If Pittsburgh is serious about contending during Paul Skenes’ prime, a cash-assisted trade for Luis Robert Jr. could make sense for both sides.
A new team has emerged as a potential trade partner for Chicago White Sox center fielder Luis Robert Jr.—that is, if the price is right and an offer compelling enough materializes to change Chicago’s stance about keeping him for 2026.
That team could be the Pittsburgh Pirates.
There has been plenty of hype this offseason surrounding the Pirates being uncharacteristically aggressive in free agency, attempting to add proven bats and make a legitimate push toward the postseason. With a generational talent like reigning Cy Young Award winner Paul Skenes anchoring the rotation, Pittsburgh would be foolish not to capitalize on his prime years—especially while he’s still pitching on a rookie contract.
That urgency explains why now is the time for the Pirates to act. Improving the offense is a must. But Pittsburgh has already missed on several key free-agent targets, most notably Kyle Schwarber, who returned to the Philadelphia Phillies on a five-year, $150 million deal.
It’s going to take more than one or two free-agent signings to get the Pirates where they need to be. And if they’re going to invest significant money into the roster, it makes sense to explore other avenues of improvement that could help control costs—namely, the trade market.
Now, before going any further, it’s worth noting that the White Sox exercised Luis Robert Jr.’s $20 million club option for the 2026 season. Any deal sending him to Pittsburgh would almost certainly require Chicago to eat a sizable portion of that contract.
Naturally, that raises questions about owner Jerry Reinsdorf’s willingness to do so.
That concern would feel more pressing if the money were headed to Steve Cohen and the New York Mets—something John Heyman recently reported Reinsdorf is not particularly inclined to do.
That’s on brand for the White Sox chairman.
But Pittsburgh might be a different story.
According to Ken Rosenthal of The Athletic, “While Robert has drawn interest from the Mets and Philadelphia Phillies, he might be more likely to end up with a low-payroll team that ends up striking out on free agents—the Pittsburgh Pirates, for example. To make such a deal happen, the White Sox almost certainly would need to include cash to make Robert more affordable. They are open to doing that as a way of enhancing the return, according to a club official.”
So let’s assume the White Sox are willing to do exactly that—eat salary to maximize the return—and send Robert Jr. to Pittsburgh. What might a deal look like?
Two names to watch: Edward Florentino (Pirates No. 5 prospect, MLB No. 81) and Esmerlyn Valdez (Pirates No. 16).
It may be wishful thinking to believe the White Sox could land a player of Florentino’s caliber in a one-for-one deal centered around Robert Jr. It’s also possible that additional pieces would need to be involved. But Florentino fits exactly what Chicago has been trying to add to its rebuild.
The 19-year-old left-handed hitter plays first base and the outfield and posted a .948 OPS with 16 home runs last season, reaching A-ball for the first time. He’s long and lanky at 6-foot-4, with natural power, athleticism, and strong reviews for his work ethic and character—rare traits to already have attached to a teenager.
Whether Florentino ultimately settles into a corner outfield spot or first base, his left-handed offensive upside is the type organizations dream on. More importantly, it would address a clear void in the White Sox farm system.
Valdez, meanwhile, is closer to the big leagues and could factor into Chicago’s plans as soon as 2026.
Between High-A and Double-A in 2025, he slugged 26 home runs, drove in 86 runs, and posted an .896 OPS. He truly put himself on the map in the Arizona Fall League, where he crushed eight home runs in just 19 games and finished with a staggering 1.355 OPS.
The White Sox need power, and Valdez has it in abundance. His long-term defensive home remains uncertain, but Chicago is in a position to continue developing him in the outfield and see whether he can stick in a corner. If not, first base remains an option.
It may be an unconventional path, but the Pirates have the prospect depth to make a deal work—especially if the White Sox are willing to eat a portion of Luis Robert Jr.’s salary to maximize the return.