CHICAGO — The MLB trade deadline is just eight days away.
The Cubs aren’t approaching it in a crisis, so to speak, but things are certainly different than they were in June.
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Mere weeks ago, Craig Counsell’s men were cruising atop the National League Central with a 6.5-game lead over the division at their peak.
Then, the Milwaukee Brewers’ unprecedented 11-game winning streak snatched that lead from their I-94 neighbors for the first time since April 4.
The Cubs’ 3-3 homestand culminating in an 8-4 loss to the Kansas City Royals on Wednesday only amplified their needs at the deadline, but a few insiders believe a big splash is brewing on the North Side.
One of them is MLB analyst Jim Bowden, who compared Cubs president of baseball operations Jed Hoyer’s 2025 playbook to Theo Epstein’s 2016 World Series-winning season.
“I think they’re going to be aggressive,” Bowden said on Foul Territory Network’s “North Side Territory.” “One of the things that Jed Hoyer was talking about when he hired Counsell was when he went back and reflected on when they hired Joe Maddon and won the World Series. That was kind of the thinking when they went from David Ross to Craig Counsell.”
Bowden referenced the deal Epstein and the Cubs did at the 2016 trade deadline when they acquired high-octane reliever Aroldis Chapman in exchange for four prospects, including then-No. 1 prospect Gleyber Torres.
“I think that blueprint is exactly what Jed is planning,” Bowden said. “I’ve heard too many opposing GMs mumbling (Cubs No. 1 prospect) Owen Caissie. I’ve just heard his name over and over again.”
Caissie has surged to the top of the Cubs’ prospect list with a Triple-A season that’s seen him hit .282 with 20 home runs and a .964 OPS.
He’d almost certainly be the main offering in any major deal the Cubs make, especially as they make starting pitching their priority.
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A number of names have floated in the Cubs’ vicinity including the Pittsburgh Pirates’ Mitch Keller, whom Bowden said he kept hearing would be dealt to Chicago for Caissie.
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“It made a lot of sense to me from both sides,” Bowden said. “The Cubs get that starting pitcher in the rotation and the Pirates get a much-needed power bat.”
No such deal between the Cubs and Pirates has materialized, but new names are entering the conversation every day — one being a pitcher the Cubs traded near the deadline eight years ago.
ESPN’s Buster Olney reported Wednesday that San Diego Padres righty Dylan Cease is being shopped, and the Cubs are an interested party.
A surprise name has emerged in the starting pitcher market: Dylan Cease, who will be eligible for free agency at year’s end. Perception of other teams is that the Padres are intent on making a push for the playoffs, and would use Cease to help fill other roster needs. Mets, AL…
— Buster Olney (@Buster_ESPN) July 23, 2025
Cubs fans may remember when Cease, the organization’s No. 4 prospect in 2017, was part of a deal with the White Sox that landed the Cubs Jose Quintana. Cease headed to the South Side and made his MLB debut in 2019 before making his way to San Diego in a March 2024 trade with the White Sox.
Cease has a modest 3.90 ERA over his season and a half with the Padres, but has made some lofty achievements, including the no-hitter he threw on July 25 of last year.
There’s no further information on whether the Cubs would bring their 2014 sixth-round draft pick back home. This season, he has a 3-10 record with a 4.59 ERA for the Friars, but his Fielder-Independent Pitching ERA (FIP) is over a point lower at 3.49.
Cease is also one of the league’s best at generating swing-and-miss, sitting at third in MLB in strikeouts per nine innings (11.51) and fifth in strikeout rate (30%).
The 29-year-old would be a steadfast upgrade for the Cubs in the starting rotation — especially when he can thrive in a pitcher-friendly park like Wrigley Field. However, he will be a free agent at the end of the season, and it is uncertain how much Hoyer is willing to offer for a potential rental.
The buzz at Wrigley Field is almost strictly about deadline deals as well — and even though the Cubs have yet to make a big move, neither has the rest of MLB.
“Honestly, it feels like the whole industry is not close on anything,” Counsell said of the trade deadline before Wednesday’s game. “That’s why there’s a deadline — that’s what creates the action.”
Counsell, Hoyer and general manager Carter Hawkins have remained tight-lipped on said action, but there are certainly a few Cubs who eagerly await welcoming new faces to the clubhouse as the division race heats up.
“I’m excited for the deadline for us,” third baseman Matt Shaw said with a smile on his face. “We’re a good team, and we’re going to do continuous things to try to win a World Series. That will be exciting.”