful long-term value for whatever prospects they surrender.

And none of this means Pittsburgh should abandon its win-now ambitions. After finishing 82-80 in 2026, the Pirates have every reason to pursue improvements aggressively rather than wait for their prospects to develop. But being aggressive doesn't have to mean being reckless.

Cherington has already demonstrated that acquiring an established player approaching free agency can produce immediate results. Now, with the threat of a labor stoppage hanging over the offseason, he needs to recognize when that same approach might carry more risk than reward.

The Pirates can't afford another offseason of standing still, nor can they afford to sacrifice valuable pieces of their future for a 2027 season whose length remains uncertain. If that means passing on some of the most recognizable names on the trade market in favor of players who can contribute well beyond next season, so be it.

Pittsburgh's competitive window shouldn't depend on how quickly MLB and its players can negotiate a new labor agreement.

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