Building a Cubs dream pitching staff if Jed Hoyer becomes unhinged at the 2026 trade deadline

Jed Hoyer is known among Chicago Cubs fans for being a very reserved executive. He doesn't like to spend at the top of the market in free agency, and he's rarely in the market for the most elite players available even at the trade deadline. With all of that said, however, this is the year for aggression if there ever was one. The Cubs have one of the best offenses in baseball but are held back by a pitching staff held together with duct tape and bubblegum.

All signs point to the Cubs being at least somewhat aggressive in their efforts to add pitching to this team, from rumor mill to the sudden departure of Jameson Taillon from the organization. "Aggressive" can mean different things, especially when compared to the fairly quiet deadline Chicago's front office put together last year. If Hoyer decided to go in the complete opposite direction of last year, here's a look at the dream pitching staff he could build.

Trade 1: Patch up both the rotation and bullpen in a single blockbuster with the Blue Jays

The Blue Jays are perhaps the most surprising potential seller in baseball this year, given that they were just one game short of winning the World Series last year. This year, however, they're dead last in the AL East this year and will need to make some deals if they want to return to competitiveness in 2027. That leaves Chicago to pick through their pitching staff looking for assets, and they have two that could be perfect fits at Wrigley Field: Kevin Gausman and Jeff Hoffman.

Gausman is the exact sort of experienced, battle-tested veteran that this team needs. His 4.51 ERA may not look like much at first glance, but moving from Toronto's terrible defense to the Cubs' elite one should help get him closer to his peripherals (3.58 FIP). What's more, Gausman posts consistently. He's well on his way to a sixth consecutive season of making at least 31 starts, and a 2.93 ERA in last year's postseason is the exact sort of playoff experience the Cubs could use.

The 35-year-old veteran starter may be only a rental, but Hoffman could add a controllable arm to a bullpen in need of one. Hoffman's number are in a similar spot to Gausman's, with an ERA north of 4.00 covering up an elite FIP metric. He's striking out nearly 35% of his opponents this year, and is under team control for the 2027 season so Hoyer can go into next year knowing he has a dominant setup man to pair with Daniel Palencia.

Trade 2: Reunite Craig Counsell with an old friend to build a dominant bullpen

Hoffman is a great addition to the relief corps, but he had a tough year as Toronto's closer last year and has just five saves this season. Adding a proven closer to the mix as well could really set the Cubs up to have a dominating three-headed monster that any team would be terrified to face in the late innings. While a player like Mason Miller would be too ridiculous to expect for even this pie-in-the-sky exercise, there's another dominant closer who just might be available: Astros lefty Josh Hader.

Cubs fans surely remember Hader's days as an utterly dominant closer for the Brewers, and he's looking as good as ever this year with a sub-2.00 ERA and a strikeout rate approaching 40%. Hader is controlled through 2028, meaning he'd be a long-term asset for the Cubs as well. The one issue that could complicate things is his no-trade clause. Jeff Passan recently expressed doubt Hader would waive it to leave Houston, but perhaps his history with manager Craig Counsell could change that.

Trade 3: Take a big swing at a potential ace with team control

Those two trades would set the Cubs up reasonably well already, giving them a terrifying bullpen and a much-needed veteran to stabilize the rotation. But they'd do well to add more than one starter, and it goes without saying that a controlled arm would be valuable given that Shota Imanaga and Matthew Boyd are both ticketed for the open market after this year. That makes Angels southpaw Reid Detmers the perfect fit for the Cubs, and the player Hoyer should pursue most aggressively.

Detmers is controlled through 2028 and finds himself in the midst of a truly special season this year. The former top prospect has broken out in a big way, and finds him on a list of just eight pitchers who have a SIERA below 3.50 and at least 3.0 fWAR. The other seven are Jacob Misiorowski, Paul Skenes, Cam Schlittler, Dylan Cease, Cristopher Sanchez, Chris Sale, and Jesus Luzardo. That's more or less the shortlist of this year's Cy Young contenders around MLB, and Detmers has put himself in the conversation with them.

Of course, it should be noted that Detmers lacks the track record of many of those other arms. He struggled early in his career and was pitching out of the bullpen as recently as last year. Much of that, however, can be chalked up to the consistently poor defenses he's been forced to pitch in front of with the Angels and the lack of development time he had in the minors; he was pitching in the majors before the end of his first pro season.

Getting this trio of trades done would come at an astronomical cost. Virtually every prospect in the system would have to be on the table, and even young hitters at the big league level like Matt Shaw, Pedro Ramirez, and Miguel Amaya would likely have to be in the conversation if Hoyer was really going to get all of this done. That sort of aggression can pay off, however. If the Cubs did manage to add these players, they'd be one of the most fearsome teams in MLB for 2026 and beyond.

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