June 23, 2025 5:00 am EDT
A popular sports radio discussion topic in Chicago these days is “Which team will win a title next?” I say sports radio because they have to find something to talk about to fill the time. In real life, people might just say, “No one, dummy,” and move on to more uplifting topics, such as real estate taxes and politics.
As you might’ve noticed, the state of Chicago sports hasn’t been great lately. The local sports teams are coming off the worst year in modern history, highlighted by a record-setting 121-loss White Sox season and a Bears team that lost 10 in a row.
Chicago’s identity has never quite been “the city of champions,” but the last few years have really tested the patience and the sanity of the fans. There’s only so much Matt Eberflus and Jerry Reinsdorf one can take.
But 2025 is off to a promising start, well, at least for two teams.
As of this writing, the Cubs are in first place in their division and have the best record in the National League. They’ve got the power and the speed, though the pitching might need an upgrade before the trade deadline. Still, this is a legitimate team that should win 95-plus games. As a bonus, using a set of recent data, Neil Paine recently suggested the Cubs are one of five teams that should — in theory — win the World Series this year.
The Bears finally (or seemingly, I suppose) made a good coaching hire by landing former Lions offensive coordinator Ben Johnson. While hope usually springs eternal before training camp annually for Bears fans, it’s certainly possible this is a budding playoff team.
As for the remaining teams…
Though still in last place in the American League, the White Sox are hanging their collective hats on being less embarrassing. There’s reason for muted optimism, namely that some of the prospects acquired in recent trades have begun to show up and produce for the big-league team. And oh yeah, the Sox added a Pope and a potential new controlling owner. Also, the Rockies are threatening to make the 2024 White Sox team an afterthought outside of Chicago.
The Blackhawks have Connor Bedard and other young, talented hockey players, but haven’t taken a step forward in terms of actually winning games, which is the preferred result of a rebuild.
The Bulls continue to strive for mediocracy. They just missed out on Cooper Flagg in this year’s draft lottery and seemed destined to finish once again in ninth place in the East.
The Sky look positively White Sox-ish this season with its skewed results against good WNBA teams. Angel Reese and Kamilla Cardoso might really be the second coming of Jerry Krause’s interesting, but ultimately ill-fated, Tyson Chandler and Eddy Curry idea.
Which leads us back to our original question: Which Chicago team will win a championship next?
We found some odds for that.
For this exercise, The Athletic poked around and got some hypothetical numbers. Remember, odds are just a way to understand expectations and outcomes.
So if you wanted to put money on which local team (we’re not including the MLS Fire or NWSL Stars in this exercise, nor do they deserve much consideration in it right now) wins a title next, what kind of odds could you get?
BetMGM’s trading strategy manager, Hal Egeland, is bullish on the Cubs and puts them at -190 as the favorites. The Bears come in second at +220. After that, we’re dealing in long shots with the Blackhawks (+2000), the Bulls (+2500) and the White Sox (+6600). (Disclaimer: BetMGM is the exclusive betting partner of The Athletic.)
“The Cubs edge out the Bears in (hypothetically) who will win the next Chicago championship,” Egeland told The Athletic. “Predicting future success is purely speculative, but the Cubs and Bears seem the most dedicated to remaining competitive at this point. The Cubs have a solid core, and it’s hard to imagine, in my opinion, that they wouldn’t sign Kyle Tucker after trading for him. The Bears have the No. 1 overall pick in quarterback Caleb Williams. We expect to see improvement from him and his new offensive line this season.
“The Bulls have pieces, but the NBA is reliant on having a star player, and until they get a top-of-the-line guy, they’ll stay where they are. The White Sox are far away and will need development from prospects to become competitive again, giving them a longer timeline. The Blackhawks have Bedard but still have quite a lot of work to do before becoming Stanley Cup contenders.”
DraftKings director of sports operations Johnny Avello didn’t go as crazy with the underdog odds, but his order is exactly the same, with the Chicago Sky thrown in too.
Avello has the Cubs at +220, followed by the Sky at +350. Then come the Bears at +400, the Blackhawks at +600, Bulls at +1000 and the White Sox at +1500.
“The Cubs lead the pack, with a legitimate chance to contend for a title as soon as this season,” Avello told The Athletic. “While the Sky, Bears and Blackhawks may seem further from championship contention, each team is building toward a brighter future. The Bulls and White Sox are currently long shots, but it’s worth remembering how unpredictable sports can be — team fortunes can turn quickly. That’s why even the White Sox, coming off one of the worst seasons in MLB history, would still be listed at +1500.”
The pecking order is pretty clear at the top, though I might juggle the bottom teams a little bit.
Let’s say I put out my own shingle as an oddsmaker like my fellow Steubenville native Jimmy “The Greek” Snyder, who actually started with a real office in our hometown with “B&F Commissioner” on the door. B&F stood for baseball and football.
I’d start with the Cubs -110 because they actually have a shot of winning it all this season. They have the sixth-best odds on BetMGM as of June 20 at +1300. I don’t know if I share Egeland’s optimism about the Cubs signing Tucker, but I think “win-now mode” is here for the next five years and if chairman Tom Ricketts gets his way in the upcoming labor battle with the players, we might see even more restrictions on top spenders like the Dodgers, Mets and Yankees, thus evening the field for the less-profligate Cubs owners.
Next, I’d go with the Bears at +400. If Williams can pilot Johnson’s offense, they’re a legitimate threat, and the NFL is the one league where you can make a quick jump from also-ran to legit contender. Johnson is the most accomplished assistant coach the Bears have hired since Dave Wannstedt, and I think he’ll have a better run in Chicago. If Johnson can make GM Ryan Poles look smarter and Williams play better, they’ll speak of him in Ditka-esque terms in the city.
After that, it’s really a coin flip, right? I’ll go with Blackhawks +750 (at least they have a star in Bedard) and then the White Sox +1200, the Sky +1500 and the Bulls +2500.
Remember, this isn’t winning a title sometime in the future, it’s being the first of these six teams in Chicago to do it. The Bulls and the Sky have easier paths to the playoffs, but winning a title seems almost impossible with their rosters and current draft assets. The Bulls, for example, have the third-worst odds to win a title in 2026 currently at DraftKings, at +40000. Matas Buzelis is a nice young player, but this isn’t an organization that’s really serious about winning it all. I’m not getting many good vibes about the Sky, though I do think Reese can be a Joakim Noah-like figure for the franchise.
Lastly, while I wouldn’t exactly invest in White Sox futures, I think they have a better shot of winning another one than either the Bulls or the Sky right now. GM Chris Getz has made some smart hires, and the prospects look promising. By the time Justin Ishbia takes over, this town might still be in a title drought, and the Sox could be ascendant.
And hey, depending on your belief system, they just might have God on their side. I might bet on that.
(Illustration: Demetrius Robinson / The Athletic; top photos: Matt Dirksen / Chicago Cubs, John Fisher / Getty Images, Bob Frid / Imagn Images)
Jon Greenberg is a columnist for The Athletic based in Chicago. He was also the founding editor of The Athletic. Before that, he was a columnist for ESPN and the executive editor of Team Marketing Report. Follow Jon on Twitter @jon_greenberg
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