The MLB trade deadline always brings its share of blockbuster moves, but the Chicago Cubs are cooking up something that could shake the entire NL Central. They’re eyeing Paul Skenes’ $77 million teammate—a proven ace who’s been quietly dominating while playing second fiddle to baseball’s most hyped rookie. With just a few days left before the July 31 deadline, the Cubs are making a serious noise about landing this starter, who could completely transform their rotation. Any guesses who’s got their attention?

The buzz centers around Pittsburgh Pirates ace Mitch Keller, the $77 million right-hander who’s been dealing with this season. Multiple reports suggest the Cubs are willing to include their top prospect, Owen Caissie, in a potential trade package for Keller, creating a fascinating chess match between division rivals. The 23-year-old Canadian outfielder has been tearing up Triple-A Iowa with a ridiculous .951 OPS and 19 homers through 73 games. Tbh, it makes sense. When you’re sitting on baseball’s prospect according to MLB.com, you’ve got the ammunition to make serious moves.

Bob Nightengale of USA TODAY has been all over this story, providing the most detailed reporting on the Cubs’ aggressive pursuit. “The Cubs desperately want another starter at the deadline, targeting Mitch Keller of the Pirates, and would include outfield prospect Owen Caissie to make it work,” he wrote recently. His sources consistently point to the Chicago front office viewing this as their best shot at landing a controllable starter who could anchor their rotation for years to come.

But here’s where this potential trade gets really interesting. This isn’t the first time Caissie’s name has surfaced in major trade discussions this season. Chicago won’t sacrifice their surging prospect for rental players, especially after Caissie’s explosive Triple-A turnaround that sees him crushing pitches nightly while cutting strikeouts. Since May 21, he’s slashing .315/.407/.635 with a 163 wRC+ and improved 25.8% strikeout rate.

However, the Pirates’ ace isn’t a rental—he’s locked up through 2028 for $55 million. The 29-year-old right-hander delivers career-best numbers: 3.53 ERA, 3.42 FIP, both significantly above league average. Keller manages contact rather than dominates with strikeouts, a profile that succeeds for Chicago but carries playoff risk.

But wait—there’s a plot twist brewing that could derail this entire trade saga. The Cubs might already have their rotation savior warming up in the wings.

Cubs’ Javier Assad’s return could change everything

While the Cubs chase external solutions, they’re also banking on internal reinforcements that could shift the entire deadline calculus. Javier Assad will take the mound for a crucial rehab start Wednesday with Triple-A Iowa, determined to shake off the nightmare oblique injury that has haunted him since spring training. His potential return creates a fascinating subplot to Chicago’s aggressive trade pursuit: Why mortgage the future when help might already be coming home?

Assad’s injury saga reads like a cruel joke that’s tested everyone’s patience. He injured himself during spring training, then re-aggravated the left oblique during an April rehab start with Iowa, creating a frustrating cycle of false hope and setbacks. “Just trying to get back to my 100 percent,” Assad said Saturday through a translator, his 28th birthday looming on the same day as his potential comeback. Thursday’s three scoreless innings in the Arizona Complex League suggest he’s finally turning the corner, throwing strikes with conviction.

Manager Craig Counsell sees Assad as a difference-maker down the stretch, someone who could drastically alter their trade deadline approach. “It’s been a tough season for Javy in terms of, you know, he was really injured most of spring training and his entirety of the season,” he said with obvious relief.

The Cubs desperately need Assad’s return as their rotation blueprint crumbles with each passing week. Justin Steele finished his season after elbow surgery, though Jameson Taillon’s calf strain recovery offers hope for stability. At 61-43 and tied atop the NL Central with Milwaukee, Chicago’s playoff push could hinge on Assad’s health more than any blockbuster trade. His numbers—7-6 with a 3.73 ERA across 29 starts—prove his value when available.