It’s been a rough stretch for Chicago sports. Will it get better?
As Chicago sports fans, we all know there have been plenty of stretches where the Chicago Sports landscape hasn’t been great. But even in those stretches, there’s usually at least one or two of the teams that win, or even dominate. The 1980s had the Bears, the 1990s had the Bulls, the 2000s saw the White Sox win a World Series, and of course, the Blackhawks were great in the 2010s and the Cubs broke their World Series drought.
But the 2020s? It hasn’t been great for really, well, any of the teams. Will things be getting better any time soon? Let’s take a look at the five major sports teams (apologies to the Chicago Sky, I hope Angel Reese brings them a championship but I don’t follow the league close enough to compare them) and rank them in terms of which teams are set up to succeed in the future.
5. Chicago Bulls
The Bulls are just stuck in NBA purgatory. If you don’t have a star, you don’t have anything. The Bulls were spinning their wheels in the mud the last few years and finally started blowing it up with DeMarr DeRozen exiting last year and the trade of Zach LaVine.
But until the Bulls have a potential building block, and I mean a true building block (sorry Coby White fans) that you can build around, there’s just not much here to think that AK can build this team into a contender. The Bulls are years away from being years away.
4. Chicago White Sox
The fact that this team isn’t last just tells you everything you need to know about Chicago sports. At least this team has torn it up and tried to replenish their farm system. After completely blowing their last rebuild, which ended with plenty of Major League talent, the White Sox are starting over, and after trading off several pieces, Baseball America now ranks their farm system as the 4th best in all of baseball.
These players need to develop both in the minors and then, of course, in the majors, but in three or four years, hopefully, the White Sox are competing once again.
3. Chicago Blackhawks
Connor Bedard. He’s good, and he’s still a teenager. Is he going to be the next Connor McDavid? Perhaps not, we will have to see what kind of season he puts together next season. When McDavid was 20, he tallied 100 points and led the league with 70 assists.
The Hawks haven’t exactly surrounded Bedard with a great supply of talent at this point, but it’s still very early in this version of the rebuild. We will see what the Hawks put together over the next couple of years but while they may not be where fans wanted to see at this point, the White Sox got the nod over the Bulls for having a direction and the Blackhawks got the nod over the Sox for having Bedard.
2. Chicago Cubs
The Cubs are without a question the team best set up to win now. The Cubs won 83 games last year and have added pieces like Kyle Tucker and Ryan Pressly and they have a solid stable of talent already and Craig Counsel is still one of the most respected managers in baseball.
The Cubs have a lot of solid players, but do they have enough top-end talent? Is Tucker going to be the guy to anchor the line-up and start pushing the Cubs towards competing with teams like the L.A. Dodgers?
I think the Cubs ceiling is good and can push for 90 wins, but can this team come together and become true World Series contenders? We will have to wait and see over the next couple of years to see if it all comes together.
1. Chicago Bears
Maybe the Chicago Cubs should be in the top spot, but I think the Bears are in the best shape to win big. The Cubs are going to be the better team in 2025, but I want to look at who is going to be in a position to win big in 2026 and beyond.
If you have the QB and the head coach right at the NFL level, you are a contender every year. I’m a believer in Caleb Williams and Ben Johnson, and I think those two gel this year and are in a position to truly contend in 2026.
The Cubs could take another swing with a trade or in free agency in the future that could make them World Series contenders, but as their roster is currently constructed, I don’t think their ceiling is that high. But for the Bears, if you think the Bears have the right QB and the right head coach, they are on the cusp of doing some big things on Sundays.