One of the worst feelings that Chicago Cubs fans have had to grapple with since around 2019 is the feeling that the team was incomplete. Since winning the World Series in 2016, most offseasons could be characterized by a lack of spending and half measures well below what a big-market team should be capable of. Even last offseason, with the trade for one year of a superstar in Kyle Tucker, still felt one or two pieces short of being a truly great assembly of talent by Jed Hoyer. Tucker, too, came with the looming dread that the Cubs wouldn't pay up to retain his services beyond 2025.
The reliance has been on exceeding expectations and players taking steps forward to get results. It's why the Cubs missed the postseason two years in a row in 2023 and 2024 despite showing promising signs. In 2025, one more quality starting pitcher and/or another bat like, say, Alex Bregman, might've been the difference between an NLDS exit in Game 5 and a longer playoff run. Bregman, in particular, was a painful miss, with just about everyone in the organization believing he was the final piece they needed.
For once, though, the impending arrival of Opening Day 2026 feels different. Instead of leaving fans second-guessing decisions and deals, or the lack of them, the Cubs put the foot on the gas and silenced their increasingly vocal and justified national critics. Expectations are high again, and everyone around this team knows it.
This time, they went the extra mile for Bregman, signing him to the highest AAV in franchise history with a five-year, $175 million contract with deferrals. In trading Owen Caissie for Edward Cabrera, they finally added a starting pitcher with real swing-and-miss stuff in his game, albeit with real injury risk. They also rebuilt a bullpen nearly from scratch, spending around $30 million in total at a spot where Hoyer and company have often just relied on a couple of veterans and an ocean of reclamation types. The bench even looks better, even if Tyler Austin is down for "months" with an injury. The statement was clear to players and fans — winning the division won't cut it, it's time to push for a ring.
The impact of those moves has already been felt, from Bregman already getting to know the minor leaguers and spending a lot of time with young star Pete Crow-Armstrong to Cabrera turning heads in camp with his mix of velocity and wicked stuff. Team USA's last two exhibition games also featured a pair of Bregman homers, giving a taste of what the career 125 wRC+ third baseman can provide. These are the guys fans want to watch, and not just because they help the chances of postseason baseball go up. Not only that, but both have already fully bought into the organization.
Alex Bregman hits his second home run for Team USA 🔥pic.twitter.com/GI95JvcNTP
— Marquee Sports Network (@WatchMarquee) March 4, 2026
After finishing 2025 a game way from the NLCS, the Chicago Cubs needed an aggressive offseason.
It's the kind of offseason a 92-win team deserved. 2024 was a disappointment for many reasons, both because 2023 seemed like a step in the right direction and because the arrival of Craig Counsell seemed to be a declaration that it was time to win again. It forced 2025 to be a "prove it" year for the roster and the front office, where real changes could've been the consequence. The added pressure made the playoff run a confidence booster, showing that this team, carried by veterans like Nico Hoerner and Ian Happ, and breakout young players like PCA and Michael Busch, was capable of great things.
In a sense, they've now done the hard part. The rebuild that began with the 2021 sell-off of the World Series core and endured multiple years of stagnation is over. Maybe they waited a bit too long and missed on too many good players in the meantime, but by going in now, right after last year's success, the front office has given a big vote of confidence in the players and a big indicator to fans that, pun intended, this will be a season worth investing in.
This Opening Day now feels like the start of a new era. A new core is mostly locked in for the long haul, a new face of the team has emerged in PCA, and the wave of top prospects has mostly been sorted through to find the best mix of talent from the players they accumulated. In spending for Bregman, Cabrera, and the bullpen, they've answered that final, dreaded question of "if not now, then when?"
Make no mistake, there will still be bumps in the road and moments of lackluster baseball in the 162-game marathon. Right now, though, the vibes are good, and the Cubs have given fans little reason to worry that enough wasn't done to make this team the best it can be.
