Predicting White Sox's next big trade before deadline

As the 2025 MLB trade deadline approaches, the Chicago White Sox find themselves in a familiar position, firmly entrenched as sellers. With a record that has left them buried at the bottom of the American League standings, the White Sox have little hope of salvaging their season. Instead, the focus has shifted to the future, and the front office is preparing to leverage its few remaining assets to accelerate a long-overdue rebuild.

Who’s on the Block?

Predicting White Sox's next big trade before deadline — Matt Marton-Imagn Images

Chicago’s roster features a mix of expiring contracts, veterans, and a handful of players with significant trade value. Among the most discussed are outfielders Luis Robert Jr. and Andrew Benintendi, starting pitchers Adrian Houser and Aaron Civale, and several relievers, including Cam Booser and Tyler Alexander.

Luis Robert Jr., despite a down year at the plate, remains the club’s most intriguing trade chip. His Gold Glove-caliber defense and elite speed have kept his value afloat, even as his offensive numbers have dipped. With team-friendly club options for 2026 and 2027, Robert is under control for the foreseeable future, making him an attractive target for contenders willing to bet on a rebound.

Adrian Houser, meanwhile, has emerged as a surprise asset. Signed to a one-year deal, Houser has delivered strong performances in the rotation, and his affordable contract makes him a logical candidate for a deadline move. The White Sox also have other veterans, such as Aaron Civale and Michael A. Taylor, who could appeal to teams seeking depth for the stretch run.

The Predicted Blockbuster Trade

While several deals are likely in the works, the most significant trade expected before the deadline involves Luis Robert Jr. The buzz around the league is that the San Francisco Giants, desperate to inject athleticism and defense into their outfield, are the frontrunners to land Robert. The Giants have the prospect capital and the financial flexibility to absorb his contract, especially if the White Sox are willing to include cash to improve their return.

The Giants’ outfield has struggled with injuries and inconsistency, and Robert’s defensive prowess and base-stealing ability could be the spark their lineup needs. Even with his offensive struggles, Robert’s upside is tantalizing for a team looking to make a deep playoff run. For the White Sox, moving Robert represents an opportunity to restock the farm system with high-ceiling talent.

Projected Trade Proposal

White Sox receive:

Grant McCray
Hayden Birdsong
Marco Luciano
cash considerations

Giants receive:

Luis Robert Jr.
cash considerations

This package gives the White Sox three top-15 prospects from the Giants’ system. Grant McCray is an athletic outfielder with plus speed and defensive skills, Hayden Birdsong is a high-upside right-hander with strikeout stuff, and Marco Luciano is a power-hitting infielder with All-Star potential. The inclusion of cash from Chicago helps offset Robert’s salary and maximizes the return.

For the White Sox, trading Robert is both a painful and necessary step. His value, while diminished from its peak, is still significant due to his defensive reputation, base-running, and contract structure. The return of three high-upside prospects aligns perfectly with Chicago’s stated goal of adding young, controllable talent—not long-term projects, but players who can contribute soon.

For the Giants, acquiring Robert is a bold move that addresses multiple needs. His glove and speed immediately upgrade their outfield defense, and his offensive upside offers hope for a second-half surge. With the NL West race wide open, this is the type of swing that could push San Francisco into serious contention.

The White Sox’s willingness to move a player of Robert’s caliber signals a true commitment to rebuilding. Fans may lament the loss of a Gold Glove center fielder, but the reality is that the team’s competitive window is years away, and maximizing the return for their best asset is the prudent move. The infusion of talent from a deal of this magnitude could reshape the organization’s trajectory for years to come

As the deadline nears, expect the White Sox to be among the most active sellers, with Robert’s name dominating the rumor mill. This predicted deal with the Giants stands out as the next big trade to get done, a move that will define Chicago’s 2025 deadline and set the course for a new era on the South Side.

The aftermath of this trade will be closely watched not just in Chicago and San Francisco, but across the league, as it could set the tone for other rebuilding clubs considering similar moves. For White Sox fans, patience will be required, but the hope is that this bold strategy finally brings sustained success to the South Side. The next few weeks will reveal if the front office can execute this vision and lay the groundwork for a competitive future.