Chicago Cubs: 4 offseason steps to a 2027 World Series

Okay, the title of this column is a bit clickbait-y. The Chicago Cubs have a lot to do this offseason if they want to even make a serious playoff run.

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A cause for optimism, though, is that while a lot needs to be done, their needs are very well-defined and simple to target. They need pitching—especially starters and back-of-bullpen arms—and they need to handle the catcher and corner outfield spots, which could soon be vacant due to free agency.

They’ll also have the funds to make a number of big moves as lots of money is coming off the books this offseason.

So a path to a 2027 World Series—in what may be an abbreviated season, anyway, due to the looming labor dispute—is there and, actually, not all that far-fetched. Here are four steps the Cubs must take to get there:

Become free agent pitching buyers

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With their entire end-of-season starting rotation possibly leaving via free agency and nothing but question marks left behind, the Cubs can’t afford to go bargain hunting for pitching as they usually do. They need to spend and there’s no way around it.

It would be beyond nice to have Tarik Skubal at the top of the rotation, but the reality is that Chicago needs bulk when it comes to starting pitching. Grabbing at Skubal would probably mean ending the shopping spree right then and there.

Instead, the Cubs need to go semi-deep on two free agent rotation buys and then maybe on a solid fifth starter as well. They could explore a second chance for Clay Holmes or possibly Michael King or Freddy Peralta—among many options this offseason—and then go about trying to bring David Peterson back as well.

Chicago also needs to make a big play for reliever Adrian Morejon, who would be a perfect fit for the back-end of a bullpen that is actually not that far from being where it needs to be.

Three free agent starters and Morejon would be wonderful, but two starters and Morejon might be sufficient given the next suggested offseason step.

Trade for a controllable arm

The Cubs’ move to do this with Edward Cabrera last offseason didn’t work out at all, but that doesn’t mean they should stop trying. A deal to bring in someone like Reid Detmers from the Los Angeles Angels should be prioritized, even if it involves making some uncomfortable trade decisions.

Bring back Carson Kelly

With so much new pitching coming in, the Cubs will need a steady, experienced catcher behind the plate. This wouldn’t be the time for a Miguel Amaya/Owen Ayers backstop takeover.

Kelly has become a team leader as well as a solid contributor on offense. The Cubs will eventually want Ayers to be their every day guy, but 2027 wouldn’t be the right time for that.

One more year of Ian Happ

In a perfect world, the Cubs could find some way to extend Seiya Suzuki before he hits the open market. But the right fielder will almost surely dive into the deep end of the free agent talent pool, where he’ll be a big fish. Given the Cubs’ other pressing needs, they won’t get into a bidding war for his services.

With Suzuki leaving, Chicago would be wise to see if Happ accepts the $23.1 million qualifying offer for at least one more season in Wrigley.

Happ definitely has his defects, but he’s better than anyone else the Cubs have on the team as a Plan B for left field. Chicago could do a lot worse than a Gold Glove defender with 20+ home run potential. One more year of Happ would also allow the team’s outfield prospect studs (Josiah Hatshorn, Kane Kepley, and Ethan Conrad) to take one or two steps closer to the majors.

The coming season should be an interesting one for the Cubs and their fans. The core of an outstanding team is there, they just need to make some aggressive and savvy moves this offseason.

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Source: https://www.chicitysports.com/chicago-cubs-4-offseason-steps-2027-world-series-happ-suzuki-kelly-detmers/