After watching the Milwaukee Brewers clinch back-to-back NL Central titles in 2023 and 2024, the Chicago Cubs made a bold move to shift the balance of power. They brought in All-Star outfielder Kyle Tucker, aiming to not only close the gap but reclaim the division from their northern rivals. And early on in 2025, it looked like that plan might just work.
By the time June rolled around, the Cubs were flying high, holding a 5.5-game lead over Milwaukee. The offense was clicking, the rotation was holding steady, and Wrigleyville had the feel of a summer revival. But baseball seasons are marathons, not sprints-and the Brewers knew how to pace themselves.
Milwaukee caught fire as the summer heated up. That early cushion the Cubs built?
It evaporated fast. By the end of June, the Brewers had trimmed the deficit to just 2.5 games.
And when August arrived, they were back in familiar territory-first place in the NL Central. From there, they never looked back.
Not only did the Brewers win the division again, but they also delivered a statement in October, knocking the Cubs out of the postseason in the NLDS to cap off another dominant year.
That loss left the Cubs with more questions than answers. And now, as the offseason gets underway, Chicago’s front office-led by president of baseball operations Jed Hoyer-is staring down a tough winter.
Kyle Tucker, the centerpiece of last offseason’s splash, is expected to head elsewhere in free agency. Replacing his production in the lineup is a tall task on its own, but the bigger challenge might be narrowing the gap between the Cubs and a Brewers team that’s now taken four of the last five division crowns.
Interestingly, despite Tucker’s looming departure, much of the Cubs’ early offseason focus has been on the mound. The front office has been aggressive in pursuing top-tier pitching, signaling a desire to reshape a staff that couldn’t quite keep pace with Milwaukee’s depth and consistency.
One of the biggest names connected to Chicago was Dylan Cease-a potential ace who could have transformed the rotation. Cease, a former Cubs prospect, was rumored to be on the team’s radar almost as soon as the offseason began.
But that pursuit came to an end just before Thanksgiving, when the Toronto Blue Jays swooped in with a seven-year, $210 million deal. It’s a major investment for the reigning AL champs, and it also sets a steep market for frontline starters across the league.
On the bullpen side, the Cubs had eyes on Ryan Helsley, the hard-throwing former Cardinals closer. And while Chicago doesn’t typically shell out big money for relievers, they made an exception earlier in the week by signing Phil Maton to a two-year, $14.5 million deal.
Helsley was next on their list-but again, they came up short. The Baltimore Orioles locked him up with a two-year, $28 million contract, reportedly outbidding Chicago in the process.
So now, the Cubs find themselves in a familiar offseason position: back at the drawing board. With Cease and Helsley off the table, the team will need to pivot toward secondary options-whether that means targeting mid-tier free agents, exploring the trade market, or taking calculated risks on bounce-back candidates.
The challenge? Supply and demand.
Plenty of teams are hunting for arms, and with the contracts Cease and Helsley just landed, the price of pitching isn’t coming down anytime soon. That’s the kind of market that can force front offices into uncomfortable decisions-overpaying for talent or rolling the dice on unproven depth.
For the Cubs, it’s a critical moment. They’ve shown they’re willing to spend, and they’re clearly committed to closing the gap with the Brewers.
But with their top targets now off the board, the next few weeks will test the creativity and conviction of Chicago’s front office. The NL Central isn’t waiting for anyone-and if the Cubs want to unseat the Brewers, they’ll need to find answers fast.