Is a flier on the struggling Luis Robert Jr. viable for the Padres?
Credit: AP Photo
With a major hole to fill in left field, Luis Robert Jr. has entered trade conversations once more.
It feels like a Luis Robert Jr. deadline blockbuster has been embedded into the MLB script for ages. In the case of the 2024 deadline, the notion intensified massively amidst the White Sox’s horrid 41-121 campaign. Fast forward to the upcoming 2025 deadline, and Robert Jr.’s name will likely find itself trending yet again.
While there have been better options in recent years, Robert Jr. stands out as one of the most attractive options. The bulk of the buzz around Robert Jr.’s profile comes from his 38-homer 2023 season. With that said, the bulk of the frequent lowball offers to acquire him come from his abysmal 2024 campaign. To add to the contrast, his 2025 has been even tougher, mustering just a .552 OPS through 55 games.
Luis Robert Jr. cranks his 4th home run in three games.
He ranks 2nd in the AL in HR. pic.twitter.com/KkVYc48lBk
— MLB (@MLB) June 27, 2023
However, the pool of left fielders that San Diego has utilized in 2025 have been no better. The difference is that none of them finished third in their league in SLG two years ago, or currently lead the league in stolen bases. Robert Jr. contains both of those potential upsides, along with his above-average defense.
In his first trade deadline report of the season, ESPN’s Jeff Passan highlighted Robert Jr. as the “Best fit” for the Padres. With safer and cheaper options on the table, it would seem farfetched, but with the Gavin Sheets coming out party in San Diego well underway, taking a flier on Robert Jr. could look more enticing to general manager A.J. Preller.
What does the ‘good version’ of a Luis Robert Jr. trade look like?
At the forefront of the answer has to be Robert Jr.’s production at the plate. Before examining the purchasing price, it all comes back to whether Robert Jr. hits well or not. That’s because he won’t just sell as the elite defender and baserunner that he is. Instead, the White Sox will likely leverage his 2023 season to a stubborn extent.
However, his miserable start to 2025 and inferable desire to be in a different uniform will weaken that leverage greatly. Additionally, the reasons for moving him would make plenty of sense. Robert Jr. will make $55M through 202, and is on the path that typically leads to a player being DFA’d. Dumping him while he’s still valued across the league could avoid paying some of his ugly contract.
In this case, the White Sox would likely ask for a pitcher to plug in immediately and solid prospect compensation, which would include one of the Padres’ two standout arms, such as Lake Elsinore’s Kash Mayfield or Boston Bateman. To fans’ relief, San Diego would be able to hold on to Ethan Salas and Leo De Vries for another deadline.
In turn, Robert Jr. would plug in to left field and buy into the team’s strong culture of togetherness. He would quickly drop any issues of attitude and provide RBI production out of the middle of the lineup. He would complete one of the best defensive outfields in the sport and cause havoc on the basepaths.
What does the ‘bad version’ of a Luis Robert Jr. trade look like?
Contrary to the club’s hopes, Robert Jr. wouldn’t be affected by the change of scenery or culture. The pitchers’ ballpark would just add to his frequent habit of flying out to the warning track. The swing and miss, the chase, wouldn’t improve past the slightest. The rolling snowball of missing production in left field would just enlarge.
Even worse would be if San Diego overpays to acquire a second player alongside Robert Jr. to go ‘all in’. This would likely mean the end of Salas’s tenure with San Diego, or more likely, a haul of pitching prospects. While it’s hard to see something like this playing out, Preller used this move to pull off the blockbuster for Juan Soto in 2022. While it would be scaled down, it would still evaporate too much of the farm system.
What would it take to pull it off?
Complexity. San Diego can’t afford to pay the full $55M of Robert’s dues, but could soften the burden in a few ways. Moving a reliever or two with heavier salaries would be the first option. Yuki Matsui is making $23M through 2028, and Wandy Peralta will make $12M through 2028. The other option would be to negotiate the salary with the White Sox and improve the package around it. While the White Sox wouldn’t be able to dump most of the contract, they’d avoid having to pay it in full and would get much cheaper prospects in return.
What are potential packages?
There are multiple ways San Diego could attack this, so we’ve outlined three packages that would make sense for both sides.
Package #1`
San Diego receives: OF Luis Robert Jr.
Chicago receives: LHP Yuki Matsui, LHP Kash Mayfield, OF Tirso Ornelas
This would essentially be the simplest outcome. The seasoned prospect Ornelas could find a home to adapt to MLB pitching, while Matsui would slot into the bullpen. The prized prospect would be Mayfield, and he would stack on to an impressive core of starting pitching prospects.
Package #2
San Diego receives: OF Luis Robert Jr.
Chicago receives: LHP Wandy Peralta, LHP Boston Bateman, OF Kavares Tears, 1B Romeo Sanabria
This deal would see a little more of the complexity promised beforehand. In this case, Chicago would take on the majority of the contract and receive larger prospect compensation as a result. Moreover, the veteran Peralta would be a more reasonable fit in the White Sox’s bullpen, and the Padres would rather part with him instead of Matsui. Lastly, Tears would pair up with Braden Montgomery around High Single-A, and Bateman would play Mayfield’s role from the previous package.
Package #3
San Diego receives: OF Luis Robert Jr.
Chicago receives: SS Cobb Hightower, RHP Braden Nett, OF Tirso Ornelas, RHP Tyson Neighbors, RHP Bradgley Rodriguez
This would be the big prospect dump that would see the White Sox buying into the luck of the haul strategy. Chicago would take on most of Robert Jr’s contract in exchange for a group of prospects that would likely give the White Sox a top-three farm system in all of baseball.
A 17-year-old San Diego native, Willy Warren is a baseball fan at heart who created High Leverage Baseball, a combination of around-the-league statistical analysis and breakdowns on X, and daily newsletters on the TikTok platform. Willy passionately studies Journalism at San Dieguito Academy, and is working to become billingual in Spanish to assist in communicating with Latin-born players and coaches.