My Offseason Blueprint for the Cubs: Big Moves to Suit Big Ambitions

[Matthew Trueblood]

I've become a broken record on this: the Cubs are a big-market team with big-market dreams, and they should be held to a standard befitting that status. That means they should spend big money each offseason to make their club better, and as they head into an offseason chock-full of big decisions, it means they should be extremely aggressive—not just financially, but in their embrace of some risk and the restructuring of a roster that has not kept up with the Brewers for the last decade.

To sketch out such a busy winter, I turned to our Offseason Blueprint tool, wherein you can build your ideal Cubs roster for 2027 one piece at a time. Check it out and build your own blueprint, but in the meantime, here's mine.

A Trio of Reunions: Re-Signing Players on Whom the Cubs Can't Improve

One of the harsh realities of this particular offseason is that the free-agent class is not rich with great choices, particularly on the position-player side. I therefore started my blueprint by forecasting re-ups between the Cubs and three role players who were important to the 2026 team, to set a solid floor for their roster-building. I slotted in Carson Kelly, whom the tool prices at $11 million per year. (I think that's a little high, but it's close enough.) This is not, in my opinion, an especially likely reunion. Nor is it an ideal solution at catcher.

I've written about this already. I think the Cubs should be looking for the next version of Kelly, on whom they got a great deal two winters ago, rather than either re-signing Kelly or turning the position over to overhyped prospect Owen Ayers. An updated version of Kelly from two years ago really isn't out there, though, and the Cubs seem to believe much more than I do in Ayers, so I expect them to sign a lower-level backstop and go into the season with Miguel Amaya and Ayers as Plan A behind the plate. On balance, I think they'd be better off sticking with Kelly for a bit longer, at least as a failsafe. It would be relatively easy, should Ayers work out the way the team believes he will, to jettison Amaya, so there's little risk of a real (or certainly a problematic) surplus.

I also advocate for the team bringing back two players they acquired from the Mets this summer: outfielder Tyrone Taylor and left-handed pitcher David Peterson. Taylor is a great fit for a roster that features a lefty-batting primary center fielder, in Pete Crow-Armstrong. He can also fill in admirably in the corners; he's just good enough to trust as an injury fill-in regular. For reasons that will become clear later, filling an outfield slot with a trustworthy right-handed bat was important. Peterson, meanwhile, made tangible improvements after joining the Cubs and should have drawn a playoff start. He should fit solidly into the fourth spot in the team's rotation, if things go well.

The First Big Splash: A Big Bid on a Posted Slugger

It's unlikely that Teruaki Sato will break the bank. He seems positioned for a deal similar to the one signed by Seiya Suzuki five winters ago, when the Cubs nabbed Suzuki on a five-year deal worth $85 million. (They also paid Suzuki's NPB team, the Hiroshima Carp, over $14 million as a posting fee, so their total investment in Suzuki was approximately $100 million.) Sato ranks ninth on our DiamondCentric free agent list. MLB Trade Rumors projects that he'll sign for $80 million over five years; FanGraphs projects $100 million over the same term. 

Suzuki was a slightly safer candidate to bring his productive bat to the American majors. He turned 28 in August of his first year Stateside; Sato will turn 28 next March. Suzuki put up a better OPS and (crucially) better strikeout and walk figures in his final seasons in Japan than Sato did. Sato has been compared more often to Munetaka Murakami, the biggest name among Japanese hitters who came over last winter, whose swing-and-miss issues limited his market. For many outsiders, what's buoying Sato's market is merely the fact that Murakami outperformed the modest two-year deal he signed with the White Sox last offseason.

I know our Jason Ross is not a big believer in Sato, but I am. Though he's more aggressive than Murakami (or Suzuki), Sato has much better feel for contact than Murakami did in his final years in Japan. Watching him, I see a more flexible swing and a quieter operation, and that was reflected in his in-zone contact rates in NPB. Sato also handles breaking stuff well. He might have to make some difficult adjustments to handle the velocity common in MLB, but I believe he'll hit almost as well as Suzuki did over his first five big-league seasons. Sato is a lefty batter, like Murakami, and like Murakami, he played third base more than any other position during his time in NPB. Evaluators expect him to play more first base in the States, but I think the Cubs should make a big bid and reel him in to become their starting right fielder. If he doesn't work out there but his bat is solid, he might also be able to take over for Michael Busch, should the latter continue to underperform at first.

(A quick note on Busch, while we're here, because I keep hearing whispers along these lines: No, he can't play anywhere but first base. He's not a good enough athlete or a skilled enough defender to play even a corner outfield spot. It's a flat, firm no. He's a first baseman, and if his bat isn't good enough to be a plus first baseman, he simply won't be an above-average player. Accept that. Acknowledge it. Your hope for him has to stay tightly focused on the recovery of his power in 2027 and beyond.)

The Much-Needed Shakeup: Trades for Joe Ryan and Yandy Díaz

This is not a pleasant thought, but the fact is that the Cubs' window is not wide-open. They're not starting a competitive cycle; they're nearing the end of one. It's time, therefore, for a big move whereby the team cashes in some long-term, low-intensity value for players who can help them make the most of the 2027 season. I suggest two separate deals in which the team recoups some of the talent it's losing via free agency this year, while moving players whose value will always be higher for other teams than for Chicago.

That means trading Pedro Ramírez and Kevin Alcántara to the Twins for starting pitcher Joe Ryan. With a cadre of star infielders locked up on long-term deals, moving Ramírez on the heels of his strong rookie campaign could allow Chicago to pick up a two-time All-Star hurler with frontline starting upside. Ryan has a 3.79 career ERA and a 27.3% career strikeout rate. He's been much, much better before the All-Star break than after it, throughout his career, so the team needs to deal for him with a plan in mind. He should be lightly used early in the season, so he can be healthy and fresh come September and October. Do that, though, and Ryan is a perfectly strong playoff-caliber starter. Should he fail again down the stretch, the Cubs would (hopefully) be able to turn to the likes of Cade Horton and/or Ben Brown, whose injury issues make them impossible to count on for the first half but who could be brought along slowly to prepare them for high-value appearances next fall.

It also means trading Matt Shaw (and, inevitably, something else) for Yandy Díaz of the Rays. Díaz is getting old. He's under contract for just one more year (like Ryan), and he'll cost $13 million. On the other hand, he's an on-base ace and a righty bat with above-average raw power. He would bring balance and reliability to the top half of the Cubs lineup. Tying up the designated hitter spot is suboptimal, perhaps, but too many teams let that stop them from fielding a hitter as solid as Díaz. Shaw is still under team control for five more seasons, but he's never going to be an above-average corner outfielder, and the Cubs are committed to Nico Hoerner and Alex Bregman at the only other positions Shaw might plausibly play. They should swap him for Díaz and accept the fact that they're all-in.

The Big-Money Ace

So far, we've reinforced the rotation and the lineup, but you've been waiting for the big name and the big dollars. Where can the team realistically try to turn the corner from Wild Card contenders to serious October threats? You've waited long enough. Let's talk about Michael King.

The Cubs have been interested in King for a long time. I propose that they be the ones to land him this time, adding roughly $30 million in annual average value to their payroll on a three- or four-year deal. King opted out of his contract with the Padres this fall, after shutting down the Cubs in impressive fashion in late September and ending their season. He's not the household name or the reliable workhorse that Tarik Skubal is, but that's why he'll cost far, far less than Skubal will. Ideally, perhaps, the Cubs would be in on Skubal. Ideally, they'd also have much better depth already, so that Skubal could be the capstone on a championship-caliber roster. That's not where they stand as the offseason gets underway, Therefore, they need to turn their attention to King, instead. They can land him without being left hamstrung as they pursue other improvements.

3 More Important Insurance Policies

In theory, you could almost call the above a complete offseason plan. Make the moves enumerated here, and the 2027 Cubs would go:

Lineup

1. Yandy Díaz - DH
2. Pete Crow-Armstrong - CF
3. Alex Bregman - 3B
4. Teruaki Sato - RF
5. Michael Busch - 1B
6. Nico Hoerner - 2B
7. Carson Kelly - C
8. Tyrone Taylor - LF
9. Dansby Swanson - SS

Bench

• Miguel Amaya
• Gabriel Arias
• James Triantos

Starting Rotation

1. Michael King
2. Joe Ryan
3. David Peterson
4. Justin Steele
5. Edward Cabrera

Bullpen

• Ryan Zeferjahn
• Daniel Palencia
• Ryan Rolison
• Jacob Webb
• Shelby Miller
• Eric Orze
• Phil Maton
• Riley Martin

That's respectable. Whether it's better than 2026 is debatable, but this team is losing not only a slew of starting pitchers (Matthew Boyd, Shota Imanaga, Clay Holmes and Kevin Gausman, plus the fact that Horton and Brown now exist under a cloud of injury worry) but Suzuki and Ian Happ, which meant it was always going to be hard to get back even to last year's level. 

However, I see three major weak points that still need to be addressed. First, the outfield isn't robust enough. There's not even really a backup listed here, with Shaw and Alcántara shipped out of town and Taylor forced into the starting lineup. The Cubs need someone akin to 2026 Michael Conforto, pushing Taylor to the bench a majority of the time, but it shouldn't be Conforto himself; doubling down on veteran finds like that is a bad idea.

The starting rotation also isn't deep enough. Steele and Cabrera are better as names than as actual pitchers right now. Behind them lurk Brown and Javier Assad, plus (around July, you hope) Horton, as well as some other underwhelming options, but the Cubs need more depth. More depth means people can step in when injuries happen. It also means they can stretch the rotation to six hurlers more often, which is important for keeping the guys who are healthy fresh and available come the end of the year. 

Finally, the bullpen needs another sturdy arm. Counting on anything from Maton (whatever his remaining upside if he comes back healthy after knee surgery) feels foolish. Therefore, I have the team making three more free-agent moves.

Jake Fraley is no great shakes. If he's your starting outfielder, you're always looking for the chance to upgrade that spot. However, as a platoon partner for Taylor, the Cubs could do much worse. Fraley missed much of 2026 due to sports hernia surgery, which should keep his market very tame. He's a step better than Conforto was perceived to be last winter; the team would have to guarantee him a roster spot and a seven-figure salary. They should do it. He's the right kind of gamble, as a complement to bigger moves like signing Sato and trading for Díaz.

Kris Bubic would increase the team's susceptibility to an injury crisis in the rotation. So be it. He's also one of the highest-upside non-premium arms on this year's free-agent market. The southpaw would be a perfect final ingredient along with Ryan, King and the return of Peterson. The team would have so much starting depth that they'd end up struggling to juggle it, if everyone got and stayed healthy for a prolonged period, but if the Cubs don't plan to do that difficult balancing act, they'll end up doing a tougher, worse one: scrambling to find help when they suddenly don't have enough arms to field a rotation.

Finally, the team should scoop up semi-disgraced slider monster Kevin Ginkel. The surface-level numbers turned sour in Ginkel's walk year with Arizona, but his slider still misses bats at an exceptional rate. Add him to a mix that features Zeferjahn, Palencia and Rolison, and you have a sturdy back end of the bullpen, after all.

This would be a phenomenally expensive team. The Cubs would be over the second luxury-tax threshold, unless some major changes come to the collective bargaining agreement. They would also be stuck hoping for a lot of success in a short period; their outlook beyond 2027 would be somewhat dimmed. But if the team wants to go from where they are to where they want to be, they have to accept those tradeoffs. It's time to go for it, if only because they have no real alternative—and because the way things are now should be unsatisfactory to almost all Cubs fans.

Image courtesy of William Liang-Imagn Images

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[Jason Ross]

You know. I don't hate it, Matt. There are individuals on here I don't love (Sato, and really, King I have real reservations on), but as a full, cohesive unit that's a pretty solid team, especially if Sato is much better than I expect. 

[mul21]

I don't like this at all.  Sato strikes out too much, Ryan's shoulder is held together with duct tape and chicken wire, and counting on Steele to be the #4 is tenuous at best.  It also feels like you're giving away too much young talent for too few years of control coming back and you'll have to address all these issues again after the 2027 season without the resources that got traded away.

[SC Hoosier]

Feels to me like a case of overestimating value of your own prospects. Return for Ryan feels a little light, and Matt Shaw won't get you Yandy Díaz, not even close. 

[mk49]

I don't want Joe Ryan.  His 2nd half HR/9 is normally higher than Shota and Gausman.  He didn't even pitch at Wrigley.😁  He's a flyball pitcher who gives up a lot of HR's with very high ERA and FIP in the 2nd half, almost every season.  I don't expect him to pitch well in the postseason.  Besides, he'll be a rental.

I also don't like bringing Kelly back for $10+M AAV.  It's much better than trading for Ryan, though.

Edited 1 hour ago by mk49

[Rcal10]

38 minutes ago, SC Hoosier said:

Feels to me like a case of overestimating value of your own prospects. Return for Ryan feels a little light, and Matt Shaw won't get you Yandy Díaz, not even close. 

You know Ryan and Diaz are both in the last year of their deals, right? So they will be free agents after this year. If anything, too much is being given for those guys. 

[Matthew Trueblood]

44 minutes ago, Rcal10 said:

You know Ryan and Diaz are both in the last year of their deals, right? So they will be free agents after this year. If anything, too much is being given for those guys. 

(And those two evaluations, taken together, are why the value proposition is about right on each. 😄 ) 

[Tangled Up in Plaid]