The Cubs have spent this season swinging between extremes, and that has left their trade deadline outlook just as unsettled. They dropped 10 straight, then ripped off 10 wins in a row, and more recently turned in some eye-popping offensive showings against the San Diego Padres. Even with all that volatility, they still sit 5.0 games behind the Milwaukee Brewers in the NL Central with three months left.
That gap matters because the next month could decide whether Chicago approaches the deadline with urgency or caution. MLB.com’s Mark Feinsand laid out the possibility that Jef Hoyer and the Cubs could take a familiar, low-key path again if they don’t believe they can reel in Milwaukee.
“Last summer, the Cubs made four trades to bolster their depth rather than making any headline-grabbing moves,” Feinsand writes. “Unless Hoyer believes his club can challenge the Brewers for the NL Central title (and, perhaps more importantly, that first-round bye), we could see a repeat of that approach in 2026.”
That was the script a year ago, when Chicago added Andrew Kittredge, Michael Soroka, Willi Castro, and Taylor Rogers. Useful pieces, yes. Splashy moves, no.
This time, the pressure point is obvious. The Cubs have clear needs in both the starting rotation and the bullpen, and the market could include big names such as Tarik Skubal and Freddy Peralta. But if Hoyer doesn’t think this club can catch the Brewers and lock down that first-round bye, the deadline could again be more about depth than drama.
That would be a frustrating outcome for a team that still has the kind of upside to matter in October. A stronger push in July could change the picture quickly, especially if Milwaukee slips and Chicago climbs back into position for that bye. If that happens, the deadline could become a lot more interesting.
In Other News...
Brewers Suddenly Face A Roster Decision On A Familiar Pitcher
Jake Woodfords return to the Brewers organization has quickly turned into another roster crossroads. The right-handed reliever, who was designated for assignment in early June, cleared waivers, elected free agency and then came back on a minor league deal, but his season has not given Milwaukee much reason to feel locked in one direction.
Woodford has struggled in both the majors and at Triple-A this year, and now the contract he signed gives the Brewers a decision they cannot avoid for long. If they do not add him to the big-league roster, the alternative would leave them without much control over what happens next, which is exactly the kind of late-summer bullpen wrinkle teams prefer not to have hanging over them. [Read more 🡒]
Brewers Suddenly Have One More Deadline Question In The Outfield
The Brewers are already expected to be busy before the Aug. 3 trade deadline, with bullpen help, a top-tier starter and a left-side infield answer all on the shopping list. But the more this lineup is examined, the clearer it becomes that the outfield may need a look too, especially with Milwaukee leaning heavily on left-handed bats in a season where left-on-left matchups have been a problem.
A right-handed hitting outfielder would give the Brewers another way to patch that split, whether the answer comes from the farm system or from the trade market. Prospect Luis Lara has given the organization something to think about with strong production against left-handers in the minors, and the front office will have to decide whether internal depth is enough or whether this is another spot that needs to be addressed before the deadline clock runs out. [Read more 🡒]
Brewers Face A Brutal Jacob Misiorowski Decision As Stakes Rise
Jacob Misiorowski has become one of the most compelling stories in the National League, and the Brewers are now staring at the kind of decision every contender hopes to avoid. With the rookie right-hander in the mix for the NL Cy Young Award, Milwaukee has to weigh the value of pushing for individual hardware against the bigger priority of keeping his arm fresh for the stretch run.
That tension is what makes the second half so tricky. Misiorowskis workload has already climbed into territory that demands attention, and the Brewers know a cautious approach could leave him short of the volume that tends to sway award voters, especially when other top starters are piling up innings. For Milwaukee, it is a familiar front-office and dugout balancing act, but this one carries a little more weight because the upside is so obvious and the margin for error is so thin. [Read more 🡒]