The Chicago Cubs entered 2026 with a clear goal in mind: to be legit World Series contenders. For the second straight offseason, the organization traded away one of its top prospects to improve the MLB roster, and for the first time in a long while, ownership dipped its toe back into the deferral game to rip Alex Bregman away from the Boston Red Sox. Now, as we get closer to the trade deadline, the Cubs have a major dilemma. Thanks to a 20-3 stretch, the Cubs have one of the best teams in MLB, but they have one giant glaring issue: starting pitching.
Yes, Shōta Imanaga has been better this year than he was during his 2024 All-Star season, and while other pitchers have stepped up in place of Cade Horton and Matthew Boyd, the Cubs need to acquire another elite pitcher to become a real threat in October.
Horton has been ruled out for the season since April, but the latest fluke injury to Boyd really set off the alarms for the Cubs. In the past week, trade rumors have been circulating around the Cubs, and it’s never been clearer where the team must upgrade to reach its World Series expectations.
Jed Hoyer will have the tough task of balancing the future with capitalizing on what appears to be a very good 2026 Cubs team. Last year, the asking prices at the trade deadline for starting pitching were ridiculously high, leading to most of the top arms staying put. Will Hoyer push the chips in this summer?
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Let’s take a look at three categories of trade targets that the Cubs have or will certainly be interested in leading up to the trade deadline. First, the rentals, the pitchers who you’re only getting for the rest of 2026 before they become a free agent. We’ll get to the following categories in subsequent articles: the guys who come with some control beyond 2026, but at a higher salary and the younger pitchers, who have been good so far this year, and are under team control for multiple years, which means the price will be a lot higher.
Rental Trade Targets
Freddy Peralta:
Age 29, 3.10 ERA, 23.8 K%, 9.0 BB%, 3.69 FIP, 3.71 xFIP
2026 salary: $8 million
2x All-Star, career 3.56 ERA in 220 games
5th in Cy Young Voting (2025 NL)
Postseason: 9 G, 6 GS, 4.32 ERA, 1.02 WHIP, 33.1 IP, 41 K
Robbie Ray:
Age 34, 2.76 ERA, 26.1 K%, 10.0 BB%, 4.52 FIP, 4.15 xFIP
2026 salary: $25 million
2x All-Star, career 3.90 ERA in 273 games
2021 AL Cy Young Winner (2 top-10 finishes)
Postseason: 6 G, 2 GS, 7.43 ERA, 1.43 WHIP, 13.1 IP, 19 K
Kevin Gausman:
Age 35, 3.86 ERA, 23.0 K%, 4.3 BB%, 3.29 FIP, 3.42 xFIP
2026 salary: $23 million
2x All-Star, career 3.82 in 371 games
3rd in Cy Young Voting (2023 AL, 3 top-10 finishes)
Postseason: 14 G, 8 GS, 3.83 ERA, 1.01 WHIP, 56.1 IP, 56 K
The American League has been brutal so far in 2026, so despite the Toronto Blue Jays starting Wednesday with a record of 18-24, they’re 2.5 games back of a Wild Card spot. Yet, if they continue to stumble, then Kevin Gausman should 100% be on the Cubs’ radar. He’s been a steady force in the rotation and has quietly been a top-tier starting pitcher for much of his career.
Meanwhile, the hottest name attached to the Cubs this past week has been Freddy Peralta. He obviously has the Craig Counsell connection as the two overlapped with the Milwaukee Brewers from 2018-23. The New York Mets have been awful, but they might not sell until the very end because they’ve invested heavily in this year’s roster. Still, Peralta will obviously be at the top of this summer’s trade target list not only for the Cubs, but for any pitching-needy contender.
Going out West, Cubs fans have been circling Logan Webb, but the more realistic trade target may ultimately be Robbie Ray. He has a higher salary, is a rental, and the left-hander has been great since returning from his 2023 Tommy John surgery. By the way, Ray being a lefty may also be intriguing for the Cubs, who have had no issues loading up their rotation from that side in their contention window.
We talked about these guys and more in this week’s Pinwheels And Ivy Podcast. The Cubs are good this year, but the big question remains: Will they go all-in at the trade deadline?
