When the MLB trade deadline rolls around, Chicago White Sox outfielder Luis Robert Jr might be the most coveted player available. The White Sox will then have a major decision on their hands.
Robert is only 27-years-old and is under team control through the 2027 season. With the White Sox so far out of contention, it seems advantageous for Chicago to swing a trade. But they’ve yet to pull the trigger, perhaps in hopes that he lead the team’s lineup of the future.
Still, if Robert is truly made available, numerous teams around the league will be putting in offers. Former general manager and current analyst for The Athletic Jim Bowden thinks the San Diego Padres should get involved. He proposed a trade in which the White Sox would land prospects Kash Mayfield, Kavares Tears and Cobb Hightower for Robert.
“The White Sox have been dangling Robert in talks with teams for a while, but after he got off to an awful start this season, interest quickly diminished,” Bowden said. “That doesn’t mean contending teams don’t understand Robert’s value, when he’s right, as he’s proven he can be a 30-home run, 20-stolen base, Gold Glove-winning player.”
“Several teams would like to trade for him, but I like the fit with the Padres, where he could play left field alongside Jackson Merrill in center and Fernando Tatis Jr. in right,” he continued. “I think Robert would flourish with a change of scenery and could thrive if he joined a clubhouse with players like Manny Machado, Tatis and Jake Cronenworth. There’s certainly nowhere to go but up: Robert is batting a paltry .194/.279/.311, though he does have 21 steals.”
Luis Robert Jr joins San Diego Padres

While it’s still too early to start watching the standings, the Padres currently hold the third National League Wild Card spot with their 39-33 record. As they battle to remain in the playoffs, it wouldn’t be shocking to see San Diego buy at the deadline. Especially with general manager AJ Preller at the helm.
As it stands, the Padres rank 19th in runs scored with 304. They’ve been impressive at limiting the strikeouts – third-fewest at 512 – but it’s clear they need a bit more thump in the lineup. Adding Robert to a core that already features Jackson Merrill, Fernando Tatis Jr and Manny Machado should bring some extra fireworks.
That is of course if Robert finds his footing with a change of scenery. He is hitting a weak .190 this season with six home runs and 28 RBI. Robert’s 21 stolen bases are tied for fourth-most in the league. But the Padres or any team acquiring the outfielder would be expecting him to return to his 20/20 caliber of play.
It’s going on two seasons now since Robert was voted to his first All-Star Game. But in 2023, Robert opened everyone’s eyes by hitting .264 with 38 home runs, 80 RBI and 20 stolen bases. The outfielder has proven to be a menace on the basepaths, he just needs to find his consistency at the plate.
The Padres are in need of an offensive boost and are trying to vie for the playoffs. The White Sox are simply focused on improving for the future. Overall, both sides at least match up as trade partners.
Chicago White Sox continue to build for future

If the White Sox finally decide it’s time to trade Robert, they will further look at each interested team’s best prospects. Bowden’s projected trade would give Chicago three of San Diego’s best.
Mayfield, a left-hander pitcher, ranks as the No. 3 prospect in the Padres organization, via MLB Pipeline. The No. 25 overall pick in the 2024 MLB Draft, Mayfield has put up a 3.91 ERA and a 37/9 K/BB ratio over his first eight starts in Single-A. While he has a long way to the majors, he would make for another star pitcher for the White Sox to build around.
Hightower was another 2024 draft pick, landing with the Padres in round three. The shortstop now ranks as the sixth-best prospect in the organization. Over his first 14 games at Single-A, Hightower has hit .235 with four RBI. Like Mayfield, Hightower would be a long-term project for the White Sox. But one that comes with tantalizing potential.
Tears is the No. 7 overall prospect in San Diego’s farm system. He was a fourth-round compensatory pick in 2024, meaning the White Sox would be acquiring some of the best talent from the Padres’ most recent draft class. In his first 48 games of Single-A ball, Tears has hit .258 with seven home runs, 38 RBI and two stolen bases.
Despite Robert’s struggles, Chicago will ask for a haul based on the outfielder’s years of control remaining. If they got this deal from the Padres, their farm system would be infused with eye-catching prospects and the future would only look brighter on the South Side.
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