Cubs Deadline Push For Ideal Starter Just Hit An Unexpected Snag

The Chicago Cubs face a complex negotiation as they eye Joe Ryan to bolster their pitching lineup amid trade deadline pressures.

Joe Ryan keeps looking like the kind of pitcher the Cubs should be chasing at the trade deadline, but there’s a catch that could make the whole thing messy.

The Minnesota Twins right-hander was already a name tied to Chicago last summer, and he’s back in the conversation again this year. ESPN ranked Ryan No. 4 on its list of trade candidates, and Jeff Passan and Kiley McDaniel put the odds of him being moved at 55%.

“Ryan was one of the lone survivors after the Twins' teardown last deadline -- and Minnesota was deep into discussions on deals involving him, as well. So, a move would surprise nobody, particularly considering that Ryan looks better than ever this season.”

That said, this is not the same setup the Twins had a year ago. Minnesota is still hanging around the American League Central race and remains in the Wild Card mix, which leaves real room for Ryan to stay put. So even with the buzz, he may not actually be available.

If he does hit the market, the Cubs would make sense as a suitor. Pitching is a need now, and Chicago’s bigger deadline goal is to add someone who remains under control beyond 2026. Ryan fits that description, since he’s controlled through the 2027 season.

But that’s where things get complicated.

The Cubs may not value that extra year the same way the Twins do, because baseball appears headed toward a work stoppage before the 2027 season. If that season isn’t wiped out entirely, a significant chunk of it could be lost. That means Chicago may not be buying “two months plus another full season” of Ryan in any practical sense.

And that reality could warp the market. Minnesota will likely sell the value of Ryan’s control as if all of 2027 counts. The Cubs, or any other interested team, will probably see it through the lens of the CBA situation instead.

That gap could make it hard to find common ground before the deadline. Ryan checks the box for what the Cubs need, but the thing standing in the way may not be talent or fit. It may be timing.

In Other News...

Justin Steele Update Just Changed The Cubs Pitching Picture

Justin Steele is moving closer to the next step in his recovery, with the Cubs left-hander expected to start throwing off a mound in August as he works back from an elbow injury. Steele has been sidelined since April 7, and while that timetable still leaves plenty of uncertainty, it at least gives Chicago a clearer sense of where one of its most important arms stands as the season grinds on.

For a Cubs pitching staff that has already had to absorb injuries and uneven results, any update on Steele matters. Manager Craig Counsell has already signaled that the rotation may not be the place to look for his return this season, which leaves the Cubs waiting to see how his rehab progresses and whether there is a path for him to help in some role later on. [Read more 🡒]

Cubs Draft Class Just Put Two Familiar Prospects On Notice

The Cubs 2026 draft class gave the organization a fresh injection of talent, starting with Ole Miss right-hander Cade Townsend in the first round and continuing with Texas A&M outfielder Caden Sorrell and first baseman Myles Bailey. On paper, it is the kind of haul that can change the look of a farm system quickly, especially when a team is trying to keep its pipeline stocked at multiple spots instead of leaning too heavily on one position group.

It also creates a ripple effect for players already in the system, because added depth can shift how the Cubs value their current prospects in trade discussions. Kevin Alcantara is the clearest name to watch with another outfield bat entering the mix, while Baileys arrival gives the organization another long-term first-base option to monitor as the summer market approaches. [Read more 🡒]