As Tarik Skubal‘s trade rumors get brighter, the Chicago Cubs’ current scene with their rotation makes them one of the suitors in his race. With names like Matthew Boyd, Cade Horton, and Justin Steele on the injured list, it sparks a need for another reliable starter by the trade deadline. However, just as the Cubs shot up their payroll from the last year in landing Alex Bregman, MLB insider Ken Rosenthal wonders if it is feasible anymore for the franchise to make another big-ticket purchase.

“I don’t know how much willingness there will be from the Cubs to boost the payroll when they’ve already done it,” Rosenthal said via Foul Territory.

The Cubs’ 2025 payroll was around $214 million. They went further and splashed $175 million on Alex Bregman, who recorded just 5 homers so far. So, already the Cubs are facing a negative ROI from their third biggest contract ever in the franchise’s history. This serves as a stark reality check about whether they should proceed and further up their payroll for Skubal.

Skubal is not a budget-friendly option. He just underwent surgery to remove loose bodies in his left elbow, but it didn’t reduce the value of the reigning AL Cy Young winner. “The morning the latest surgery was announced, I was texting those same people as part of an industry straw poll on what Skubal’s contract would be. Seven of them got back to me before the news broke. The average of those projections was 7.7 years for $357 million, or just over $46 million per year,” ESPN’s Kiley McDaniel noted.

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With such a projected amount, the Cubs need to splash 2 times of what they offered to Bregman. We also wonder if they would take that risk.

The Cubs are currently ranked 19th in terms of ERA (4.29). Apart from Steele, Horton, and Boyd’s injuries, Jameson Taillon landed on the injured list with a hamstring strain. It just compounded the matter as he has struggled with a 5.19 ERA and an increasing number of home runs allowed. Shota Imanaga is also experiencing a rough stretch in his 2026 campaign, carrying a 4.74 ERA through 13 starts. These prove that Skubal’s rumors with the Cubs make sense.

Since Skubal’s bitter arbitration battle with the Detroit Tigers early this year, their divorce is on the line. Now, with a 27-39 record, the Tigers have no choice but to give up on Skubal, which could bring a few prospects on board. And with an above-$350 million projection, the Tigers’ hold over Skubal is surely loosening. It could have been the best chance for the Cubs, but their reality says otherwise.

The Cubs’ rough patch with trading chips doesn’t end with Skubal.

The Cubs have a few more concerning updates

Financial reality could also block the Cubs from contending for Freddy Peralta. After Skubal, Peralta might be the most popular arm rumored to be a trade chip. The Mets are reportedly willing to give up on his rental year, and he is also not coming cheap. “If a team acquires New York Mets ace Freddy Peralta at the trade deadline and wants to keep him, they better be ready to pay up. Peralta will be seeking a free agent contract similar to Max Fried’s eight-year, $218 million deal, according to those familiar with Peralta’s expectations,” Bob Nightengale predicted.

We are uncertain if Jed Hoyer would be willing to spend such after giving up $35 million AAV to Bregman. With a 3.63 ERA, Peralta is leading the rotation with the Mets and could play a similar role with the Cubs. Apart from the financial constraint, the Cubs’ dwindling farm system is making things worse.

The Cubs’ farm system was ranked No. 2 in 2024. It crashed down to No. 23 this year. Hence, it would be difficult for the Cubs to offer an attractive exchange bid for Peralta or Skubal, especially when the Dodgers are in the race. Still, baseball means surprises, and a Bregman-like sweep could be on the table.