The Chicago Cubs’ 2026 run is officially in the history books, and let’s just say the vibes were a total rollercoaster. For the second year in a row, the team secured an NL wild-card spot only to get sent home early. This time, they were swept by the Padres in the first round. It’s giving major frustration after a season that started with so much promise.

The good vs. the chaotic

Real talk: this team had some electric moments. Between two different 10-game winning streaks, they hit an MLB-best 27-12 start. They led the majors in OPS and position-player WAR, and Pete Crow-Armstrong basically had a god-tier season—he’s looking like a lock for NL MVP. But then, the pitching staff had the worst WAR in the entire league. Not great, Bob. They blew 34 leads and finished the year 17-22 after mid-August.

The free agency scramble

The roster is looking thin heading into the offseason. Right fielder Seiya Suzuki and left fielder Ian Happ are both hitting free agency. Suzuki has been solid, putting up a career-best 5.1 WAR, while Happ struggled at the plate as a right-handed hitter. The front office is likely to prioritize keeping Suzuki, but the competition will be stiff. If they walk, the team might turn to internal prospects like Pedro Ramirez or Matt Shaw to fill the gaps.

Pitching in crisis

The pitching situation is honestly the biggest L of the season. Injuries plagued the staff, and the team’s strategy of hunting for bargain, high-risk pitchers clearly hit a ceiling. With several key arms—including Gausman, Imanaga, and Peterson—entering free agency, the rotation is basically up in the air. The front office needs a massive overhaul here to stop relying on quick fixes and start building a real system.

Why it matters

Jed Hoyer is now six years into his run leading baseball operations, and the team hasn't sniffed an NLCS or a division title yet. Compared to the previous regime’s track record, the current trajectory is falling short. With the Brewers dominating the division by 14 games this year, the pressure is officially on to stop rebuilding and start winning. It's time for the front office to prove they can build a sustainable contender, or the plot thickens for their job security.