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Cubs End The 2025 Season Where They Started: Short Of The Brewers

Brewers win Game 5 in Milwaukee, Blackhawks start the season with fire, and more

GOOD MORNING, CHICAGO FANS

Hello, offseason, my old friend. The Cubs ALMOST pulled off the miracle NLDS comeback but ultimately fell short against their biggest rival.

Welcome to that time of year. The stare-into-the-abyss, sketch-out-trade-proposals, try-to-be-optimistic-but-feel-pessimistic, watch-old-highlights-of-the-glory-days, refresh-social-media-for-offseason-news time of year. It’s our trusted companion and enemy.

It really was a great year to be a Cubs fan. 2026 will be even better!

If you enjoy the Windy Conditions newsletter, forward this email to the Chicago sports fans in your life. They can subscribe here.

CHICAGO BEARS

2-2

4TH IN NORTH

MONDAY NIGHT FOOTBALL VS. COMMANDERS TONIGHT

This game means more.

Caleb Williams’ homecoming was ruined last season when the Commanders pulled off the Hail Mary victory. This is redemption for him. For Tyrique Stevenson. For the entire organization that lost 10 straight games after that backbreaking moment.

We get Round 2 of Caleb Williams vs. Jayden Daniels. The general opinion is that Daniels is clearly the better quarterback from the 2024 NFL Draft, but I disagree. His rookie season was stellar, but his offensive system was tailor-made to succeed. Whatever your opinion, watching them battle tonight and many times in the future will be can’t-miss TV.

This is a statement game. The Bears need to put the past behind them. The Commanders are a shining example of an organization that actually took a 180 with a new owner, general manager, head coach, and quarterback, and found success on the field. We need to see the new Bears.

Oh, and if you missed last week’s newsletter, I wrote about the upcoming schedule. Win this game and there is a GREAT path to a winning record. Stack some wins!

  • TJ Edwards and Kyler Gordon are back and will make their season debuts!

  • Theo Benedet will in fact start at left tackle

  • Grady Jarrett is out with a knee injury

Opened the IR windows for Austin Booker and Travis Homer to return to practice and potentially game action

SCHEDULE 📅 TONIGHT @ Commanders, SUNDAY vs. Saints

CHICAGO CUBS

PLAYOFFS

NLDS

NATIONAL LEAGUE DIVISION SERIES

L - BREWERS 7 CUBS 3 (GAME 2)

2 OUTS AND 1 TO GO

  • Another top of the 1st moment (Seiya Suzuki 3-R HR) was immediately wasted when Shota Imanaga gave up a 3-R HR to Andrew Vaughn (thanks, Sox)

  • Brewers scored all 7 runs with 2 outs

  • Cubs only managed 2 hits and 0 runs after the 1st inning

W - CUBS 4 BREWERS 3 (GAME 3)

FOUR SCORED AND SURVIVE AGAIN

  • Cubs reversed the trend by answering the Brewers’ 1-run 1st inning by seeing 53 pitches and plating 4 runs in the bottom half (most runs by the Cubs in a playoff game since October 12, 2017)

  • Michael Busch became the only player in MLB history to hit multiple leadoff HRs in a single playoff series

  • Brad Keller closed it out with a 4 out save!

W - CUBS 6 BREWERS 0 (GAME 4)

SHOWED UP FOR THE SHUTOUT

  • Cubs had their best offensive approach of the entire postseason with 10 hits, 6 walks, 3 homers, and a ton of hard hit balls

  • Ian Happ started the party with a massive 3-R HR in the 1st inning and hit 3 other missiles throughout the game that just fell short of the bleachers

  • Matthew Boyd came back with a vengeance and threw 4.2 impressive innings (6 K) before handing it over to the bullpen

L - BREWERS 3 CUBS 1 (GAME 5)

A FRONT ROW SEAT

  • Another year, another Brewers champagne celebration right in front of the Cubs’ faces

  • Brewers hit 3 2-out solo homers in a battle of the bullpens

  • Cubs had 2 on with 0 outs in the 6th and couldn’t score

STAR OF THE WEEK ⭐ Seiya Suzuki

4-for-17 (.235 AVG), 2 HR, 4 RBI

PLAY OF THE WEEK 🎥 Ian Happ 3-R HR

End of the Season

This Cubs team defied the odds from Day 1,

They acquired Kyle Tucker in the offseason and then placed their bets on outperforming projections. Somehow, it actually worked.

Despite Tucker vanishing in the second half, losing Justin Steele for the season, missing Shota Imanaga and Jameson Taillon for extended periods of time, getting zero return from 5-6 late inning reliever options, Wrigley winds suppressing offense, and a non-existent offense after June, the Cubs won 92 games and were 1 win away from the NLCS.

This was a step in the right direction in Jed Hoyer’s quest to build a champion.

By October, the makeshift pitching staff was holding onto threads with only two trusted starters, and the offense was missing reliable impact and big hits in clutch situations. The shortcomings in roster construction, second half performance, and injuries stopped them from going further. This team still needs to improve in every facet of the game.

90 wins was supposedly the benchmark; however, the Brewers should be the true measuring stick. Winning at an organizational level is on the horizon, but the Cubs haven’t arrived.

October baseball was back where it belongs at Wrigley. 2026 has to deliver even more.

CHICAGO BLACKHAWKS

0-2-1 (1 PT)

LAST IN CENTRAL

L - PANTHERS 3 BLACKHAWKS 2

CHASING THE CHAMPS

  • Frank Nazar buried a breakaway for the NHL’s 1st goal of the year

  • Artyom Levshunov struggled in the 1st period and committed 2 penalties

  • Spencer Knight impressed against his former team and kept the Hawks alive with 34 saves on 37 shots

L - BRUINS 4 BLACKHAWKS 3 (OT)

NOW THAT’S WHAT THEY CALL HOCKEY

  • Hawks stayed toe-to-toe with the Bruins in a high-energy game featuring 1st goals from Connor Bedard, Louis Crevier, and Andre Burakovsky

  • Nazar was robbed of the OT winner as both goalies turned in highlight reel saves

L - CANADIENS 3 BLACKHAWKS 2

PENALTIES ON PARADE

  • Hawks were a bit too feisty in their home opener - they committed 14 penalties and gave the Canadiens 10 power plays!!! They somehow killed 8 of them.

  • Sam Rinzel tied the game at 1 with his first NHL goal

  • Kaiden Guhle scored the game-winner with 15 seconds left during an onslaught in the Hawks’ zone

STAR OF THE WEEK ⭐ Frank Nazar

1 goal & 4 assists (5 points), 7 shots

PLAY OF THE WEEK 🎥 Sam Rinzel 1st NHL goal

Opening Day Lines & Pairings:

Donato-Bedard-Burakovsky

Teravainen-Nazar-Bertuzzi

Dach-Dickinson-Mikheyev

Foligno-Greene-Lafferty

Grzelcyk-Rinzel

Kaiser-Levshunov

Del Mastro-Murphy

  • Colton Dach moved up to the 1st line after Game 1, swapping spots with Ryan Donato

  • Alex Vlasic made his season debut in Game 2 and was paired with Sam Rinzel

Placed Landon Slaggert and Joey Anderson on IR to start the season, called up Ryan Greene, assigned Ethan Del Mastro to the AHL after Game 2

3rd youngest roster in the NHL to begin the season

Jason Dickinson has an upper body injury and may be out for a week

SCHEDULE 📅 M/W/F/SUN

CHICAGO BULLS

OFFSEASON

PRESEASON

W - BULLS 118 CAVALIERS 117

  • Dalen Terry sealed the win with a big block

  • Matas Buzelis scored a team-high 19 points

W - BULLS 119 CAVALIERS 112

  • Four guards put up double digit points (Tre Jones, Josh Giddey, Ayo Dosunmu, Jevon Carter)

  • Both teams lived at the free throw line and left easy points on the board (Cavs: 22/32, Bulls: 19/32)

L - BUCKS 127 BULLS 121

  • Ayo led the team with 22 points off the bench

  • This matchup was heated! Dalen Terry got ejected, Emanuel Miller lost part of a tooth, and Ayo got a cut above his eye

Matas Buzelis said he contacted Derrick Rose to ask about his mentality when he entered his second season in the NBA

Season Opener ➡️ October 22nd vs. Detroit

SAY WHAT?

“We're going to LA after Milwaukee.”

Craig Counsell before Game 5 of the NLDS

“Practice be a blood bath.”

Ayo Dosunmu on the Bulls reflecting their practice habits by fouling the Cavs a lot

“I'm gonna tell our guys it's the first inning every inning.”

Craig Counsell on the Cubs offense after Game 3

“It affected the way we played for sure.”

Pat Murphy on the Wrigley Field crowd in Game 4

“He's been our best player all year.”

Pete Crow-Armstrong on Michael Busch

“We almost stopped practice and sent everybody home today because Ayo took a charge.”

Billy Donovan on the Bulls’ emphasis on physicality during training camp

“They never boo a bum.”

Pat Murphy on Brewers fans booing Craig Counsell

“We go put more balls in play, we'll probably score more runs.”

Pete Crow-Armstrong on the Cubs’ struggling offense

“I can throw 100 [mph] right now.”

Carlos Zambrano on if he can still play

A CITYWIDE SALUTE

Tyrique Stevenson

With the Commanders game looming, the spotlight has been on Tyrique Stevenson all week long because of his mistakes in last year’s matchup.

He took the opportunity to be open and vulnerable with the media about how he has dealt with the aftermath of that Hail Mary. Not only has he gained a mature perspective on that moment and his whole career, but his play on the field has also taken a huge step this season. Watch him talk about it here:

MILD TAKE

Re-sign Kyle Tucker.

This may be my hottest take yet based on the discourse amongst Cubs fans over the last 3 months.

He had a .738 OPS and only hit 5 HRs in the second half of the season. Whether it was solely due to injury, mainly just a slump, or partially because of the pressure to perform in a new big market, it was a devastating drop-off for a team trying to play deep into October.

If we zoom out to the entire season, Tucker had a 4.5 fWAR (3rd on the Cubs), hit 22 HRs and stole 25 bases, and walked just about as many times as he struck out (87 BB to 88 K).

That type of player with lefty power, elite plate discipline, contact skills, and star-level production doesn’t come around too often. Owen Caissie could only dream of playing as well as Tucker in the big leagues.

This offseason, the Cubs will be faced with the same questions as last offseason: do they create spots for young players or do they “combine WAR” by acquiring a superstar? Letting Kyle Tucker walk accomplishes one of those goals but reverts the team back on the other.

Build around PCA. Build around King Tuck. He’s already here.

HITTING THE LINKS

Dan Wiederer - Bears’ Tyrique Stevenson is on a journey of self-improvement after Fail Mary (The Athletic)

Andy Martinez - How Cubs’ Drew Pomeranz went from unknown to key October bullpen piece (Marquee Sports Network)

Jesse Rogers - MLB playoffs: Why Wrigley Field is a hitter's worst nightmare (ESPN)

Scott Powers - Why the Chicago Blackhawks wear their numbers, 2025-26 edition (The Athletic)

Chicago Bears - Bears building momentum week by week | 1920 Football Drive | Chicago Bears (YouTube)

TWO MINUTE WARNING

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