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For the first time in major-league history, a team has reached the postseason after enduring three straight 100-loss campaigns. The Chicago White Sox have accomplished that unprecedented feat, but their work is far from done.
Securing the division title remains crucial for Chicago, as it would grant them a first-round bye and valuable rest ahead of a potential pennant chase. More importantly, several players must elevate their performance for the White Sox to reach their full potential and continue defying expectations.
Colson Montgomery's Critical Role
Shortstop Colson Montgomery has experienced a turbulent season. Despite hitting 31 home runs and driving in 87 runs, he is batting right at the Mendoza line with a .696 OPS and is tied for the MLB single-season record with 223 strikeouts. Over his last 15 games, Montgomery has slashed a dismal .082/.224/.122—numbers that are unacceptable for a player who had 23 home runs and a .771 OPS at the All-Star break.
With top prospects Caleb Bonemer and Roch Cholowsky waiting in the wings, Montgomery needs a strong postseason. The team's offense is starting to click, with Munetaka Murakami, Braden Montgomery, and Kyle Teel emerging from slumps. If Montgomery follows suit, it could be the final piece of a potent Chicago offense that could make noise in October.
Anthony Kay's Bullpen Transition
Anthony Kay has likely pitched his way out of the postseason rotation due to recent struggles, but he is expected to play a significant role out of the bullpen. In his last seven starts, Kay has posted a 6.54 ERA while averaging under five innings per start. Length has always been an issue for Kay, and he will likely serve as a bulk reliever for at least the first round. If the White Sox advance deep into the postseason, he might be used as a back-end rotation member. Even so, his role in 2027 is uncertain if Grant Taylor, Noah Schultz, or Hagen Smith make the jump from the bullpen to the rotation.
Bryan Hudson's High-Leverage Struggles
Bryan Hudson was once a reliable high-leverage arm for the White Sox, even sporting a sub-2.00 ERA at one point. However, since June, he has become a liability. Over his last 30 games, he has a 5.20 ERA. While he has walked just one batter in that span, his inability to keep the ball on the ground has cost Chicago some games. Hudson must regain his form for the White Sox to have a chance at a deep run.
Matthew Singer is a contributor for White Sox on SI. Before joining SI in 2026, he worked for Heavy as an MLB contributor and Cubs on SI. Singer holds a master's degree in sports journalism from the Walter Cronkite School of Journalism and Mass Communication at Arizona State University. He loves sports more than anything in the world.