Chicago Cubs’ options for rebuilding a broken starting rotation

The Chicago Cubs are in a self-created limbo right now.

They are close enough to contention—7.5 games behind the NL Central Division-topping Milwaukee Brewers and one game away from a Wild Card spot—to still consider big moves by this season’s August 3 trade deadline. However, losing twenty-two of their last thirty games kind of tells the tale that this team just may not be built for postseason glory this year.

More News: Chicago Cubs: Consistent Ian Happ making his case for an extension amid 2026 disaster

Do they go “all in” for a desperately-needed starting pitching pickup, trading away some precious prospect capital for a longshot chance of doing big things in the playoffs? Or do they hold back and cross their fingers for a team surge “as is” while keeping their eye on making a real run next season?

The wise choice, given the realities of the team we’re seeing, is to work towards the latter. Although a best of both worlds option may be to take a stab at both by acquiring a pitcher with years of team control at the deadline.

Realistically, though, the Cubs are facing the choice of trading for rentals or not.

So, then, what options will there be for a 2027 soft rebuild?

Headed towards a soft rebuild in 2027?

More News: Chicago Cubs: That uncomfortable Craig Counsell conversation is coming soon

In terms of position players, we know that five of eight slots are already filled: Michael Busch at first, Nico Hoerner at second, Dansby Swanson at shortstop, Alex Bregman at third, and Pete Crow-Armstrong at center field.

The fates of corner outfielders Ian Happ and Seiya Suzuki, along with catcher Carson Kelly—who are all free agency-eligible at the end of the 2026 season—will very much be up in the air.

The bullpen will also be up in the air, except for Daniel Palencia, Phil Maton, and maybe one or two others pieces. But the Cubs have routinely succeeded with pieced-together bullpens on the fly.

The real concern will be starting pitching.

Cubs need to spend on starting pitching

As of right now, the only Cubs starting pitchers guaranteed to be on the team next year—and healthy enough to start the season—are Edward Cabrera, Ben Brown, and Javier Assad.

Cade Horton is expected back from elbow surgery sometime around mid-season. Meanwhile, Justin Steele’s return date is still up in the air as he’s experienced a setback in his own recovery from elbow surgery.

In terms of outgoing free agents, Jameson Taillon is a goner, for sure, and Shota Imanaga will most likely be gone as well. Matthew Boyd’s injury-plagued year may actually work in favor of him and the team coming together on their mutual $15 million option for 2027, although the Cubs may be wise to move on if they’re depending on him as anything other than a fourth or fifth starter at that point. The Cubs have a $7.5 million team option for next season on sturdy, steady swingman Colin Rea and would be crazy not to exercise it.

All of this means that the Cubs will head into the 2027 season with at least three rotations spots to fill and $40 million in Taillon and Imanaga savings to spend ($55 million if they don’t hold on to Boyd). Plus, add another $20 million+ from losing either Happ or Suzuki to free agency.

That should be enough to pick up at least two studs for the front of the starting rotation.

One can probably rule out Tarik Skubal right off the bat. The Cubs are just not the type of team that will ever spend THAT kind of money on anyone, especially a pitcher.

But there are other options. Freddy Peralta, Robbie Ray, Zac Gallen, and Brandon Woodruff will for sure be out there, barring some unforeseen extension. Corbin Burnes, Michael King, and Sonny Gray will also probably opt to test the free agent market. The 2027 pitching market will actually be pretty deep. And given the Cubs’ conservative nature when it comes to paying for pitching, it wouldn’t be unreasonable to see Imanaga return to the club at a significantly discounted price.

There WILL be options for the Cubs to build a true playoff-caliber starting rotation for 2027 and beyond. The question is whether Cubs president Jed Hoyer and the front office will finally invest in doing that.

The post Chicago Cubs’ options for rebuilding a broken starting rotation appeared first on ChiCitySports.

Source: https://www.chicitysports.com/chicago-cubs-starting-rotation-needs-free-agency-2027/