The Chicago White Sox set a record last season. Unfortunately for them, this is not a record they wish to keep. Chicago lost 121 games in 2024, more than any other team in MLB history. After that, any success the White Sox have had in 2025 is a positive sign. The team is young and energetic, despite its overall lack of experience.
As the team makes decisions, it is critical to understand what their overall goal is. This season, Chicago’s goal is not to make the playoffs or win the championship.
Instead, they want to position themselves to be in the playoff conversation for many years to come. That entails carefully selecting their targets and balancing their roster with young stars and veteran leadership.
Luis Robert Jr. has been the subject of trade rumors for several years, but Chicago is unlikely to move him. He was a member of the last White Sox team that competed in the American League.
Now, he serves as a mentor to the team’s younger players as they navigate the professional level. As a result, his value to the team extends beyond his contributions on the field.
Here are three players who Chicago could pursue at this year’s trade deadline. They could either contribute to the team’s long-term strategy or bring their experience to the clubhouse.
Tampa Bay Rays Right Fielder Jose Caballero
Jose Caballero has played a variety of positions for the Rays this season. The 28-year-old is in his third season as a professional, the second with Tampa Bay.
He is a much better fielder than a batter, but with more opportunities, he could develop into something more than he is now. If nothing else, he is a player who can handle a heavy workload, having played more than 100 games in the previous two seasons.
Caballero is batting.250 this season (as of May 16), with only one home run. His versatility on the field is a good thing, but Kevin Cash has yet to pencil him in as an everyday starter for his team. The Rays are under.500 more than a month into the season, putting them in a position to trade their expendable players, including Caballero.
The White Sox are mediocre at every position except second and third base. Caballero would walk through the door as a player that Will Venable could place in the position of greatest need. His consistent contributions could help to steady the ship and make the Chicago offense more willing to help their young starting rotation.
Los Angels Angels Shortstop Tim Anderson
Tim Anderson and Robert Jr. led the 2021 White Sox. That team won more than 90 games, won the American League Central, and advanced to the playoffs. While Robert Jr. is still on the team, Anderson has fond memories of his time in Chicago. What better trade deadline move than one that reunites the former All-Star with the team that gave him his first opportunity in the majors?
Anderson brings more of a veteran presence than he does on the field. That is one of the reasons the Angels have him backing up Zachary Neto. He hasn’t been the same since 2022, but a homecoming could be exactly what the 31-year-old needs to rekindle his career. Chase Meidroth, 23, has shown promise as a shortstop, but he needs a mentor.
Anderson is likely an expendable asset for the Los Angeles Angels, and they would be willing to listen if the White Sox inquired about his availability. Stars who leave the team with which they rose to prominence frequently return later in their careers. Anderson’s return to Chicago would be a great full circle moment for him.
Pittsburgh Pirates Relief Pitcher David Bednar
In a shift in strategy, David Bednar is a player who can benefit the White Sox both now and in the future. The 30-year-old is a two-time All-Star capable of perplexing the best hitters at the end of close games. This season, the Pirates demoted and promoted Bednar, but he has been with the team since April 19.
Bednar was a victim of the Pirates’ slow start this season, but has yet to overcome his struggles since returning. Dennis Santana has replaced him as the team’s closer, and he is adjusting to his new role as a setup man. However, if he can regain his All-Star form, a few teams in need of bullpen help may consider giving him a shot at the closer position.
Bednar was impressive over the last two seasons, recording more than 20 saves in 2023 and 2024, including a career-high 39 in 2023. With his experience, he would be the White Sox’s de facto closer.
MLB pitchers, whether relievers or starters, have a history of remaining effective as they age. Bednar is only 30 years old, making him an excellent option for Chicago to pursue.
The trade deadline provides an opportunity for all teams to move one step closer to their goals. That looks different for each team, but the White Sox stand to benefit significantly if they make the right decisions this summer. If they make effective trades, their rebuilding efforts may be completed sooner than expected.
