The prospect cost was likely going to be high if Chicago Cubs president of baseball operations Jed Hoyer and the front office invested in upgrades to a roster currently holding the top National League wild-card position.
Hoyer deemed a deliberate investment in this Cubs team was warranted, backed by four trades in the 36 hours leading up to Monday’s MLB trade deadline. Their focus was clear: pitching, pitching and more pitching.
“Every season is different at the deadline, it is never quite the same,” Hoyer said. “This year we had really clear goals based on how the team has played and certainly the resilience this team has shown has been really special, and so I think we did the things that we felt like would honor that, and would reinforce the roster over the next 50 games. The way the season has gone, that was something that was really important.”
The Cubs added right-handers Clay Holmes (New York Mets) and Kevin Gausman (Toronto Blue Jays), reliever Ryan Zeferjahn (Los Angeles Angels), left-hander Braxton Garrett (Miami Marlins) and outfielder Tyrone Taylor (Mets). Zeferjahn and Garrett are under team control beyond this season.
The haul required the Cubs to give up former top prospect Moisés Ballesteros, two of their top 10 prospects in shortstop Jefferson Rojas and first baseman Jonathon Long, three prospects in the Nos. 13-21 range — outfielder Brett Bateman, right-hander Mason McGwire and middle infielder Ty Southisene — and minor-league pitcher Jace Beck.
If there was any question as to whether the front office believes this Cubs team can do damage in the postseason, their trade deadline moves should quell those thoughts. The Cubs were aggressive buyers in a way they haven’t been in years.
Chicago Cubs president Jed Hoyer speaks to members of the media following the MLB trade deadline, before a Monday night game against the Los Angeles Dodgers on Aug. 3, 2026 at Wrigley Field. (Arthur Maiorella/Chicago Tribune)
“Ideally, you don’t trade prospects, but at the same time, we’re here to win,” Hoyer said. “We’re here to make this roster better. We’ve invested a lot in this roster, not just financially, but in terms of how we put the roster together. It’s a really good team, and so I think that’s part of being in contention and being in a good position.
“We felt like those were some areas that we could afford to trade from, and that’s part of the deadline, you’re going to trade away real talent. But our team is in a good position, and we wanted to really reinforce the roster.”
The Cubs would have preferred to land a big-league controllable starting pitcher, something they also pursued last trade deadline when the prices were ultimately too high. The Cubs talked to a lot of teams about their controllable starting pitchers, but “candidly we never got very close on that,” Hoyer said.
Left-hander Tarik Skubal was the best arm the Cubs could have landed among those traded. Detroit Tigers president of baseball operations Scott Harris and Hoyer’s relationship goes back years to when Harris spent seven seasons in the Cubs’ front office. Asked if the Cubs made an offer to the Tigers for Skubal, Hoyer said, “We had a lot of conversations.”
The Tigers sent Skubal to the Dodgers, and the back-to-back American League Cy Young Award winner will make his debut with Los Angeles on Tuesday at Wrigley Field.
“The Dodgers have done a fantastic job in player development, they have a really good farm system, and (Harris) did the best thing he could do for the Tigers and got a lot of talent back,” Hoyer said. “I know there’s been a reaction around baseball about it, but they put themselves in position to do that deal, and they did, and that’s exactly what they should be doing.”
Adding right-handers Gausman and Holmes is a significant upgrade for a pitching staff that has four would-be members of the rotation on the injured list, though right-hander Edward Cabrera is nearing a return this month. The Cubs don’t know yet when Gausman and Holmes will slot into the rotation. Garrett was optioned to Triple-A Iowa were he provides starting depth and gives them another starter option in 2027. At some points over the final two months, the Cubs could deploy a six-man rotation, manager Craig Counsell said, but it’s not expected to be a prolonged, regular setup because of the stress it would put on the bullpen.
Chicago Cubs catcher Moisés Ballesteros rounds the bases after hitting a home run in the third inning against the Arizona Diamondbacks at Wrigley Field on May 3, 2026. (Eileen T. Meslar/Chicago Tribune)
Holmes is the bigger question mark at the moment. He hasn’t pitched since mid-May due to a fibula fracture but reached 73 pitches Sunday in his third rehab start. The Cubs want to sit down with Holmes once he reports to the team to discuss whether he wants another rehab outing or if he’s ready to come off the 60-day injured list to start for the Cubs.
When the Cubs learned Friday into Saturday that the Blue Jays would indeed be willing to move Gausman, his experience, big-league success and postseason performance made him a clear target and ideal fit.
“The trade deadline is such a matchmaking game,” Hoyer said. “It’s, who likes your prospects? How do you line up? There’s teams you just don’t line up with, and it’s very obvious right away that you know this person that you’re getting connected with over and over is not going to happen, and that happens. It felt like with Toronto and New York, it felt like we had matches, and that’s how deals get done.”
The Cubs’ deadline moves have the chance to become more impactful in the postseason if they’re able to chase down the division-leading Milwaukee Brewers and secure a top-two seed in the National League to get a bye to the NL Division Series. The division rivals face each other seven more times between Aug. 31 and Sept. 9.
“We have a pitching staff that’s more reinforced, but they’re a really good team, and the pressure is on us,” Hoyer said. “We’ve had a good stretch so far, but they’re in a good position. So we have to play really well to track them down. It’s a great goal to try to do it, but they put themselves in good position.”