The Chicago Cubs made a series of aggressive moves in the final hours leading up to Monday’s Major League Baseball trade deadline, signaling a clear commitment to bolster their pitching staff and make a sustained postseason push. Currently holding the top National League wild-card position, the Cubs’ front office completed four trades within a 36-hour span, acquiring multiple pitchers and an outfielder to reinforce a roster entering the final stretch of the regular season.

Cubs president of baseball operations Jed Hoyer emphasized the uniqueness of each trade deadline and the organization’s confidence in the team’s resilience. “We felt like we did the things that would honor that and reinforce the roster over the next 50 games,” he said, reflecting on the club’s decision to invest heavily in pitching.

The incoming players include right-handed pitchers Clay Holmes from the New York Mets and Kevin Gausman from the Toronto Blue Jays, reliever Ryan Zeferjahn from the Los Angeles Angels, left-hander Braxton Garrett from the Miami Marlins, and outfielder Tyrone Taylor also from the Mets. Zeferjahn and Garrett are under team control beyond the current season, providing the Cubs with longer-term options.

To complete these transactions, Chicago parted with several prospects, including former top prospect Moisés Ballesteros and two top 10 prospects—shortstop Jefferson Rojas and first baseman Jonathon Long—along with three additional prospects ranked 13-21 overall. These departures underscore the organization’s willingness to trade potential future assets to enhance its current roster.

While the Cubs had aimed to acquire a controllable starting pitcher similar to their pursuit in last year’s trade deadline, Hoyer acknowledged that negotiations never advanced to a close. The top available pitcher the Cubs could realistically secure was left-hander Tarik Skubal. Despite discussions with Detroit Tigers personnel, the Tigers eventually traded Skubal to the Los Angeles Dodgers, where he is set to make his debut at Wrigley Field on Tuesday. Hoyer regarded the Tigers’ move as strategically sound, acknowledging the value they received in return.

The additions of Gausman and Holmes represent significant upgrades amid injury challenges in Chicago’s pitching staff. With four would-be rotation members sidelined, the Cubs are facing depth concerns; right-hander Edward Cabrera is expected to return this month. Although it remains uncertain when Gausman or Holmes will join the rotation, the team has optioned Garrett to Triple-A Iowa, where he can provide starting pitching depth now and in future seasons.

Holmes presents the biggest question mark, having been out since mid-May due to a fibula fracture. He recently completed a third rehabilitation outing, throwing 73 pitches, but the Cubs plan to confer with him about the best path forward before activating him from the 60-day injured list.

Hoyer characterized the trade deadline as a “matchmaking game,” explaining that the deals with Toronto and New York materialized because the Cubs’ prospects aligned well with those teams’ needs. Chicago’s objective is to chase down the division-leading Milwaukee Brewers, potentially securing a top-two National League seed that would grant them a bye into the NL Division Series. The Cubs and Brewers face each other seven more times this season, including a critical stretch from August 31 to September 9.

While recognizing the challenge posed by the Brewers’ strong position, Hoyer expressed confidence in the reinforced pitching staff and the team’s ability to meet the challenge in the season’s final weeks.