2025 is the final year of Chicago Cubs President Jed Hoyer’s contract. In those five years, the Cubs have played exactly ZERO playoff games. Hoyer knows this year is likely his last chance to reach the post-season on the north side. Hoyer knows what ownership and fans expect.

“Does it feel different than it has in the past,” Hoyer asked on day one of Spring training in Glendale, Arizona.” A little bit. I’ve been here for 14 years, and sort of generally, in my career, I haven’t had much uncertainty. 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.”

The Cubs need to answer at least three questions before the 2025 season begins. It starts early in Japan against the World Series Champion Los Angeles Dodgers on March 18.

1. Cubs Questions for 2025 — The Rotation

What do the Chicago Cubs need in 2025?

The Cubs’ first question is the starting rotation. What happens after Shota Imanaga’s out-of-this-world rookie season in Chicago?

Shota Imanaga

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15-32.911.021174173.1

Right now Justin Steele is the clear #2 starter. The Lucedale, Mississippi native needs to stay healthy after throwing just 135 innings in 2024. Steele was on the injured list twice in 2024. He suffered a hamstring injury on opening day, and had elbow tendinitis in late in the year.

Justin Steele

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5-53.071.1013537

After Steele it’s all hands on deck. Going into camp it’s Jameson Taillon, Matt Boyd, Colin Rae, Eli Morgan and Javier Assad. Assad is starting spring training on the shelf with a sore oblique.

Wild cards in the Cubs rotation could be San Diego Padres’ pitchers Dylan Cease and Michael King. Both are in the final year of their contracts. The Cubs have sat out of the chase for the big-name free-agent pitchers, but Cease and King could be available. The Padres are looking to save a little money.

2025 will be just King’s his second year as a full-time starter. He started 30 games with an ERA under three. Cease didn’t have a spectacular 2024, but he’s got a history of dominance. The six-foot, 200 lb right-hander was just 14-11 with a 3.47 ERA in San Diego in 2024.

2. Cubs Questions For 2025 — Alex Bregman

Will the Chicago Cubs pursue Alex Bregman?
Alex Bregman

The talk of Alex Bregman heading to the Chicago Cubs makes a lot of sense. The Cubbies had a long line of players at the hot corner in 2024, but none stood out. Bregman is one of the last two big free agents available. Nolan Aranado is still available but like all free-agents, he’s rumored to be headed to the Dodgers.

Bregman is just 30 years old and has played all nine years of his career in Houston. “I wouldn’t rule out anything,” said Jed Hoyer, the Cubs’ president of baseball operations. “You always look for opportunity, But right now, we’re going to have a meeting (Sunday) afternoon, we’re going to focus on the guys who are in camp and that’s the plan.

Chicago made one big move in the off-season trading for Kyle Tucker. They gave up power-hitting third baseman Isaac Paredes, right-handed pitcher Hayden Wesneski, and 2024 first-round Draft pick Cam Smith.

Tucker should hit second between Ian Happ and Seyia Suzuki to give the Cubs a powerful top three.

3. Cubs Questions For 2025 — The Bullpen

The Chicago Cubs have a new closer.

The Chicago Cubs bullpen was a disaster in 2024. It had 26 blown saves and 35 losses. The entire pen had just 42 saves. So it’s no surprise the team spent a lot of effort to improve it. Coming into 2025 one expert says the team now has a “bullpen of riches.” That will bring new challenges in choosing a roster.

Two trades brought in two new Ryans. Ryan Pressly came in from Houston to be the new closer. Ryan Brasier is now a Cub after a trade with the Los Angeles Dodgers.

The Dodgers worked their magic with Brasier after signing him from Boston in 2023. He had an ERA over seven in Boston. After getting to LA his ERA plummeted to 0.70 with a 0.724 WHIP in 39 games.

Ryan Pressly will back up the pen. He had 64 saves between 2022 and 2023. 2024 was challenging for Pressly after the Astros brought in Josh Hader. The relationship with the front office soured after Hader arrived. Chicago still needs a lefty in the pen and should be looking at options to bring someone in.