A little over a year ago, I wrote an article titled Drinking Too Much Kool-Aid that was taking a best case scenario, optimistic look ahead into the future of the major sports teams in Chicago. Well, since then, the Cubs made the playoffs, won a series against the Padres, and are currently in 1st place in the NL Central. The Bears made the playoffs under Ben Johnson and beat the Green Bay Packers in the Wild Card for their first postseason win since 2010. The Blackhawks, in their Centennial celebration year, have shown an improvement for a 2nd straight year, while also becoming the youngest team in the league for the first time since the ’08-’09 season. Last, but not least, White Sox have secured the #1 overall pick in this years draft and are currently .500 for the first time in 1,316 days. And well, the Bulls are the Bulls, not much good happening over there- but hey, they had just about every second round pick in the draft this year after the trade deadline (14) so there’s that.
Now that I’ve gotten your attention (or not, there hasn’t been a blog in almost a year and even then there were like 5 people reading these); Let’s drink the Kool-Aid together as we look ahead to a decade plus of success in the Windy City.
Cubs
2025: 92-70, Lost in NLDS to Milwaukee Brewers
2026 Prediction: 95-67, NLCS or World Series bound
At the time of writing this, the Cubs are 27-16 and sit atop the NL Central. They have currently dropped 4 straight, but are still 2.5 games ahead of the second place Brewers thanks to a 20-3 run. Despite not touching the ball the past few games, the Cubs offense this season has been a pitcher’s nightmare. The emergence of Moisés Ballesteros, Nico Hoerner playing like an MVP, and even the bats coming off the bench have come through with guys like Matt Shaw and Michael Conforto contributing in big ways. Even with PCA, Michael Busch, and Alex Bregman starting the year slow (and Suzuki on the IL for the start of the season), these guys are all starting to find their stride. As I mentioned, they have dropped 4 straight with the offense going a combined 5-58 with 3 runs scored in the last two games. However, this offense is too good to not snap out of this little slump. Baseball is a funny sport.
The offense and defense of this Cubs team are both elite, it’s the pitching that is cause for concern. The Cubs have 10 pitchers on the IL and can’t catch a break. Justin Steele was supposed to be nearing a comeback after coming off elbow surgery, but has faced a setback in his rehab. Cade Horton lasted only a few starts before needing Tommy John surgery. On top of that, Mathew Boyd was playing with his children and somehow needs knee surgery now. The starting rotation and bullpen are both in shambles right now- but have found ways to survive thanks Shota Imanaga bouncing back and Colin Rea stepping up. Although I was a bit sad to part ways with Owen Caissie this offseason, the acquisition of Edward Cabrera has been huge.
Jed has locked up this core for a few years with the recent extensions given to PCA and Hoerner. This team is special, the core is here, all that’s needed is some pitching depth (and maybe an investigation into the Cubs training staff). Look for the Cubs to trade for some arms and make a deep run in the playoffs in this year.
Bears
2025/2026: 11-6, Lost in Divisional Round to Los Angeles Rams
2026/2027 Prediction: 12-5, back-to-back NFC North Champs
For the first time since 2020, the Chicago Bears made it to the playoffs. As mentioned above, they won their first playoff game since 2010, too. Ben Johnson came in and changed the culture of this team. After watching Matt Nagy and Matt Eberflus for the past few years, this was a breath of fresh air. Kudos to Ryan Poles for going out last offseason and getting the coach this city needed. Ben Johnson went 11-6 in his first year as the Bears head coach and looking back on the season, it could have been better and worse at the same time. I say that because of course they could’ve won a few more games, however, I don’t think this team gets a whiff of playoffs with any other coach besides Johnson. The biggest difference between the 2024 and 2025 seasons was that it seemed the Bears were never out of it. They won the close games that would’ve gone the other way in years past, a big part of that being Caleb ‘Iceman’ Williams leading comeback drives late in the game.
While the Bears are losing a few of their key pieces from the ’25 offense (DJ Moore, Drew Dalman, Jaquan Brisker, Kevin Byard, and Nahshon Wright), I have no doubt in my mind that the Bears will be back in the playoffs, possibly making it further. Largely because of Ben Johnson’s offense- which should be just as good, if not better than last season. Although the defense relied heavily on turnovers last season, the offseason is not finished and the secondary should still be elite as long as guys are healthy.
One thing worth noting, the Bears had the fewest penalty yards called against them last year. 678 penalty yards called on Bears opponents where the NFL average was 871. Over the past 4 years combined, the Bears rank in ‘penalty yards called against opponents’ is the #1 fewest in the league. What’s worse is the ‘roughing the passer’ penalties. It is obvious to any fan who watches the games, but there are stats to back it up now. Opponent ‘roughing the passer’ penalties on Bears QBs are 7 total since 2022, or the 32nd most in NFL. Bears penalties on ‘roughing the opponent’s QB’ are 17 total, or second most in the NFL. There is more too it as well, but it looks like the league is against Chicago. Prove them wrong, Ben. Win regardless of the refs. Do it despite having NFL’s toughest schedule this year (8 of their 17 opponents were playoff teams). Give Chicago a Superbowl Shuffle in early 2027.
Here is the tweet referencing the “Bears Tax” as he puts it. There is a whole thread on how the Bears have been bent over by the refs since 2022-
BlackHawks
2025/2026: 29-39-14 (72 points), 8th in NHL Central Division, Missed playoffs
2026/2027 Prediction: 39-30-13 (91 points), Squeak into playoffs
The 2026 Draft Lottery gave the Blackhawks the #4 overall pick in this year’s draft. While they were hoping to get higher to secure one of Gavin McKenna or Ivar Stenberg, a top 5 pick is still great and fingers crossed it’s the last one needed for a long, long time.
The Blackhawks are a young team, and a young team that will have growing pains. For example, the defensive core has a lot of raw talent, but they lack experience. On the flipside, the Blackhawks powerplay kill was unbelievably good this year. Besides experience, this Hawks team lacks scoring. Connor Bedard (30G 45A) took another step up this past season and is well on his way to being a superstar, however, he is not enough. The team’s second leading scorer was Tyler Bertuzzi- who had a huge season with new career highs in goals (32) and points (58). But, what this team really needs are guys like Frank Nazar, Anton Frondell, Nick Lardis, and Artyom Levshunov to become stars. Other guys like Oliver Moore and Ryan Greene provide good depth and are very solid players, but the system is still packed with prospects knocking on the door of the NHL. It is time for Kyle Davidson to make some decisions on his young talent pool and potentially make a big trade. They have the capital to go and get Bedard a star linemate and really accelerate this rebuild.
With the addition of a star to play besides Bedard, Frondell or even Roman Kantserov could step up and be a 30 goal scorer. Roman Kantserov, who led the KHL with 36 goals, just signed his three-year, entry-level contract. He is the first 21 year old to lead the KHL in goals since Kirill Kaprizov, who is a star in Minnesota.
The right draft pick, splash trade, and some more developing, this young core could lead to the Blackhawks in the playoffs as early as next year. Right now, my completely unbiased take is 3/3 for Chicago teams making the playoffs in their current/upcoming seasons. Wanna take a guess at what I am going to say about the White Sox, who currently hold the 5th Wild Card spot???
White Sox
2025: 60-102, Missed playoffs (obviously)
2026 Prediction: 76-86, Barely miss playoffs, (2027 is the year)
Depending on how weak the American League continues to play, the White Sox may find their way into a Wild Card game, but it is doubtful. However, this rebuild has been heading in the right direction ever since the Garrett Crochet trade. They currently sit in 2nd place in the AL Central and have a 16.1% chance of making the playoffs- so you’re telling me there’s a chance? You can see the core taking shape with guys like Davis Martin, Noah Schultz, Colson Montgomery, Munetaka Murakami, Chase Meidroth, and Kyle Teel. The last rebuild saw highly touted prospects like Yoan Moancada and Luis Robert. Everyone was excited only for their window to last two seasons- I believe this time around is different. I believe the window is going to be open a lot longer. Especially if guys keep progressing and performing the way they do while also seeing reinforcements from the farm like Braden Montgomery, Caleb Bonemer, and Hagen Smith.
There are 29 other MLB teams kicking themselves for not giving Murakami an offer. A pure 3 true outcome king who currently has 15 bombs and a .900 OPS. He has been a huge surprise- not because of lack of talent, but because of being undervalued by literally everyone except the White Sox. He needs to be locked up for a long time on the Southside. Another player that has turned heads and should be signed to a long extension is Colson Montgomery. A year ago he was sent to the White Sox Arizona complex for a “reset”; Fast forward one year and he is on a 7+ war 162 pace that would see 45 bombs, 125 RBIS and an .825 OPS. On top of that, he is playing ELITE defense at shortstop and is second in all of baseball with +6 outs above average at the position.
Let’s not forget about the breakout from Miguel Vargas and Sam Antonacci. Miguel Vargas is the second most valuable third basemen in the league with a 1.6 WAR, only behind Max Muncy (2.0). Antonacci may not have the home run pop like the rest of these guys mentioned, but he is a gritty, hard-nose player who grinds ABs and would probably run through a brick wall if you asked him. It almost looks as though he has been the spark for this White Sox team.
The White Sox future is definitely bright considering they have 5 top 100 prospects in baseball AND the #1 pick (Roch Cholowsky). Crosstown classics are going to be electric.
Chicago is a baseball town.
There are many more bright spots, topics, and players to cover for each of these teams. While it has been a while since the last article, look for more coming up as things are getting exciting in Chicago. Maybe I should start making 6 second videos instead because most people’s attention span is too fried to read this whole thing.
Always Next Year 
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