If you walked into the Sheraton Grand Chicago this weekend for the Cubs Convention, you probably felt it. That buzz isn't just the usual mid-January optimism that every fanbase manufactures to survive the winter. It’s different this time. After years of "intelligent spending" and "building from within," Jed Hoyer finally pushed his chips to the middle of the table.
The headlines are dominated by one name: Alex Bregman.
Seeing him in pinstripes with that No. 3 jersey—a number he chose because he’s hunting for a third World Series ring—changed the entire vibe of the 2026 offseason. But if you think the chicago cubs rumors and news cycle ends with a $175 million introductory press conference, you haven’t been paying attention to how Hoyer is moving lately.
The Bregman Ripple Effect: Who Stays and Who Goes?
Honestly, the Bregman signing is a massive win, but it creates a bit of a logjam that the front office has to untangle before Pitchers and Catchers report to Mesa. You can’t just drop an All-Star third baseman into a lineup and expect the rest of the puzzle pieces to stay still.
Matt Shaw is the name on everyone’s lips right now.
Last year, Shaw looked like the future at third. Now? He’s basically a man without a country. There’s a lot of chatter about Shaw potentially moving to the outfield or, more likely, over to second base. But wait. We already have a Gold Glover there named Nico Hoerner.
This is where the rumors get spicy.
The Yankees and Giants have reportedly been sniffing around Nico Hoerner. It sounds crazy to trade a guy who just won his second Gold Glove in three years and posted a 114 OPS+, but look at the math. The Cubs are creeping right up to that $244 million luxury tax threshold. Trading Hoerner would clear significant payroll and allow Shaw to slide into his natural middle-infield spot.
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Hoyer was asked about this directly during the Bregman presser. He did that classic front-office dance—sidestepping the question without actually saying "no." He mentioned that the team isn't done adding depth, which is GM-speak for "stay tuned."
The New-Look Rotation and the Edward Cabrera Gamble
While everyone was obsessed with Bregman, the trade for Edward Cabrera might actually be the move that determines if this team can catch the Brewers.
Giving up Owen Caissie hurt. Caissie was the No. 1 prospect for a lot of people, a power-hitting lefty who seemed destined for the Wrigley bleachers. But the Cubs needed a flamethrower. Cabrera brings a high-90s heater and a changeup that makes hitters look silly, even if his command occasionally goes for a wander.
The rotation is starting to look formidable, or at least very deep:
- Shota Imanaga: Back on that $22 million qualifying offer and still the emotional heartbeat of the staff.
- Justin Steele: He’s recovering from that late-2025 elbow surgery, but the latest news from the convention is that his rehab is ahead of schedule.
- Edward Cabrera: The high-upside wild card.
- Jameson Taillon: The steady veteran presence.
- Javier Assad / Colin Rea: The reliable back-end guys who probably don't get enough credit.
And don't sleep on Jaxon Wiggins. The kid is lighting up radar guns in the minors and there is a very real chance he forces his way onto the North Side by June. If Cabrera finds the strike zone and Wiggins is the real deal, this is a top-five rotation in the National League.
The Bullpen Makeover: No More "Cardiac Cubs"
If you watched the 2025 season, you probably have a few new gray hairs thanks to the bullpen. It was a disaster at times.
Hoyer clearly took that personally. He spent the early part of this winter "spamming" the market for veteran relievers. We’re talking about a complete overhaul.
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- Phil Maton: Two years, $14.5 million. He's the high-leverage stabilizer.
- Hunter Harvey: One year, $6 million. When he’s healthy, his stuff is electric.
- The Lefty Brigade: Hoby Milner and Caleb Thielbar.
- Jacob Webb: Another low-risk, high-reward arm for the middle innings.
The most shocking news, though, was Ryan Pressly announcing his retirement this weekend. There were some quiet hopes the Cubs might make a run at him to close games, but he’s hanging them up with 117 career saves. That leaves the closer role a bit up in the air. Does Porter Hodge get the first crack? Does Craig Counsell play the matchups? Knowing Counsell, he’ll probably use his relievers like a chess master, but having actual talent in the pen makes that job a whole lot easier.
Payroll Problems or "Champagne Problems"?
Let's talk about the money. The Ricketts family has a reputation for being, let's say, "frugal." But Bregman's $175 million deal (even with $70 million deferred) proves they’re willing to spend when the window is open.
The problem is the looming free agency of Ian Happ and Seiya Suzuki.
Both are coming off monster years. Happ just won his fourth straight Gold Glove. Suzuki drove in 103 runs. They are the heart of the outfield. But they’re both free agents after 2026. If the Cubs want to keep this core together while staying under the tax, someone has to be the odd man out.
There’s a growing sentiment among insiders that the Cubs might actually let the tax fly this year. If you're going to trade for Cabrera and sign Bregman, you don't half-heartedly compete. You go all in.
What Most People Get Wrong About the Farm System
A lot of folks think the Cubs "emptied the clip" by trading Caissie. Not even close.
Moisés Ballesteros is still here. The 22-year-old catcher/DH is a hitting machine. He’s likely going to start the year in Chicago, probably splitting time at DH with Suzuki and giving Miguel Amaya some breathers behind the plate. The kid has a professional approach that you just don't see in guys that young.
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Then there’s Kevin Alcántara. He had offseason core surgery, so his Opening Day status is a bit "wait and see," but his ceiling is still through the roof. The Cubs have built a "waves of talent" model where even if they trade a top prospect like Caissie, there’s someone like Ethan Conrad or Jefferson Rojas ready to climb the ladder.
What Really Happens Next?
The chicago cubs rumors and news aren't going to slow down as we approach February. The team is in a "win-now" posture that we haven't seen since 2017.
Keep an eye on the trade market for a backup catcher. Behind Amaya, it’s a bit thin. They signed Christian Bethancourt to a minor league deal, but that feels like a placeholder. If they can find a veteran backstop to mentor Ballesteros and stabilize the staff, that might be the final piece of the puzzle.
Also, watch the Nico Hoerner situation like a hawk. If he’s still on the roster by the time the team plane lands in Mesa, he’s likely staying. But if a team like the Mariners or Red Sox gets desperate for a middle-infield upgrade, Jed Hoyer is always down to talk.
Actionable Insights for Cubs Fans:
- Monitor the Waiver Wire: The Cubs have been aggressive lately (claiming Ben Cowles and Justin Dean). Expect more of these "marginal" moves to shore up the 40-man roster.
- Spring Training Battles: The most important one isn't at third base anymore—it's in the outfield. Watch how Craig Counsell rotates Matt Shaw, Pete Crow-Armstrong, and the veterans.
- The "Steele" Timeline: If Justin Steele isn't ready for April, the Cubs may pivot back to the free-agent market for a short-term veteran arm like Mike Clevinger or Michael Lorenzen.
- Convention Clues: Listen to the tone of the "Baseball Operations Update" this weekend. The front office usually drops subtle hints about their remaining budget and trade appetite during these fan Q&As.
The North Side hasn't felt this alive in January for a long time. The "Plan" is over. The "Window" is open. Now, they just have to go out and play the games.