The Chicago White Sox have done something no other team has done in major-league history: make the playoffs after three consecutive 100-loss seasons. But the job isn't finished yet! Despite the incredibly successful season for Chicago, they still need to win the division for a deep playoff run.
Winning the division and earning a first-round bye would give the White Sox the rest they need to make a run at a pennant. But more importantly, there are some players who need to step up for the White Sox to reach their ceiling and continue to make the impossible possible.
Sep 16, 2026; Cleveland, Ohio, USA; Chicago White Sox shortstop Colson Montgomery (12) is hit by a pitch during the fourth inning against the Cleveland Guardians at Progressive Field. Mandatory Credit: David Dermer-Imagn Images | IMAGN IMAGES via Reuters Connect
It's been an up-and-down season for Colson Montgomery, to say the least. While he's hit 31 home runs and driven in 87 runs, he's right at the Mendoza line with a .696 OPS and tied for the MLB single-season record with 223 strikeouts.
In his last 15 games, Montgomery is slashing .082/.224/.122, unacceptable numbers 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 to have a good postseason
This team is starting to find its stride offensively, with Munetaka Murakami , Braden Montgomery, and Kyle Teel starting to break out of their respective slumps. If Montgomery does the same, it would be the final piece of a really good Chicago offense that could make some noise in the postseason.
Sep 22, 2026; Kansas City, Missouri, USA; Chicago White Sox pitcher Anthony Kay (18) pitches during the first inning against the Kansas City Royals at Kauffman Stadium. Mandatory Credit: William Purnell-Imagn Images | IMAGN IMAGES via Reuters Connect
While Anthony Kay has likely pushed himself out of the postseason rotation due to his horrible play of late, he will likely have a big role out of the bullpen.
In his last seven starts, Kay has a 6.54 ERA, averaging under five innings per start. Length has always been Kay's issue, and now he will likely be 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 member of the rotation.
Even so, his role in 2027 is in jeopardy if Grant Taylor , Noah Schultz, or Hagen Smith make a jump to the rotation from the bullpen.
Sep 23, 2026; Kansas City, Missouri, USA; Chicago White Sox starting pitcher Bryan Hudson (60) throws a pitch in the first inning against the Kansas City Royals at Kauffman Stadium. Mandatory Credit: Peter Aiken-Imagn Images | IMAGN IMAGES via Reuters Connect
Bryan Hudson was once considered to be a reliable high-leverage bullpen arm for the White Sox. At one point, he had a sub-2.00 ERA. However, since June, he has been a liability for Chicago.
In his last 30 games, he has a 5.20 ERA. While he's walked just one batter over that span, his inability to keep the ball on the ground has cost the White Sox some games. He will need to pick it up again for the White Sox to have a chance at making a run.
This article was originally published on www.si.com/mlb/whitesox/onsi as The 3 White Sox Who Have the Most to Prove This Postseason .
