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Chicago Sports Report: Catch Up On The Latest With WBEZ’s Cheryl Raye Stout artwork

Chicago Sports Report: Catch Up On The Latest With WBEZ’s Cheryl Raye Stout

In the Loop with Sasha-Ann Simons

September 28, 2026

There’s so much happening right in Chicago sports on all fronts. For the first time in history, both the White Sox and Cubs secured their seats in the playoffs on the same day. The Bulls are about to begin training camp.

Speakers Sasha-Ann Simons, Cheryl Raye Stout, Meha Ahmed, Clare Lane, Hunter Manet

TopicsNews

SPEAKER_1 (0:00)

WBEZ is supported by Impact Grants Chicago, a women's collective giving organization celebrating its 10th year of grant making in 2027

Women pool their giving to fund $100,000 grants for vetted Chicago nonprofits and select the nonprofits through a rigorous application review process. Growing the membership increases the number of $100,000 grants. Join by December 31st at impactgrantschicago.org.

SPEAKER_2 (0:28)

Monday night football, everybody, that is going to be the stage for the Chicago Bears as they host the Philadelphia Eagles.

SPEAKER_3 (0:35)

Jarring news that Tyson Bajan is in concussion protocol.

SPEAKER_4 (0:39)

Fly ball right field, Conforto is there, ball game, Cubs win.

SPEAKER_5 (0:45)

Bannum gets it off, off the front iron, into the hands of Iriafin as time expires. And Washington outlasts Chicago for the wire to wire win.

Sasha-Ann Simons (0:56)

Hey Chicago, I'm Sasha-Ann Simons, and this is In the Loop.

Be sure to listen all the way through the podcast for a breakdown of the day's top local stories. But first, Chicago sports fans, are you keeping up? There's a lot to discuss, debate and cheer on right now when it comes to our home teams. Wild card baseball, here we come. The Cubs and White Sox kick off postseason play tomorrow after both teams clinched playoff berths on the same day for the first time ever.

SPEAKER_7 (1:31)

We wake up tomorrow, we got more baseball to play, so I think we're all just looking forward to the craziness that's about to ensue and keep it pushing.

SPEAKER_8 (1:39)

Honestly, I think proving a lot of people wrong has been fulfilling, at the start, it's not exactly what you planned, but being here now, it's amazing.

Sasha-Ann Simons (1:49)

Meanwhile, the Bulls are preparing for training camp, the Sky are wrapping up the regular season, and the Blackhawks are gearing up for their season opener. As I said, lots happening. So in this episode of The Pod, we called up Cheryl Raye Stout, WBEZ's sports contributor, to help us keep track in a rapid-fire sports roundup of sorts. We started with football. For those who may not have been following closely, I asked Cheryl to tell us what on earth happened to Bears quarterback Caleb Williams. Here she is.

Cheryl Raye Stout (2:16)

Well, last week, he injured his hamstring.

And he's out. He's not playing tonight. And that means that Case Keenum is going to get the snaps.

Sasha-Ann Simons (2:29)

Case Keenum. Okay. So as far as I understood it when you explained it last week, Case is the backup to the backup quarterback?

Cheryl Raye Stout (2:37)

Okay.

Meha Ahmed (2:38)

So tell us more.

Cheryl Raye Stout (2:40)

Tyson Bajant was taking out a concussion protocol yesterday, but he's not ready to start because Case Keenum took all the snaps in the preparing for this game.

It's going to be interesting because last year, when they played Philadelphia, they were able to do a lot against them. They ran against them. They were able to do a lot of things. But that's with Caleb Williams at the helm. With Case Keenum, he's not a scramming quarterback. So it's going to be interesting how Vic Fangio's defense will go attacking Case Keenum.

SPEAKER_2 (3:15)

Yeah.

Sasha-Ann Simons (3:15)

They're facing off against the Eagles tonight?

Cheryl Raye Stout (3:18)

Yes. The Philadelphia Eagles, like I say, Vic Fangio is their defensive coordinator and he will be dialing it up. The one thing that the Bears offensive line has to do is not have the pre-snap penalties that they had last week.

Sasha-Ann Simons (3:35)

Right. Let's pivot now from football to baseball, Cheryl, because there's lots happening there. Our baseball teams have officially made history. When was the last time both the Sox and the Cubs went to the playoffs? Not to mention qualifying on the same day.

Cheryl Raye Stout (3:49)

Well, it was 2021 and that was during the COVID time, so it's kind of like, it's kind of a moot point. But the previous one was 2008, when they were both in the postseason.

Sasha-Ann Simons (4:00)

Yeah, so it's been a while, and it's definitely a historic moment, for sure.

Cheryl Raye Stout (4:06)

It's fun. It's fun to see both teams. Everyone expected the Cubs to get where they're going. You know, they have the MVP of the National League, and Pete Crowe Armstrong.

They have Alex Bregman. They have a lot of players. And Alex Bregman came back after his face getting smashed, and he hit two home runs yesterday. And then you look at the White Sox.

And this is a young team that everyone's going, well, they lost 100 games the last three years. They came back resilient, young, and want to prove themselves. And they have a lot, you know, they've got Miguel Vargas. You've got, you know, a lot of players. Mooney, Amerikami, this young man is starting to hit again. The Japanese player, the pre-agent they signed at the Superstar's basement. Absolutely.

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