To Win in 2027, Chicago Cubs Need to Join the 300 Club

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By the standards of their proudly second-tier billionaire owners, the Cubs spent lavishly in 2026. They not only splurged over the winter on Alex Bregman and a bevy of smaller signings, but took on over $15 million during the season in trades to bolster their roster. According to Cot's Contracts, their final estimated payroll for competitive-balance tax (CBT) purposes was $268 million, nearly $30 million more than they've ever spent before. In raw dollars, they spent just under $250 million, but that's still far more than they've spent before. Inflation in the market demands that a big-market team keep its payroll rising this way, but the Cubs haven't always done so; it's worth noting their commitment to this year's team.

Unfortunately, commitment in one season doesn't earn you extra credit the following year. The Cubs can't get cheaper in 2027 and hope to replicate their 89-win campaign this year. In fact, they can't even maintain this new franchise high in spending and hold out a reasonable hope in that vein. No, the magic number for next year's team is one that might turn Tom Ricketts's hair white: $300 million.

The team doesn't need to actually spend $300 million on the roster next year—which is a good thing, because there's absolutely no chance that Ricketts will do so. Again, this year, they spent around $248 million on the 40-man roster. The difference between that figure and the $268 million for CBT purposes is a flat rate paid by all teams to fund player pensions and benefits, plus the difference between what players actually received and the annual average value (AAV) of their contracts, after considering deferrals and other financial quirks. It's that CBT number that will have to exceed $300 million if the Cubs hope to contend next year—but that probably means driving actual spending past $265 million. Let's talk about why, and why the Rickettses should be willing to do it.

Firstly, four of the Cubs' most important players will be significantly more expensive next season. Pete Crow-Armstrong's six-year, $115-million contract kicks in in 2027. It only pays him $10 million—a bargain, for a player who will be the reigning NL MVP when he takes the field on Opening Day. That's already a big bump from this year, though. His base salary for 2026 was under $1 million. He got a $5-million signing bonus as part of his new deal, and he'll get such a huge windfall from the league's pre-arbitration bonus pool that he'll end up earning eight figures for on-field work this year, but the Cubs will have paid only a small fraction of that in salary. Next year, he not only actually costs $10 million, but will carry a CBT tax hit of just over $19 million.

Nico Hoerner's new deal begins, too, and bumps him from a real salary of $14.5 million (counting a signing bonus payment he received in June) to $25.5 million. His CBT hit rises from about $11.7 million to about $22.8 million.

Alex Bregman's CBT number is unchanged, but his deal deferred $10 million of his annual $35-million salary in 2026; it only defers $5 million in 2027. Finally, Michael Busch is arbitration-elgible for the first time this fall, and MLB Trade Rumors projects him for a whopping $5.4-million payday. On those four guys, alone, the Cubs are in line to owe about $25 million more than they paid in 2026, and their CBT number will rise by more like $33 million. Without making any upgrades or replacing anyone heading out the door, and without accounting for several smaller pay bumps, they're going to see that much of an increase in costs.

Let's pause a moment. You might be thinking that this exercise is a waste, because the collective bargaining agreement (CBA) expires on December 1, and the sport is expected to enter a prolonged offseason work stoppage. The owners are expected to push for a salary cap that could radically reshape the rule set of the sport and the financial balance between teams. Admittedly, the lockout is a virtual certainty, and a cap is at least a possibility. However, I'm on record with this already, and I'll renew my asseverations here:

There will be a 162-game MLB season in 2027.
There won't be a salary cap.
Not that much will change, really, except that significant time will be wasted as the sides bicker.

That could turn out to be wrong, but based on conversations with people within the game; others within broader labor circles; and some sources with key corporate partners of the league, I continue to think the risk of lost games and the likelihood of a meaningful change from the present system are both being overblown. There'll be a lockout; it'll be annoying. But it's unlikely to produce any change that truly shapes how rosters are built, and we should assume that the basic guidelines of the last half-decade will apply to the next one.

Ok, enough about that. Assuming a quasi-stasis in the rules, we can get back to figuring out how (and how much) the Cubs need to spend money this winter to get better. Bregman, Hoerner, Busch and Crow-Armstrong are probably not going anywhere, and they're probably going to be quite good in 2027, as a group. They'll be more expensive, though, which poses a problem, because the team has to replace three outgoing position players, too. Ian Happ and Seiya Suzuki got all the headlines down the stretch; their free agencies have loomed as storylines for over a year. Each made $19 million in 2026, and their CBT numbers were right in that range. That means the team should be able to comfortably spend $38 million to replace them, but (beyond those two players themselves, and Mariners star Randy Arozarena) the outfield market is frightfully thin this winter—and, of course, they don't really have $38 million to spend, unless they're willing to increase their payroll. Some of what went to Happ and Suzuki in 2026 is earmarked for the quartet we just talked about in 2027.

He got far less attention, but Carson Kelly is also an impending free agent—and that's a significant issue for the Cubs. The two-year deal Kelly signed with Chicago before the 2025 season only earned him $5.5 million per annum, even after he met both tiers of his playing-time bonus clauses in both campaigns. The contract includes a $7.5-million mutual option, but really, that's only worth $6 million, since Kelly gets a $1.5-million buyout when he turns down his side of it. That's precisely what he'll do, and when he does, he'll become the second- or third-best catcher on this winter's (again, thin) market. Even if the Cubs bring him back, they should expect to pay at least as much as they did the last two years, and they'd be paying it to a 32-year-old at a position where almost everyone ages poorly. Miguel Amaya, not much younger than Kelly but with much less service time, is only projected to earn $1.7 million via arbitration—but that's more than double what he made in 2026. To avoid getting worse behind the plate in 2027 (which they can ill afford to do), the Cubs will have to spend more money on that spot, too.

Then, there's the pitching staff. Shota Imanaga, Matthew Boyd, Kevin Gausman and David Peterson are all free agents-to-be, no questions asked or strings attached. The Cubs could tender Boyd a qualifying offer, and if anything, there's a stronger argument for doing so with him than there was for offering Imanaga the same tender last fall. Bring him back on a one-year deal worth roughly $23.1 million, though, and you've just raised Boyd's actual salary by over $6 million and his CBT number by $8.6 million, relative to 2026. Given his age, there's very little chance Boyd is better next year, so the Cubs would be paying that premium just to feel reasonably good about holding their ground.

Barring giving Boyd a QO, the team will watch a huge amount of pitching salary slough off in early November. Boyd made $17 million, with a $14.5-million CBT hit. Imanaga got $22.025 million on last year's QO. Gausman and Peterson essentially replaced Jameson Taillon; you can think about Taillon's $18 million as rolling off the books. Clay Holmes will turn down his player option, so a guy on whom the team spent about $4 million is also leaving. Hunter Harvey is unlikely to return. The Cubs will decline their side of a mutual option with Caleb Thielbar. They're freeing up something like $70 million in pitchers who won't be back.

This time, there's no immediate salary bubble rising to take away their spending room. Justin Steele and Edward Cabrera are expected to get only very small raises next year. Deadline acquisition Braxton Garrett will get less than $2 million via arbitration. Ryan Zeferjahn isn't even arbitration-eligible yet. Daniel Palencia and Ben Brown are, but their injuries and inconsistency mean neither is expected to crack $2 million in 2027 earnings, either. Ryan Rolison and Javier Assad remain affordable. Cade Horton is pre-arbitration. The problem is that, of all those guys, the only remotely trustworthy arms for next year are Palencia, Zeferjahn, Rolison and Assad, and even they come with question marks.

Cabrera, Steele, Horton and Brown carry major upside. They're capable of much better 2027 campaigns, mostly by simply getting and staying healthy. Then again, there are real reasons for deep concern about each, and there's almost no chance of any of them giving you (say) 160 strong innings. At the very least, you have to build a pitching staff with the idea that they're good for fewer than 400 good innings as a group. The challenge the Cubs face is building almost a whole playoff-caliber pitching staff, from scratch, because they had one of the worst staffs in baseball this year and are likely to see their best pitchers either leave or spend much of next year on the injured list.

It's hard to overstate how expensive the endeavor they face is. Though it's miles outside Jed Hoyer's comfort zone (let alone Ricketts's), they need to seriously consider signing Tarik Skubal to a megadeal—but that wouldn't solve their problems. What they really need is an offseason akin to the one they had under Theo Epstein and Hoyer in 2014-15, when they both signed Jon Lester and brought back Jason Hammel—only they need to go even further.

Skubal, Trevor Rogers, Sonny Gray, Michael King, Tyler Mahle and Freddy Peralta headline a reasonably deep corps of free-agent starters. David Bednar and Adrian Morejon are the headliners on the relief market. The Cubs really need to consider signing three of those players, even if they retain one of Boyd, Holmes or Peterson through some type of re-up. That would be phenomenally expensive, though. Unlike in the 2014-15 offseason (or in 2015-16, when they signed Jason Heyward but also bolstered their rotation with John Lackey), they don't have a terrific young, inexpensive core to facilitate that kind of maneuver. They'd simply have to crash through the doors and into the high-roller room where the Yankees, Dodgers, Phillies and Mets play.

Failing a massive winter spending spree (in a winter wherein that might be difficult), Chicago will have to get creative, in a way that seems beyond Hoyer's ability. They'd need to seriously consider trading Busch and signing a more reliable bat for first base, while scooping up some young pitching. They'd need to consider selling high on hype machine Josiah Hartshorn (a good idea, but probably a non-starter) to land a premium trade target. They'd need to make a whole lot out of a farm system that comes to not-very-much. No, the Cubs have to go spend $300 million (at least in CBT terms) to win in 2027. That feels unlikely, but if they don't do it, a deep run next October feels even more far-fetched.