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The Chicago White Sox set a record last season. Unfortunately for them, it is not a record they want to hold. Chicago lost 121 games in 2024, more than any other team in Major League Baseball history. After that, every bit of success the White Sox have had in 2025 is a good sign. The team is young and energetic, even if it is inexperienced as a whole.
As the team makes moves, it is important to understand what their overall goal is. Chicago is not trying to make the playoffs or win a championship this season. Instead, they want to put themselves in a position to be in the playoff conversation for years to come in the future. That means picking their targets well and balancing their lineup with young stars and veteran leadership.
Luis Robert Jr. has been in trade rumors for years now, but Chicago is unlikely to move him. He is a part of the last White Sox team that was a contender in the American League. Now, he is a mentor to the team's younger players as they find their way at the professional level. Because of that, his value to the team goes beyond what he gives them on the field.
Here are three players that Chicago could target at this year's trade deadline. They could either fit into the team's long term plan or bring their experience to their clubhouse.
Tampa Bay Rays Right Fielder Jose Caballero
Jose Caballero has played at a variety of positions for the Rays so far this season. The 28-year-old is in his third season as a pro and his second with Tampa Bay. He is a much better fielder than he is a batter, but given more opportunity, he could grow into more than what he is now. If nothing else, he is a player who can handle a heavy workload, playing over 100 games in the past two seasons.
Caballero is batting .250 on the season(as of May 16) with just one home run. His usage all over 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 move their expendable pieces, including Caballero.
The White Sox are an underwhelming team at every position with the exception of second and third base. Caballero would walk through the door as a player that Will Venable can put at the position of most need. His consistent contributions could help steady the ship and help make the Chicago offense at least a bit respectful to offer some help to their young starting rotation.
Los Angels Angels Shortstop Tim Anderson
Tim Anderson and Robert Jr. were the leaders on the 2021 White Sox. That team won more than 90 games, winning the American League Central and making the playoffs. While Robert Jr. is still with the team, Anderson still has fond memories of his time in Chicago. What better a move at the trade deadline than one that reunites the former All-Star with the team that gave him his first shot in the major leagues?
Anderson offers more as a veteran presence than he does on the field. That is part of the reason why the Angels have him backing up Zachary Neto. He has not been the same since 2022, but a homecoming could be just what the 31-year-old needs to reinvigorate his career. Chase Meidroth has shown promise at shortstop, but the 23-year-old is in need of a mentor.
Los Angels likely considers Anderson an expendable asset and would be willing to listen if the White Sox called about his availability. Stars that moved on from the team they broke out with often return later in their career. Anderson returning to Chicago would be a great full-circle moment for him.
Pittsburgh Pirates Relief Pitcher David Bednar
In a shift of strategy, David Bednar is a player who can help the White Sox now and in the future. The 30-year-old is a two-time All-Star capable of baffling the best of hitters at the end of tight games. The Pirates demoted and promoted Bednar this season, but he has been with the team since April 19.
Bednar was a victim of the Pirates' slow start to the season, but has yet to overcome his struggles since returning He's been unseated by Dennis Santana as the team's closer and is trying to adjust to his new role as a set up man. However, there are a few teams in need of bullpen help that could offer him a chance at their closer role if he can return to his All-Star self.
Over the last two seasons, Bednar was impressive, notching over 20 saves in 2023 and 2024, including a career-high 39 in 2023. On the White Sox, he would be the de-facto closer thanks to his experience. Whether they are relievers or starters, MLB pitchers have shown a habit of maintaining their effectiveness as they get older. At 30 years old, Bednar isn't old yet, making him a great option for Chicago to pursue.
The trade deadline is an opportunity for all teams to take one step closer to their goals. That looks different for each team, but the White Sox stand to gain a lot if they make the right moves this summer. If they pull off effective trades, their rebuild could end sooner than anticipated.
