All eyes are on the Chicago Cubs with the trade deadline looming. 

The Cubs will be very active trying to acquire multiple pitchers at the deadline. They need some rotation and bullpen help for the stretch run. The North Siders are said to be looking for three total pitchers by Monday’s trade deadline. That could include one starting pitcher and two relievers, or two starting pitchers and one reliever. 

After the Los Angeles Dodgers traded three prospects for Tarik Skubal late on Saturday night, the Cubs need to have the perfect trade deadline. These three moves could improve Chicago’s chances of making a deep postseason run. 

The Cubs want controllable starting pitching. They would get exactly that by trading for Los Angeles Angels starting pitcher Reid Detmers. Detmers is 27 years old and won’t be a free agent until after the 2028 season. 

Although Detmers has a 4.03 ERA across 125 innings pitched this season, his expected numbers look a whole lot better than his actual numbers. The southpaw has a 3.38 expected ERA, 3.35 FIP, and a 3.58 expected FIP. Those solid expected numbers go with a strong 32.3% chase rate, 29% whiff rate, and a 28.3% strikeout rate. 

Detmers would be a solid get for the Cubs. He’s still on the younger side and has shown his potential on the mound throughout the 2026 season. With the Angels reportedly in the market for a catcher, Owen Ayers could headline the return to Los Angeles. 

Cubs Receive: Reid Detmers

Angels Receive: Owen Ayers (No. 3), Kane Kepley (No. 5), Mason McGwire (No. 19)

The Cubs need more than one starting pitcher at this year’s trade deadline. After missing out on both Tarik Skubal and Freddy Peralta, Chicago’s front office pivots to another starting pitcher on an expiring contract. 

Toronto Blue Jays starting pitcher Kevin Gausman is not having the best season on the mound. He has a 4.38 ERA, 1.288 WHIP, and 127 strikeouts across 127 ⅓ innings pitched. Gausman also has a 5.86 ERA over his last 11 starts dating back to the beginning of June. 

But Gausman is exactly the type of pitcher the Cubs need in their rotation for the stretch run. He’s an experienced veteran who has posted solid playoff numbers in the past. In last year’s Blue Jays postseason run, the right-hander had a 2.93 ERA across 30 ⅔ innings. 

Cubs Receive: Kevin Gausman

Blue Jays Receive: Dominick Reid (No. 14), Pierce Coppola (No. 29)

Not only is starting pitching a big need for the Cubs, but so is bullpen help. Grabbing at least one high-leverage arm is a must. Luckily, there are plenty of valuable relief pitchers who are expected to be moved in the coming hours. 

The front office could go after controllable bullpen arms like Luke Weaver or Jeff Hoffman. However, the prices on those pitchers won’t be low. Instead, Chicago pivots to Adrian Morejon, who is a top left-handed reliever. Morejon has a 3.07 ERA and 67 strikeouts across 58 ⅔ innings pitched. 

Since he will be a free agent at the end of the 2026 season, the asking price for him won’t be as high as that of relievers like Weaver or Hoffman. 

Cubs Receive: Adrian Morejon 

Padres Receive: Jordan Wicks, Ty Southisene (No. 13), Grant Kipp (No. 28)