Either the Cubs Payroll Increases or We Will be Dissapointed (And Other Cubs Bullets) ...Middle East

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Either the Cubs Payroll Increases or We Will be Dissapointed (And Other Cubs Bullets)

This Cubs offseason has stunk — no doubt about it — but the Bears are sustaining me. It’s been half a decade since our football team sniffed the playoffs … and a lot longer since we actually thought they had a shot at doing anything with their opportunity. So as I sit here today, bummed and annoyed by the all too familiar lack of aggression from the Cubs front office, I am perked back up by Caleb Williams chasing franchise history at Soldier Field this afternoon and continuing that momentum in the postseason.

Bear down, gang. And then keep this run going.

    When I was thinking about the rest of the Cubs’ offseason recently, I was struck by a harsh reality regarding their payroll. So far, the Cubs have spent ~$29.5M in CBT payroll upgrading their bullpen this offseason (plus another $1.25M for Tyler Austin), right? Generally speaking/in isolation, I think we’re mostly happy with those moves.

    The Chicago #Cubs have spent $29.5M upgrading and supplementing their bullpen this offseason (in terms of CBT payroll added). Phil Maton: $7.25M Hunter Harvey: $6MCaleb Thielbar: $4.5MHoby Milner: $3.75MJacob Webb: $1.5MColin Rea: $6.5M**Rea had an option

    — Michael Cerami (@Michael_Cerami) December 31, 2025 However, that atypical (for them) expenditure on the pen has dragged their luxury tax payroll all the way up to $209.6M. And while that leaves plenty of space beneath the first tier of the luxury tax ($244M), we have no reason to believe the Cubs are willing to get anywhere close to that. In fact, in the last two offseasons, the Cubs’ pre-season payroll limit seemed to top out around $215-220M. Yes, two years ago, it expanded when Tom Ricketts authorized an extra-budgetary layout for Cody Bellinger. And last year, it almost did when the same happened for Alex Bregman. But the implication was clear: $220M was their apparent payroll limit for before the season, and anything beyond that was available only under special circumstances (or later at the trade deadline if necessary). So … what does that say about what else they can do this winter? On the one hand, I have an EXTREMELY hard time believing Jed Hoyer would spend nearly $30M upgrading his bullpen while leaving no money for his rotation, especially with so many rotation needs popping up after 2026. Likewise, the Cubs hosted five playoff games at Wrigley Field and project well for next season, so maybe their default payroll moves up a tad? On the other hand, when has the logic of what the Cubs SHOULD BE spending ever met at the crossroads of reality? So, we’re basically left with this: Either the Cubs payroll is going to increase significantly this winter OR we’re going to be extremely *EXTREMELY* disappointed by what they’re able, willing, and ultimately going to do the rest of the way. So what’s it gonna be … Is the beer bat half empty or half full? (Yes, it’s possible there’s some unforeseen trade that could help them thread the needle, but I never count on trades happening.) While the BN Cubs Podcast took the holidays off, North Side Territory is back and discusses the Cubs’ potential next moves with a heavy focus on Zac Gallen. They also discuss the Cubs’ penchant for waiting to see which free agents are lingering on the market into Spring Training (a la Bellinger and Bregman) and wonder if that same thing will happen for them again this offseason. Shrug. It’s a fine approach if those last additions are purely incremental to an already great team, but I don’t think we’re there yet. So…why don’t you just go out and make us better already. Thanks. In case you missed it yesterday, Kazuma Okamoto signed a right-on-target four-year, $60 million deal with the Blue Jays on Saturday, which definitely opens up a lot of questions for Kyle Tucker, Bo Bichette, and Alex Bregman, among others.

    Kazuma Okamoto Signs with the Blue Jays t.co/d8WD7O4KRW

    — Bleacher Nation (@BleacherNation) January 3, 2026 Remember Carlos Silva? Dude was pretty legit in his 21 starts for the Cubs in 2010: 4.22 ERA, 3.75 FIP with a 48% groundball rate and 13 quality starts (plus a handful more that were close).

    MORE CUBS FROM BLEACHER NATION: Go Ad Free | Subscribe to the BN Newsletter | Listen to the BN Cubs Podcast

    Somehow, the Bears are going to be playoff underdogs *at home* no matter who they play in the first round. I kinda love that. Bears Will Be Playoff Underdogs No Matter What, Injury Notes, Caleb Williams Fun Facts, and Other Saturday Bullets

    This hoodie remains the coolest thing @obvious_shirts has ever made for the Bears. Get one here: t.co/PdrMm1K3JZ pic.twitter.com/sc0P8mB64o

    — Michael Cerami (@Michael_Cerami) January 4, 2026

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