Touching Base: Cubs Have a Revamped Look and Even Bigger Expectations

Expectations are rising on the North Side of Chicago. After breaking a four-year playoff drought, the Cubs know that simply getting a spot in the dance won’t be enough in 2026. 

Not after the breakouts of Pete Crow-Armstrong and Cade Horton. Not after the additions of Alex Bregman and Edward Cabrera. And not after losing in the National League Division Series to a Brewers team that won the NL Central for a third straight year. 

"Everyone had high expectations last year, and I think they’re higher this year," Cubs owner Tom Ricketts acknowledged to reporters last month. "Obviously, we want to win the division. We should win the division." 

His players stand by that assessment. 

"I fully expect us to win the division," new Cubs reliever Hoby Milner echoed this spring. "I would assume everyone else expects us to win the division."

Alex Bregman and Edward Cabrera are two of the biggest additions at Wrigley (Getty)

They do, at least according to most projection systems. 

If the Brewers are going to shock the world again by winning a fourth straight division title, it will require defying the models. 

Baseball Prospectus’ PECOTA standings project the Cubs for 90.5 wins and the Brewers for 82.2. BetMGM set the over/under for Cubs wins at 88.5 and the Brewers at 84.5. FanGraphs gives the Cubs a 43.1% chance to win the NL Central this year.

There’s a reason for all of that, beyond the typical Milwaukee neglect. 

The Brewers traded away from their big-league roster, dealing ace Freddy Peralta to the Mets and 2025 standout Caleb Durbin to the Red Sox. The Cubs, meanwhile, continued building this winter in search of their first division title since the shortened 2020 season. 

They needed another difference-maker in the lineup after Kyle Tucker hit free agency, and they added Bregman. They sought another impact arm, and they traded for Cabrera. They watched most of their relievers depart and replaced them with new ones, including a trio of arms in Phil Maton, Jacob Webb and Milner who helped lift a Rangers bullpen that defied expectations in 2025 by producing the fifth-best ERA among all relief units. 

"It’s the biggest market that I’ll have had an opportunity to play in," said Milner, who played for the Brewers from 2021-24. "I’m looking forward to being on the road and having Cubs fans matching the home fans, that kind of thing. I’ve always been on the opposite end of that. Going to play in Milwaukee and it being a home game, for the most part, that sounds pretty appealing to me. But also being expected to win the division, that’s where I want to be."

 Pete Crow-Armstrong has a new deal in the North Side. (Chris Sweda/Chicago Tribune/Tribune News Service via Getty Images)

If it’s all going to finally come together for this Cubs core, it may need to happen now.

Nico Hoerner, Ian Happ, Seiya Suzuki, Shota Imanaga and Jameson Taillon are among the Cubs mainstays entering their final season under contract in Chicago. In addition, 2025 All-Star Matthew Boyd, catcher Carson Kelly and pitchers Hunter Harvey and Caleb Thielbar have mutual options in 2027, which rarely get exercised. Dansby Swanson, Bregman and Crow-Armstrong, who just signed a six-year extension through 2032, are the only players signed beyond 2027. 

"When the group knows each other and knows each other’s expectations — we know we’re going to play great defense, we know the expectation is to be the best baserunning team in baseball — and when you have that standard, it makes it a lot easier to just go out there and focus on winning," said Happ, who was drafted in 2015 and a top prospect when the Cubs last won the World Series in 2016. "I think the expectations as a whole for the team are a deep playoff run, but that starts with your process every day." 

Matt Boyd was a 2025 All-Star. (Photo by Matt Dirksen/Chicago Cubs/Getty Images)

Helping with that daily process is a new leader in the clubhouse. When the team reported to camp in February, many of the veteran Cubs players noted a different energy. The presence of a two-time world champion played a part. 

Within days of Bregman leaving Boston for Chicago in a move that shocked many around the sport, the three-time All-Star had already reached out to the Cubs’ front office for reports on all of his new teammates. 

"I feel like you want to know what people are working on because you don’t want to talk about conflicting messages," Bregman told me last month. "You want to all be pulling on the same end of the rope, get to understand guys and learn what they’re working on. It’s just something I’ve always liked doing and something I’ve always seen my teammates do."

Seiya Suzuki is one of several Cubs players who are entering the last season of their deal. (Photo by Matt Dirksen/Chicago Cubs/Getty Images)

In past stops, Bregman was renowned and respected for his ability to positively impact teammates. His new ones in Chicago are quickly understanding why. 

"He loves talking baseball, loves being around the field and loves talking about doing little things to help the group win," Happ said.

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The same way Boyd felt he got better as a young pitcher simply by being around Justin Verlander in Detroit, he sees a similar gravitational pull with Bregman, who changed his number from 2 to 3 as he seeks a third championship title. 

"It’s not some magic equation or mythical thing," Boyd told me. "It’s someone that shows up every day ready to win and trying to find wins in every single margin…Rising tide raises all ships. It raises the water level."

As Bregman works to create new relationships and offer bits of advice, he’s just trying to play his part for a team that’s finally returning to relevance after a decade of disappointment. In the nine seasons since the Cubs won the 2016 World Series, they’ve only won the division twice. The last time was in 2020.

Since then, it’s been a slow rise back to prominence: 71 wins in 2021, 74 in 2022, 83 in 2023 and 2024 and 92 in 2025. They ended the four-year playoff drought last season, but another jump forward would likely mean finally knocking the Brewers off the NL Central pedestal. 

The Cubs believe that’s about to happen. 

"We’re a better version of what we were last year, and we’re hungry in that sense," Boyd said. "We know where we’ve got to go." 

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