As the 2025 MLB trade deadline approached, the Chicago Cubs found themselves in a similar situation. Sitting in contention and facing mounting expectations from a fanbase hungry for a deep postseason run that hasn’t been seen since their last trip to the NLCS in 2017. Since the beginning of July, the organization had clear needs: reinforce a rotation riddled with inconsistency, fortify a bullpen that had been overworked, and bolster a thin bench with a versatile, impact bat.
While the front office addressed all three areas, they did so in a way that left some fans confused and underwhelmed, opting for practicality over an “all-in” splash. Rather than landing headline-making stars, President of Baseball Operations Jed Hoyer and GM Carter Hawkins executed a series of calculated moves aimed at raising the team’s floor without mortgaging its future.
It took until 24 hours before the deadline for the Cubs to execute their first two deadline trades. On Wednesday, July 30, Chicago acquired back-end starter Mike Soroka (Nationals) and reliever Andrew Kittredge (Orioles) in what many thought was a prelude to something bigger on the following day.
Instead, the Cubs acquired lefty reliever Taylor Rogers (Pirates) and super utility player Willi Castro (Twins) in the final hours until the trade deadline. These acquisitions directly targeted the Cubs’ most pressing needs, even if they weren’t the flashy names floated in pre-deadline speculation.
The 27-year-old Soroka, once an All-Star with the Atlanta Braves, has quietly improved his peripherals over the past two seasons. While he may no longer profile as a frontline starter, he projects as a dependable No. 4 or No. 5 arm, an area of need for a rotation that’s lacked depth. Soroka has the ability to slot in as a long reliever once pitching reinforcements arrive or if he struggles in a starting role. Given the Cubs’ solid defense and lineup support, Soroka should thrive in Chicago. Cubs fans will find out as early as Monday, since it was announced that he would start Monday’s game at home against the Cincinnati Reds.
The 28-year-old Castro brings versatility and switch-hitting pop to a bench that has needed both for much of the season. Capable of playing multiple positions, both in the infield and outfield, Castro is the kind of glue guy teams lean on in October. His play is reminiscent of former Cub and 2016 World Series MVP Ben Zobrist. Cubs fans should expect Castro to see time in platoon roles, presumably alongside rookie Matt Shaw, while providing late-game flexibility.
In the bullpen, the Cubs have made significant strides by upgrading their high-leverage relievers. Both Kittredge and Rogers offer late-inning experience and reliability. These upgrades became possible with the corresponding DFA of Chris Flexen and Ryan Pressly, who both have had mixed results in 2025. It’s obvious the team has a lot of confidence in Daniel Palencia as their ninth-inning option, as they did not add an impact closer. They’re content with leaning on the young right-hander’s electric stuff to close out games.
The 35-year-old lefty wasted no time making an impression, delivering a clean seventh inning in his Cubs debut. Kittredge struck out two and showed the type of poise and command the team has sorely lacked in high-leverage spots.
While Porter Hodge was activated from the injured list, he was optioned to Triple-A Iowa, where he will continue to build back to full strength. His return to the MLB roster might come later this season if needed for depth or high-leverage relief. If he can figure it out and return to his 2024 dominance, the Cubs’ bullpen has the potential to lock down the final 3 or 4 innings each game.
A comeback is on the horizon with the return of Javier Assad, who many may have forgotten about after he suffered an injury during the preseason. Assad is on a rehab assignment at Iowa and is expected to rejoin the rotation in early August. Known for his poise and command, he was a steady presence in the Chicago rotation before his injury.
Assad figures to play a key role down the stretch and should slot into the middle to back half of the Cubs rotation. If he can pitch at the same level he did over the previous two seasons, they are at least six starters deep. That is a hot commodity for a potential playoff-bound time fight to the finish while saving wear and tear on your core starters.
Assad’s return, combined with Soroka’s addition and Jameson Taillon on schedule to be activated within the next couple of weeks, could provide the necessary stability and depth the Cubs have sorely needed in their rotation. All of a sudden, a rotation of Shota Imanaga, Matthew Boyd, Cade Horton, Jameson Taillon, Mike Soroka, and Javier Assad has the potential to shut down teams with an offense consistently firing on all cylinders.
Another potential difference-maker is Miguel Amaya, who is trending toward a return in the coming weeks. When healthy, Amaya offers a solid defensive presence behind the plate and a bat with emerging pop. Before his injury, Amaya was starting to put together a career year offensively and continuing to improve defensively. His return would give the Cubs another reliable catcher with offensive upside to pair with veteran Carson Kelly, who has filled in admirably, along with Reese McGuire, during Amaya’s absence.
Amaya’s ability to manage the pitching staff and contribute at the plate could provide a meaningful late-season boost to a team that has been looking for consistency behind the dish.
Many diehard fans voiced frustration at Cubs brass for not landing any of the big-name players frequently linked to Chicago in national coverage. Media outlets and pundits had been connecting the Cubs to everyone from power bats to elite arms, but those potential deals came with massive asking prices.
The truth is, the 2025 deadline didn’t offer much in the way of marquee talent, and the cost of overpaying could’ve set back what the front office is building. Hoyer and Hawkins made it clear they’re not sacrificing the future for the illusion of a quick fix.
By standing firm on their top prospects and targeting high-floor, low-risk additions, the Cubs stuck to their identity. That long-view approach is why players like Moises Ballesteros, Kevin Alcantara, Jefferson Rojas, James Triantos, Jaxon Wiggins, and Owen Caissie remain in the system. It’s also why the team’s competitive window remains wide open for years to come.
The team’s refusal to include Caissie in trade packages signals just how highly they value the lefty slugger. With rumors swirling that the Cubs will be aggressive bidders for Kyle Tucker this offseason, the front office is also preparing for the possibility that they come up short in that sweepstakes.
If the Cubs were to move on from Tucker, Caissie would be the favorite to take over in right field in 2026. Given his recent surge at Triple-A Iowa, including improved plate discipline and increased power, Caissie has boosted his stock significantly. The Cubs may consider a late-season call-up if they can get league-average defense out of him, as his bat alone may justify the move.
While the Cubs missed out on premier starters, the team could revisit a possible trade in the offseason. Negotiations involving top-tier arms like Edward Cabrera and Sandy Alcantara (Marlins) were reportedly explored but never materialized due to Miami’s sky-high asking price. Similar to the Marlins’ duo, the Nationals’ MacKenzie Gore was heavily pursued in the hours leading up to the deadline. Those conversations could resurface in the offseason, when market conditions shift and the Cubs have the flexibility to revisit bigger moves with their full slate of prospects still intact.
Coming off a difficult series against the current NL Central Milwaukee Brewers, the Cubbies enter a stretch in their schedule packed with favorable matchups. This provides them with an opportunity to chip away at their NL Central deficit until they face a pivotal five-game series with the Brew Crew August 18-21. With a bolstered bullpen, improved bench depth, and key reinforcements like Assad, Taillon, and Amaya on the horizon, the time is now to gain momentum.
If this team can build chemistry and string together wins in both August and September, there’s a clear path to overtaking the division and holding that lead through October and beyond.
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