Trading outfielder Andrew Benintendi will be no easy task for the Chicago White Sox. However, it’s clear he no longer fits their rebuilding vision. If teams are going to call about Benintendi, the White Sox are surely listening with open ears and wide eyes.
The biggest roadblock is Benintendi’s contract. He is making over $15 million a season through 2027. While Chicago is reportedly willing to include cash in any Benintendi trade, that’s still a hefty hit an acquiring team would need to take on. The outfielder hitting .233 isn’t helping matters either.
But left handed bats are always needed at the trade deadline. Benintendi is up to 10 home runs and 32 RBI after hitting 20 bombs and driving in 64 RBI in 2024, so perhaps a change of scenery is all he needs.
The San Diego Padres have been connected to fellow White Sox outfielder Luis Robert in numerous trade rumors. However, Kerry Miller of Bleacher Report argues the Padres should target Benintendi, offering prospect Clark Candiotti in return.
“Plain and simple, it’s a salary dump,” Miller wrote.
“The White Sox are almost certainly going to either trade away Luis Robert Jr. or decline his $20M club option for next season. It’s also a near certainty their $10M mutual option with Martín Pérez won’t be exercised, leaving Benintendi ($17.1M in 2026, $15.1M in 2027) as the only already known salary heading into next season.”
“Trading him away would allow them to fully, symbolically turn the page to whatever this franchise’s next chapter may be. Getting a lottery-ticket prospect in the deal just makes it a little sweeter,” he concluded.
Andrew Benintendi joins Padres
With a core featuring Fernando Tatis Jr, Jackson Merrill and Manny Machado, the Padres will be battling for a playoff in the second half of the season. However, to do so, San Diego needs to find an answer in left field.
“To put it lightly, left field has been an adventure for the Padres, with nine players combining for a sub-.600 OPS. They released Jason Heyward on Wednesday, and he had been the team leader in plate appearances in left,” Miller wrote. “Gavin Sheets has been fine as the primary offering there in recent weeks. However, when he’s in left, DH becomes the adventure for San Diego.”
There will likely be stronger options available on the trade market. But in terms of pure prospect capital, all of them will cost more than Benintendi. The Padres would be taking a gamble, but Benintendi would at least solidify their left field situation.
For the White Sox, Candiotti ranks as the No. 26 overall prospect in the Padres’ organization, via MLB Pipeline. He was a fourth-round pick in 2024, making 10 appearances at the High-A level thus far. The right-hander holds a 5.40 ERA and a 43/22 K/BB ratio, making him a true dart throw for Chicago.
Still, if it helps get Benintendi’s contract off the books, the White Sox should be open to a deal.
Chicago White Sox turn to Philadelphia Phillies
The Padres aren’t the only team in need of a left-handed bat. The Philadelphia Phillies are trying to hold off the New York Mets in the NL East and need a bit extra juice. While it would also cost relief pitcher Steven Wilson, Joel Reuter of Bleacher Report argues he and Benintendi should be traded to the Phillies for prospect Michael Mercado.
“Paying his 2026 and 2027 salaries down to something in the $5-7 million range might help get a deal done, as would packaging him with a useful bullpen arm like Steven Wilson, who has a 1.73 ERA, 1.19 WHIP and 8.7 K/9 in 27 appearances and comes with club control through 2027,” Reuter wrote.
“The motivation here for the White Sox is to shed salary, so the return would be minimal. Michael Mercado is a former top prospect who signed an above-slot $2.1 million deal as a second-round pick in 2017,” he concluded. “Trading him would open up a 40-man roster spot for the Phillies and provide a change of scenery.
Wilson should be a hot commodity on his own based on his 2025 numbers. Furthermore, he is under team control through 2027 at an affordable rate. He arguably could be the White Sox’s best trade piece at the deadline. Packaging him alongside Benintendi may be the best way to shed the outfielder’s contract. With the Phillies always seemingly in need of bullpen help, they’d certainly be intrigued by the inclusion of Wilson.
Mercado ranks as the No. 23 overall prospect in Philadelphia’s organization, via MLB Pipeline. Like Candiotti, he would be a lottery ticket more than anything else. The righty has made it into eight major league games. But those outings have resulted in a 11.81 ERA and a 14/13 K/BB ratio.
Everyone will be focused on Robert leading up to the deadline. But the White Sox will be looking for ways to trade Benintendi as well.
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