The Cubs are in a position that should feel comfortable and still somehow doesn’t. At 12 games over .500 at the All-Star break and sitting in firm control of the Wild Card race, Chicago has built a strong enough first half to justify buying at the deadline. But the gap between the Cubs and Milwaukee in the NL Central is still wide enough to keep the pressure on Jed Hoyer and the front office to do something meaningful before the deadline passes.
The good news for Chicago is that the lineup and defense have held up. The Cubs have the best defensive group in MLB, and they trail only the Dodgers in wRC+.
That kind of production gives the club some flexibility, even enough that they could consider moving a big-league bat this summer. But the real need is obvious: pitching.
ESPN’s Jeff Passan made that point plainly in a recent piece, and both of his Cubs fits are starters. That lines up with the reality of Chicago’s season, which has been hammered by injuries across the pitching staff. Cade Horton, Justin Steele, Ben Brown and Edward Cabrera have all been part of that long list of arms lost along the way.
Passan’s top name for the Cubs is Red Sox veteran Sonny Gray, whom he called the team’s “dream fit.” Gray has already been floated plenty as a possible target, and on paper it makes sense. But Passan also pointed out the reasons Chicago may not get far in that chase.
Gray has a no-trade clause, so any deal would need his approval. And even if he signs off, the money attached to his contract is a real obstacle. He is owed $10M in salary, plus another $10M tied to a buyout on a mutual option for the 2027 season.
That mutual option matters because those deals are rarely picked up, which leaves Gray as something of a $10M burden from the Cubs’ perspective. The cost in prospects might be manageable, but the bigger question is whether Hoyer will even get the green light to take on that kind of salary.
That’s where the second Passan fit becomes important. Tigers right-hander Casey Mize offers a different path, and a compelling one. He has posted a 2.79 ERA and 2.69 FIP over 14 starts this season for Detroit, making him a strong fallback if Gray proves too complicated or too expensive.
The Cubs may have the kind of roster that can support a deadline swing. Whether ownership is willing to support the kind of financial swing Gray would require is another matter entirely.
In Other News...
Cubs First Round Pick Already Sounds Like The Arm Fans Wanted
The Cubs spent much of the draft leaning into pitching, and their first-round choice fit that theme cleanly. With the 23rd overall pick, Chicago took Ole Miss starter Cade Townsend, a right-hander whose appeal goes beyond the usual draft buzz because he brings a varied arsenal and the kind of competitive edge teams tend to trust when they think a pitcher can move fast.
Townsend already sounds like the sort of arm Cubs fans were hoping for when the front office started stockpiling pitchers. He has the stuff to miss bats, the mentality to attack hitters, and the projection to climb quickly through the system, which matters for a club that is clearly trying to build depth before the shape of its rotation changes. The bigger question now is how soon that polish turns into production, and how aggressive Chicago will be in pushing him along. [Read more 🡒]
Cubs Suddenly Have One Deadline Problem They Cant Ignore
The Cubs have put themselves in a familiar spot near the top of the National League Central, and a playoff berth now looks like the sort of outcome that should be there for the taking. But even with October within reach, the roster still has a glaring issue that has followed the team for much of the season: the pitching staff has not been deep enough, consistent enough or healthy enough to feel secure over a full postseason push.
Chicago has gotten by despite a rotation and bullpen that have been stretched thin by injuries and uneven performance, and the front office cannot really pretend otherwise at this point. With the deadline approaching, the Cubs are in the market for help in a way that could shape not just the rest of this season but the way theyre viewed once the games get tighter, whether that means chasing a frontline arm or simply trying to patch together enough reliable innings to survive the stretch run. [Read more 🡒]
Cubs Face A Painful Deadline Call On Young Talent
The Cubs are widely expected to shop for major-league pitching at the 2026 trade deadline, and that kind of push usually comes with a cost. For a front office trying to improve a contender without emptying the system, the most realistic currency is often the group of young players who have either been squeezed by the big-league roster or built enough value at Triple-A to draw attention from other clubs.
That is where Chicagos dilemma gets a little painful. The organization has several appealing young pieces who could help bring back pitching, but the decision is complicated by fit as much as talent, with some blocked by established regulars and others forcing the issue with strong stretches in Iowa. It is the sort of deadline calculation that can shape a contender for years, because the Cubs will have to decide whether the next move is about protecting the future or using it to patch the present. [Read more 🡒]