Coulson Montgomery's breakout has the White Sox fanbase buzzing. A late-season surge across 71 games featuring 2.6 WAR signals a ceiling that could resemble Cory Seager territory, with power at short and a path to future corner events. The episode maps how Montgomery, Braden Montgomery, and Kyle Teal could anchor a rebuilt lineup while weighing Lenin Sosa as a potential trade chip and the value of extensions.

The discussion dives into roster construction, trade markets, and the delicate balance of cost vs upside as the organization plans for 2026. It also highlights Robert’s uncertain future and the chance the Sox pursue a meaningful, economical upgrade that compounds Montgomery’s rise with real-wins potential in the near term.

Chicago White Sox drop a 3-1 decision to Baltimore, swept in the series as nine games remain and the club sits at 57-96. Still, Meidroth’s 13-game hitting streak and Teal’s big homer offer real signs of life, with Benintendi contributing and the bullpen stabilizing behind Wilson and Taylor. Front office talk centers on a 2026-27 plan anchored by Luis Robert Jr. and in-house depth, aiming for growth and a hopeful rebuild arc rather than quick fixes.

In keeper and dynasty formats, a fresh crop of late-season waiver targets could redefine rosters next year. Garrett Cole anchors a plan to stash veteran aces who’ve shown durability, while Nathan Eovaldi and Joe Musgrove provide high-floor buys. Upside bets like Tristan Casas, Austin Riley, Luis Robert, and Shane McClanahan illustrate the payoff of health and spring momentum. Lesser-knowns such as Drew Thorpe and Chris Bubik close the arc, with offseason moves highlighted to unlock long-term value.