Ex-GM's massive White Sox-Red Sox trade feels less plausible with every loss

The White Sox fought and clawed their way to a tough series split against the Guardians this weekend, and looked to head home carrying some momentum. Instead, the first two games against the Red Sox have been ugly. The White Sox have been outscored 13-1 in the series so far, and they’ll look to avoid being swept at home for the third time this season on Thursday. The Red Sox have largely underachieved so far in 2026 and the primary rumors have surrounded which players they might sell. But with Boston playing much better baseball over the past few weeks, the White Sox may only be hurting themselves at the upcoming deadline. 

Veteran pitchers Sonny Gray and Aroldis Chapman have been tied to the White Sox in rumors, and both make sense as veteran arms on short-term deals. The Athletic’s Jim Bowden, a former MLB GM, proposed a trade that would land both pitchers in Chicago a couple weeks ago, but would require a significant prospect haul going to Boston. However, the Red Sox are hot. They’re 10-2 in their last 12 games dating back to June 25th and they’re now within just three games of a playoff spot in the mediocre American League. For a team that came into the season with playoff aspirations, it may be the fuel they need to add instead of subtract at the trade deadline. 

In a vacuum, the White Sox losing a series to the Red Sox isn’t the end of the world, but it came at a very poor time, and a hot streak for Minnesota and Detroit as well have made both the AL Central and the American League as a whole much tighter. The number of teams looking to sell at the deadline is shrinking, meaning the supply is decreasing and demand is increasing. White Sox fans can expect to pay a pretty penny for impact talent. With the club reportedly unwilling to part with any top prospects, the majority of the help may come from within. 

The White Sox should be prepared to pay a premium for deadline pitching help

It’s not the news that White Sox fans want to hear with the team in a position to buy for the first time in several years, but Chris Getz has always maintained the importance of the long-term view over short-term success. I’d urge the White Sox, however, to remember the Baltimore Orioles as a cautionary tale. The Orioles had an excellent core of young talent that saw modest success, but the team always balked at the idea of trading prospects for young pitching. Just a couple years later, the Orioles have stalled, many of the prospects they hoarded didn’t pan out, and they have yet to find answers in their rotation. The last thing the White Sox need is to end up in the same situation. 

With a first overall pick coming up in less than a week and a new confidence in their player development system, the White Sox should feel good about their ability to replenish the talent in their farm system, and shouldn’t be afraid to deal from areas of strength to address needs. The markets are going to be competitive, and the White Sox need to step up. 

The exact number of buyers and sellers is not yet clear, and a few weeks remain before trade activity will significantly pick up, but the White Sox are doing themselves no favors by losing games to Boston and keeping this race close. Hopefully, Munetaka Murakami’s imminent return will give the lineup a significant boost and they’ll be able to carry some momentum into the break.

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