The Cubs’ Quest for October: A Season of High Stakes and Expectations
MESA, Ariz. — The Chicago Cubs are gearing up for what they hope will be a transformative season, one that sees them return to the playoffs for the first time in five years. It’s been three and a half years since the Cubs decided to overhaul their roster at the 2021 MLB trade deadline, and now, as they prepare for the 2025 season, the team believes that their efforts are about to pay off.
The Cubs have made it clear that this winter is different from recent ones, with a palpable sense of urgency driving their actions. From the front office’s strategic moves to the team’s mindset as they report to camp, the message is clear: October baseball is the goal.
“I think we’re in a competitive window,” said Jed Hoyer, the Cubs’ president of baseball operations, as the team reported this week. “I think we’ve gotten better each year. I think we’re at a place where we have a chance to be really good and we’ve been trying to really maximize our resources within our budget to make sure that we can do that.”
While the Cubs aren’t spending like the Los Angeles Dodgers or New York Mets, they also aren’t in the same category as the Pittsburgh Pirates or Milwaukee Brewers. Last season, the Cubs were one of nine teams with a payroll that exceeded the luxury tax limit, yet they missed the postseason. Ownership is eager to change that in 2025, although they were outbid by the Boston Red Sox for top free agent Alex Bregman.
Despite missing out on Bregman, the Cubs have added significant talent to their roster, including newly acquired outfielder Kyle Tucker. Tucker’s arrival this winter marked a shift in strategy, as the Cubs traded three players, including a recent first-round draft pick, for the soon-to-be free agent.
“You don’t make a trade for Kyle Tucker if you don’t feel like you have a really strong team going into that year,” said general manager Carter Hawkins. “And so certainly I would say objectively we’ve improved year over year in terms of just the talent level that’s on the field — and in the three-plus years I’ve been here, this is certainly the most talented team we’ve had.”
The projection systems seem to agree, with predictions ranging from 87 wins (ESPN BET) to 90 wins (PECOTA). According to ESPN’s Bradford Doolittle, the Cubs are projected to win a National League Central-best 84.9 games, giving them a 39.3% chance of winning the division. Whether they reach these lofty projections, the team is poised to make significant strides in Craig Counsell’s second year as manager after consecutive 83-win seasons.
“It should feel like this all the time,” Counsell told ESPN earlier this week. “From that perspective, it makes me happy that we have high expectations.”
Counsell acknowledged that the team had to “rebuild a few things” after trading former stars Anthony Rizzo, Kris Bryant, and Javier Baez in 2021. This rebuilding process consumed much of the five-year contract Hoyer signed after Theo Epstein stepped down in November 2020. With this season left on his deal and no extension in sight, Hoyer is acutely aware of the potential impact this year could have on his future.
“I’ve been here for 14 years and sort of generally in my career, I haven’t had much uncertainty,” he said last weekend. “And so I think with uncertainty does come a level of anxiety. I think that would be a lie to say that it doesn’t.”
This sentiment wasn’t lost on his handpicked manager. Hoyer made waves when he hired Counsell from division rival Milwaukee, making him the highest-paid manager in the game. Now, Hoyer’s fate is, at least in part, tied to Counsell’s ability to maximize the potential of the team the front office has assembled.
“That makes it fun in my opinion,” Counsell said. “It provides a lot of clarity. And I’ve said that to Jed. It’s like, ‘Let’s go.’ I think that’s how he sees it. It can give you a lot of clarity in how you do things. We’re excited to try and do it together. I hope he’s here for a long time.”
As the Cubs’ position players report to camp Friday, several factors could determine whether this season is a success or a disappointment.
The Stars Have to Play Like Stars
Despite the talent bubbling up at Triple-A and a new group of depth players on the major league roster, Counsell emphasized the importance of the team’s best players stepping up. With a team projected to win in the mid-80s, which is often the threshold for playoff entry, there is little room for underperformance.
“Everything matters when you’re trying to get extra wins,” Counsell said. “You get it from wherever you can. Every decision is trying to add to that. … We’re going to rely on our regulars. We need production from our regulars, offensively and defensively.”
Last season, high-priced shortstop Dansby Swanson struggled with a sports hernia injury that affected his performance. His ramp-up will be slower this spring, and second baseman Nico Hoerner, who had flexor tendon surgery, could miss a few days at the start of the season. Both players will be crucial, especially if rookie Matthew Shaw is the starting third baseman.
In the outfield, Ian Happ has consistently delivered reliable 115 to 120 OPS+ seasons, while dynamic center fielder Pete Crow-Armstrong is beginning to realize his potential. If Seiya Suzuki, now the designated hitter, can put together a solid six months, the Cubs’ offense could be explosive.
However, the key to the lineup will undoubtedly be Tucker. He has the ability to impact a game in a way no other Cub can, and it comes in his free agent season.
Before acquiring Tucker, Hoyer raised eyebrows by stating that his players needed to “exceed” expectations, leading fans to question why the team wasn’t acquiring players with higher ceilings. Now that the club has one, it needs the best version of him with others filling their roles. It’s a good offense that could be great if it clicks.
Who’s on Third?
Bregman wasn’t one of the Cubs’ primary targets entering the offseason, so perhaps they’re not overly disappointed or surprised he’s not on their team. But his potential fit at third base had fans salivating as the winter played out. Well, at least until Wednesday night, when Bregman signed a three-year, $120 million deal with the Red Sox.
Adding Bregman would have pushed those projection models over 90 wins and given the Cubs a clear path to the postseason. The road to October remains a little less clear with Shaw the likely Opening Day third baseman, but the Cubs believe he could open some eyes around the league.
Shaw is the No. 23-ranked prospect in all of baseball entering the season, according to ESPN’s Kiley McDaniel, but comes in a little undersized for the hot corner. At 5-foot-9, he has power that would certainly play at second base, but he’ll be relied on to provide pop playing at a corner.
Michael Busch, who hit 21 homers in 152 games last season, is also on the smaller side for his position at the other infield corner as a 6-foot-1 first baseman.
- “It’s not the biggest group on the corners,” one scout said. “But that doesn’t mean they can’t slug. Busch outperformed some expectations last year.”
Not having traditional sluggers at the corners also means the true power hitters on the team — Tucker, Swanson, Suzuki, and Happ — are going to be relied on even more.
The Bullpen Must Deliver
The Cubs blew six games that they led entering the ninth inning last season — third most in baseball. Six is also exactly the number of games Chicago finished behind the third NL wild-card team. In overhauling their bullpen for 2025, the urgency to lower that number came by adding experience.
The Cubs acquired five pitchers — Ryan Pressly, Eli Morgan, Ryan Brasier, Matthew Boyd, and Caleb Thielbar — who took the mound in the playoffs over the past two seasons, and four of them pitched last October.
“When I looked at the roster in spring training this year, compared to last year, I think that was the No. 1 thing,” pitching coach Tommy Hottovy said. “It’s not only the number of bodies but the amount of major league caliber pitchers that have been there and done that.”
Acquired from the Houston Astros late last month, Pressly is the biggest name and could fill a crucial role for a bullpen searching for a competent closer after cycling through one failure after another last season. There were plenty of ninth-inning options on the free agent market this winter, but budget constraints along with Chicago’s overall feelings on many of them outside of Tanner Scott (who chose the Dodgers over the Cubs last month) led to a trade for Pressly.
“I want to be somebody that all these guys can lean on,” Pressly said in his introductory news conference. “Any questions that they have, on or off the field, I want to be that guy for them.”
Counsell added: “When you pitch in those situations, your team is like 10 minutes away from a win. That’s what makes it feel like more for guys that pitch in that situation. We rightly assign some credit for guys with experience there.”
With a revamped lineup and bullpen entering a crucial season, the Cubs hope they are just a smooth ninth-inning away from enough wins to be one of the last teams standing in October.
Originally Written by: Jesse Rogers
