The Chicago White Sox have already pulled off something no major-league team had ever done before: reach the playoffs after three straight 100-loss seasons. But even with that breakthrough in hand, there’s still unfinished business if they want this thing to turn into a real October run.
A division title would change the shape of everything for Chicago. It would bring a first-round bye, the kind of breathing room a team can use to reset and line up for a pennant chase.
And beyond the team goals, there are a few players whose postseason is about more than just advancing. For them, this is about proving they can handle the moment.
Colson Montgomery sits near the top of that list. His season has been a roller coaster: 31 homers, 87 RBIs, but also a .696 OPS and a share of the MLB single-season strikeout record with 223.
The recent stretch has been especially rough. Over his last 15 games, he’s hit just .082/.224/.122, a brutal slide for a player who went into the All-Star break with 23 home runs and a .771 OPS.
With Caleb Bonemer and Roch Cholowsky waiting as top prospects, Montgomery needs to deliver now if he wants to be part of Chicago’s next step.
That matters even more because the White Sox offense is beginning to come alive around him. Munetaka Murakami, Braden Montgomery, and Kyle Teel are all starting to shake off their slumps. If Colson Montgomery joins that group, Chicago suddenly has a lineup with enough punch to matter in October.
Anthony Kay is in a different spot, but his postseason importance is still real. He has probably worked his way out of the playoff rotation after a rough stretch, and he’ll likely be asked to help out of the bullpen instead.
In his last seven starts, he’s posted a 6.54 ERA and hasn’t gone five innings per outing on average. That kind of length issue has been a theme, and for now it points to a bulk-relief role in the first round.
If the White Sox keep rolling deeper into the postseason, he could still end up back in the rotation mix toward the back end.
Even his long-term place with the club isn’t settled. By 2027, his role could be in trouble if Grant Taylor, Noah Schultz, or Hagen Smith make the jump from the bullpen to the rotation.
Then there’s Bryan Hudson, who has gone from trusted late-inning option to a pitcher the White Sox can’t afford to keep leaking runs with. He once carried a sub-2.00 ERA and looked like a dependable high-leverage arm.
Since June, though, the bottom has fallen out. Over his last 30 games, he’s got a 5.20 ERA, and while he has walked only one batter in that span, his trouble keeping the ball on the ground has hurt Chicago in games it needed to finish.
If the White Sox are going to make a serious run, Hudson has to find that old form again.
In Other News...
White Sox Prospects Suddenly Face Bigger Questions After A Brutal 2026
The White Soxs prospect watch has taken a rough turn now that the 2026 minor league season is over, and a few of the organizations more notable names left the year with more questions than answers. Right-hander Tanner McDougal spent the season dealing with an injury and a role change, while infielder Jeral Perez had a harder time than expected adjusting to Double-A pitching, two developments that complicate the path the club had hoped to see from both players.
Christian Oppors season added another layer to the concern. The left-hander battled control problems and was eventually demoted, a setback that only deepens the uncertainty around his future role. For a farm system that needs progress, the issue now is not just who struggled in 2026, but which of these prospects can still put themselves back on track inside the White Sox organization. [Read more 🡒]
Colson Montgomery Just Reached A White Sox Milestone Nobody Wanted
Colson Montgomerys rookie season has delivered plenty of loud contact and enough production to keep the White Sox intrigued, even as one particularly unforgiving number now sits at the center of his year. The shortstop set a new club mark for strikeouts in a season, edging past a record long associated with Adam Dunn, while still giving Chicago real value with his power at the plate and steady work in the field.
Montgomery has hit 31 home runs and driven in 87 runs, good enough to rank among the American Leagues better power bats, and his defense has been a plus as well. His plus-10 fielding run value and top-tier outs above average show why the strikeout total does not tell the whole story, even if the milestone itself is the kind nobody in a rebuild wants to celebrate for long. [Read more 🡒]
White Sox Mourn A Pitching Voice Fans Will Never Forget
The White Sox lost one of the most recognizable voices in their modern baseball history with the death of Don Cooper at 70. A fixture in the organization for 33 seasons, Cooper spent 18 years as the clubs major league pitching coach and became one of the defining figures behind a generation of White Sox arms, building his reputation through relentless teaching and a presence that players and fans alike came to know well.
Coopers path to that role started with a brief big league playing career before he moved into coaching, where his influence only grew. For White Sox fans, he was more than a coach on the bench or in the dugout; he was part of the teams identity for years, and his long run in Chicago left a lasting imprint on the pitchers he helped shape and the organization he served. [Read more 🡒]