The Pirates went into the offseason with a clear mission: add proven major league help. But the path that usually makes the most sense - flipping prospects for an established player - may not be nearly as clean this year with a potential MLB lockout looming on Dec. 1.
That uncertainty has already started to reshape the trade market. According to MLB Network’s Jon Morosi, clubs are moving faster than usual ahead of this week’s GM Meetings in Las Vegas. Even so, Morosi reported Sunday that teams may be hesitant to deal prospects for players with only one year of club control left because nobody knows what the 2027 schedule will look like.
For Pittsburgh, that creates a real problem. The Pirates need to improve the big-league roster, but they also have to protect the young talent that has helped push the organization forward.
Morosi named Steven Kwan, Joe Ryan, Logan Gilbert and Sandy Alcantara as possible trade candidates whose control situation could make deals tricky. All four are set to reach free agency after the 2027 season.
In a normal market, that kind of player would be exactly the sort of target a team like Pittsburgh might chase. Kwan would bring steady offense and dependable defense. Ryan or Gilbert would give the Pirates another established starter to pair with Paul Skenes and the rest of the young rotation.
But this isn’t a normal market. With the current collective bargaining agreement set to expire Dec. 1, there’s no guarantee the 2027 season will start on time. A lockout wouldn’t automatically wipe out games, but it does inject a lot of uncertainty into any deal involving a player nearing free agency.
That matters because the price won’t be small. Under standard conditions, those players would cost real prospect capital. If Pittsburgh can’t be sure it will get a full season of production before free agency hits, that cost becomes much harder to swallow.
There’s also a cautionary example sitting right there from last offseason. Ben Cherington traded for Brandon Lowe, and the veteran second baseman delivered 35 home runs and 96 RBI in 2026. It was a huge short-term win for the Pirates, but Lowe is now testing free agency, which leaves Pittsburgh staring at the possibility of losing one of its most productive bats after just one year.
That doesn’t mean the move was a mistake. It does mean repeating that formula now comes with more risk than usual.
Morosi also noted that teams could look to swap players who are themselves entering their final years of control, spreading out the risk instead of paying in prospects. That kind of deal can work when both sides have matching pieces to move, but Pittsburgh’s strongest trade currency is its prospect pool and young major league talent. The Pirates can’t afford to spend that lightly, especially with a competitive window that should stretch beyond 2027.
That points Cherington toward a different kind of target: players with multiple seasons of control left. Those players are harder to get and usually cost more, but at least the return would come with longer-term value.
None of this means the Pirates should slow down. After finishing 82-80 in 2026, they have every reason to keep pushing for upgrades. But being aggressive and being reckless are two different things.
Cherington has already seen how an established player close to free agency can pay off right away. Now he has to decide whether that same play is worth the danger when the labor picture is cloudy and the 2027 season itself is uncertain.
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