Chicago White Sox Playoff Berth, and PCA Joins the 40-40 Club

Two Chicago baseball teams woke up in October territory on the same Friday morning, and one of them lost 121 games two seasons ago. The Chicago White Sox playoff berth is the least likely sentence anybody has typed about this sport all year, and four miles north Pete Crow-Armstrong just finished a 40-40 season that dragged the Cubs into the NL Wild Card. Same city. Same weekend. Completely different kinds of impossible.

I have been doing this long enough to know that most baseball seasons hand you one story worth telling your kids about. This one handed Chicago two, plus a strikeout record hanging by a thread and a goodbye to a man who spent two decades teaching pitchers how to breathe.

How the Chicago White Sox clinched a playoff berth after three 100-loss seasons

Start with the arithmetic, because the arithmetic is the whole story. From 2023 through 2025 the White Sox piled up more than 300 losses. Three straight seasons of triple-digit defeat. Nobody entering this spring had them anywhere near a bracket, and I mean nobody, including the people who work there.

checked the almanac: the 2024 white sox lost 121 games, the most in modern major league history, one more than the 1962 mets managed in their first miserable summer. that team is not a punchline from some distant era. that team was two years ago.

And now they are in. The reporting out of the South Side frames the way they clinched as a first, something the league has not seen done quite this way, and I will let the record keepers sort out the exact wording. What matters to me is the shape of it. Rebuilds are supposed to be a five-year tax bill. You take the beating, you stockpile arms, you tell the fan base to be patient while you sell them nine-dollar beers to watch a Triple-A lineup. The Sox were supposed to be a 2027 story at the earliest.

They skipped a grade. Whether the rebuild ran ahead of schedule or the American League left a door propped open is a debate for the winter, and honestly it is a boring debate. Every October team gets in through some combination of being good and being lucky. What you cannot fake is showing up in late September with games that matter after three years of being the sport's designated cautionary tale.

They host Colorado at 7:40 ET on Friday night. Guaranteed Rate, or whatever the sign says this year, is going to be loud in a way it has not been since Cooper was in the dugout. More on him in a minute.

Pete Crow-Armstrong 40-40: the Cubs season in one stolen base

Over on the North Side, Crow-Armstrong swiped his 40th bag against Miami to pair with 45 home runs. That is the whole ballgame for the Cubs, who officially punched their NL Wild Card ticket and did it largely on the back of one center fielder having the year of his life.

Here is why the number lands the way it does. Power and speed both peak young, but they almost never peak in the same body in the same summer, because the swing that produces 45 homers is usually attached to a guy who does not want to risk his hamstrings on a 3-2 count. The list of men who have done both is short enough to read in one breath.

Note the homer column. Crow-Armstrong's 45 is second on that entire list, behind only Soriano's 46 in 2006, and he got there while playing the kind of center field that used to be the entire scouting report on him. He came up as a glove. He leaves this season as an MVP-caliber bat who happens to also be a glove.

That is the part Cubs fans should sit with. The defense was never the question. The question was whether the bat would ever be more than a nice complement, and the answer arrived all at once, in a season where the Cubs needed exactly that and had no obvious backup plan. Franchise cornerstone is a phrase people throw around in June. This is what it actually looks like in late September.

The Cubs play a doubleheader at Fenway on Friday, first pitch at 1:06 ET and the nightcap at 5:36. Two more looks at him before the calendar flips to the part of the year he has never seen.

Colson Montgomery and the single-season strikeout record

One whiff. That is where White Sox shortstop Colson Montgomery sits, 222 strikeouts against Mark Reynolds' 223 from 2009, with the last weekend of the season in front of him.

The context matters more than the number. Reynolds set that mark in a season where he also hit 44 home runs, which is the deal you used to make: I will miss a lot, you will pay for the ones I do not miss. Since 2009 the league strikeout rate has climbed almost every single year. Velocity went up. Sliders got nastier. Bullpens turned into six-inning relay teams of guys throwing 98. Four hitters were on pace to pass Reynolds at some point this season, and Montgomery is the last man standing at the finish line.

So do not read this as a shaming exercise. A record that four different players nearly broke in the same year is not an indictment of one hitter. It is a weather report on the sport. Reynolds' 223 stood for seventeen years because it was an outlier. It is about to fall because it stopped being one.

And Montgomery is going to take those at-bats in games that matter for a playoff team, which is a sentence nobody in Chicago expected to write about anything this April.

Don Cooper's legacy with the White Sox

The late White Sox pitching coach hated the word legacy. His words, not mine: "I'm not looking to f---ing create a legacy. I just want to do what we got to do."

He got it done anyway, for the better part of two decades on the South Side. Cooper was in the dugout for the 2005 World Series title. He was there for Mark Buehrle's perfect game in 2009 and the no-hitter before it. He was there when Lucas Giolito rebuilt himself from one of the worst starters in baseball into one of the best, and threw a no-hitter of his own in 2020. Different eras, different arms, same fingerprints.

That is the job. You do not get a plaque for teaching a 24-year-old how to repeat his delivery in August. You just get the twenty years of pitchers who could. The White Sox reaching October this season has nothing directly to do with him and everything to do with the kind of place he spent his life helping build.

What to watch this weekend

Three things, all of them in Chicago's orbit.

Crow-Armstrong gets two games at Fenway in the Friday doubleheader, and every plate appearance now is a chance to put daylight between himself and that 40-40 line. He is at 45 homers. Forty-six would tie the highest total anybody has posted in a 40-40 year.

Montgomery needs one swing and miss. It will happen, probably early, probably on a slider down and away, and the record will belong to the new normal instead of to 2009.

And the White Sox host Colorado on Friday night as a playoff team, which is the part I still have to say out loud to believe. Three years, 300-plus losses, one summer that rewrote all of it. Baseball does not usually let you off the hook that fast.