Welcome to the South Side Sports Roundup! Check back every month for the latest news and updates on everything South Side sports fans need to know.
The optimist’s view: A brighter 2026 is on the horizon in South Side sports
2025 is nearly in the books, and for once, there’s an argument that things are on the upswing.
The bar is low. There hasn’t been a lot to like about sports on the South Side over the last decade or two. Since the White Sox and Bears made championship appearances within sixteen months of each other between 2005 and 2007, those two teams have a combined 4-11 record in the postseason, with only the 2010 Bears advancing past the first round. The Chicago Sky gave us our biggest bright spot with their joyous run to a 2021 WNBA championship, but they’ve nonetheless had a winning record in just two of their last eight full seasons. DePaul basketball, now based on the South Side at Wintrust Arena, remains bleak.
Still, 2025 was a little different from previous disappointing seasons. A year after bottoming out and setting the MLB’s all-time loss record, the White Sox saw a promising young core materialize. The Bears, of course, have arrived well ahead of schedule, and have a chance to secure their first playoff appearance in five years.
So we’ll still keep close tabs on our Bears and Sox and Sky, because as bad as things have been for most of recent memory, we truly believe the news you read and the things you need to know will be more positive sooner rather than later.
Bears remain in playoff position despite loss to Packers
The Bears are not who we thought they were.
Unlike the 2006 Super Bowl squad that prompted former Arizona head coach Dennis Green to furiously spit out the now-iconic postgame declaration (“The Bears are who we thought they were!”) this year’s team had little in the way of expectations. These Bears weren’t supposed to be this good, sitting on a conference-leading 9-3 record entering last Sunday’s showdown with the Packers at Lambeau Field. Not yet, anyway.
The Bears lost that game, falling 28-21 on a freezing cold day in northern Wisconsin. While the outcome was disappointing, it was their first defeat since October 26. After five straight wins, three of which required an improbable comeback in the final two minutes, the breaks were due to go the other way sooner or later.
Even if they couldn’t pull it off again, they played the Packers tough. The vibes around the team are still positive, unlike most of the other twenty-nine losses to Green Bay (against just five wins) they’ve suffered since 2009. Adrian Canó is a Packers fan living in Woodlawn, but he’s enjoying “the sense of camaraderie” the Bears are bringing to Chicago.
“I also love how competitive the games feel now, it’s good for [all] those who grew up watching this rivalry,” Canó said. “I’m excited to watch Williams vs. Love for the next few years.”
The Bears’ record sits at 9-4 with four games remaining. Only twice in team history—the legendary 1985 and ’86 Super Bowl shufflers—have they won 14 or more games in a season. They’ve reached the 13-win mark twice, in 2001 and 2006, and went to the Super Bowl in the latter year. They most recently peaked at 12 wins in 2018, when their season ended on kicker Cody Parkey’s infamous “double doink” in the first round of the playoffs.
This coming Sunday’s game against the perpetually woeful Cleveland Browns is a critical chance to get to just one win shy of the 11-win plateau it may take to reach the playoffs. It’s shaping up to be one of the most exciting finishes to a season in recent memory. Matchups with the Packers, San Francisco 49ers, and Detroit Lions to conclude the campaign have the potential to entirely shape the NFC playoff picture.
The Bulls are who we thought they were
A surprising 6-1 start to the season had Bulls fans thinking that things might finally be different. Just read what we had to say in last month’s check-in.
A little more than a month later, they’ve dropped 13 of 16 games, and fans have settled back into the familiar feeling that nothing ever changes. The refrains are mostly things we’ve heard before, including this from longtime Bulls fan Zach Deitz.
“[It’s] more of the same. I wasn’t fooled by the 5-0 start… Any other team would have fired [team President] Arturas Karnisovas by now.”
Deitz, like many Bulls fans, has simply learned to accept the mediocre-or-worse place the team is constantly occupying in the NBA landscape.
“It’s sad and claustrophobic as a fan,” Deitz continued. “I want to say I’m apathetic, but in reality I’m just more assured in my own beliefs [about the team], because I knew this would happen.”
The Bulls sit 9-14 on the season after taking their seventh consecutive loss on Sunday, falling 123-91 in blowout fashion to the Golden State Warriors. It was their lowest offensive output of the season by a double-digit margin. But offense typically hasn’t been an issue. Eight Bulls starters are averaging double digits points per game. And yet again, as has often been the case this season, defense was their downfall. They’re twenty-seventh out of thirty NBA teams in total points allowed per game, and they also rank at or near the bottom of the league in steals and blocks.
A problematic lack of size is partly the culprit behind their ranking in blocks, and has also contributed to the Bulls getting killed in the rebounding department, ranking twenty-fifth in the league in that category. They’re the only team in the NBA that doesn’t have a single player listed as taller than 6’9”, and it shows.
The South Side does have at least one thing to be proud of in Morgan Park alumnus Ayo Dosunmu, who has taken his game to a new level with a career-highs of 15.2 points per game and 47.5% from deep, and more than 51% overall. Dosunmu also starred for three years at the University of Illinois Champaign-Urbana, where he was named an All-American in 2021. The same year, he led the Illini to their first NCAA Tournament #1 seed since 2005, though they were ultimately upset by the North Side’s own Loyola Ramblers in the second round.
Fans had better enjoy watching him now, however. He’s in the final year of his contract, and he’s due to command a whole lot more in free agency than the three-year, $21 million deal he’s finishing up now.
The Bulls only play in Chicago twice between now and Christmas, a two-game set against Cleveland and New Orleans on December 14 and 17.
Malachi Hayes is a Bridgeport-based writer and South Side native.