What began as a total rebuild last July will culminate in a final push to completely demolish Chicago’s payroll and hopes of winning 50 games.

After dealing several veterans at the 2024 trade deadline, Chicago’s trade ambitions are much higher this year. This go-around, the Sox aim to trade Luis Robert Jr. and Andrew Benintendi, and they’re kicking in some cash to sweeten the pot, according to The Athletic’s Ken Rosenthal and Will Sammon.

No one is surprised the Sox will be sellers at the deadline. Their 23-52 record is the second-worst in the league, while the gap between them and the basement-dwelling Rockies shrinks as the eight-game losing streak unravels. The promotion of top prospects Chase Meidroth, Grant Taylor, Kyle Teel, Noah Schultz, and most recently Wikelman González signals that the youth wave is upon Chicago’s shores. To make room for the new era of Chicago baseball, the Sox need to say goodbye to their two most expensive players.

The Benintendi and Robert contracts won’t be easy to pawn off. Although he has recently heated up, Benintendi’s middling .246/.309/.444 slash line with 22 runs, 27 RBIs, and seven home runs doesn’t justify the $32.2 million remaining on his contract, which runs through 2027. His five-year, $75 million deal in 2023 broke a franchise record, but offers zero value to any acquiring team. Out of his six-year, $50 million agreement, Robert has roughly $40 million left spread over his two club options before he becomes a free agent. It’s doubtful any team would pony up that much, however, after seeing his .190/.273/.303 slash line, 25 runs, six home runs, and 28 RBIs this year. Trading for Robert is almost assuredly a playoff-push move for 2025 only, making any return for Robert wafer-thin.

Together, their contracts this year make up roughly 42% of the Sox’s payroll.

Incentivizing competitive teams to take on Benintendi’s and Robert’s deals may be challenging, but the Sox are willing to throw some change into the deal to defray the steep costs of taking on their contracts. Although no owner will say no to cash, some contracts simply aren’t worth the cash or roster space. Benintendi has a better chance of attracting teams’ attention despite his recent injury struggles, while Robert might have a much harder time garnering interest with his dramatic decline in the last two years.

Although neither of them generate enough reliable offense, Benintendi and Robert’s absences spell more losses than wins. Without their most impactful veterans, the Sox would walk an even finer line of being the worst team in the league for the second straight year. Even with a deep farm system, the Sox don’t have enough talent in their organization to guarantee they’ll break 45 wins with their two veterans.