The Chicago Cubs entered the 2026 MLB trade deadline knowing their biggest obstacle to a deep postseason run wasn’t their offense or defense it was the starting rotation. While the lineup had consistently produced enough runs to compete with the National League’s elite teams, questions lingered about whether the pitching staff could survive the pressure of October baseball.
President of Baseball Operations Jed Hoyer answered those concerns with an aggressive series of deadline moves that completely transformed the Cubs’ rotation. By acquiring veteran starters Kevin Gausman, Clay Holmes, and David Peterson, Chicago turned what had once been considered a vulnerability into one of its greatest strengths.
The changes also mean the Cubs are unlikely to find themselves relying on depth starters in critical postseason games as they did in previous years.
Veteran Colin Rea deserves enormous credit for keeping the rotation together throughout the last two seasons. Whenever injuries struck, he stepped into larger responsibilities, replacing Justin Steele after his season-ending injury in 2025 and later filling another important role when Cade Horton’s campaign was cut short early in 2026.
Rea’s durability and professionalism have been invaluable.
However, if the Cubs are playing meaningful games in October, the organization now has enough frontline pitching that Rea no longer needs to be entrusted with a winner-take-all postseason matchup.
With Holmes, Gausman, and Peterson joining the staff—and potential reinforcements expected from injured starters Ben Brown and Edward Cabrera before the playoffs—the Cubs suddenly possess the type of pitching depth required to compete for a National League pennant.
Here’s how Chicago’s postseason rotation could line up.
Game 1: Kevin Gausman
If the Cubs acquired Kevin Gausman for one reason, it was to pitch in the biggest games.
Despite experiencing an uneven 2026 regular season statistically, Gausman remains one of baseball’s most accomplished veteran starters. His track record, postseason experience, and ability to handle high-pressure situations make him the obvious candidate to start Game 1 of a playoff series.
Last season, Gausman served as the ace of the Toronto Blue Jays while helping lead the club to the American League pennant and within striking distance of a World Series championship.
That experience cannot be overlooked.
Although his traditional numbers this year haven’t fully reflected his talent, many advanced metrics suggest he has pitched better than his results indicate and could be due for improvement during the season’s final months.
He may not possess the overwhelming dominance of pitchers like Tarik Skubal, but Gausman’s combination of experience, command, and playoff pedigree makes him the ideal choice to lead Chicago’s postseason rotation.
Manager Craig Counsell would likely have little hesitation handing him the ball to open a playoff series.
Game 2: Matthew Boyd
Following Gausman with left-hander Matthew Boyd creates an immediate change of pace for opposing hitters.
Alternating between right-handed and left-handed starters has long been considered an effective postseason strategy, forcing opposing lineups to adjust from game to game.
Boyd proved last postseason that he can thrive under playoff pressure, and he enters this year’s stretch run with one important advantage—a much fresher arm.
Because injuries limited his workload earlier this season, Boyd should avoid the fatigue that affected him late last year when he logged his heaviest workload in several seasons.
His ability to generate swings and misses outside the strike zone, combined with his calm approach when facing early trouble, makes him an ideal postseason starter.
Even on nights when he doesn’t have his sharpest command, Boyd has repeatedly demonstrated the ability to settle into games and keep his team competitive.
Those qualities become even more valuable during October, when every inning carries increased importance.
Game 3: Clay Holmes
Clay Holmes may have been one of the biggest prizes available at this year’s trade deadline.
The Cubs paid a significant price by sending top-100 prospect Jefferson Rojas to acquire the veteran right-hander from the New York Mets, making it clear they envision Holmes playing a major role in their championship pursuit.
Teams don’t surrender elite prospects simply to stash newly acquired pitchers at the back of the rotation.
Instead, Holmes projects as one of Chicago’s most trusted postseason starters.
His greatest strength is his remarkable ability to generate ground balls, a skill that perfectly complements one of baseball’s strongest defensive infields.
Rather than chasing strikeouts, Holmes consistently induces weak contact, allowing his defense to convert outs efficiently while limiting damaging extra-base hits.
That formula has proven highly effective throughout his career and should translate well to postseason baseball.
Although Holmes previously built his playoff résumé as a reliever with the New York Yankees, appearing in postseason action during multiple October runs, this year could provide his first opportunity to start a playoff game.
The Cubs hope that transition will help carry them toward their first National League pennant since 2016.
Game 4: Shota Imanaga
The final rotation spot appears less certain.
If Ben Brown returns healthy before the postseason, he could certainly challenge for the fourth starting assignment. However, Chicago has exercised considerable caution throughout Brown’s recovery, making it possible the organization limits both his innings and workload if he returns in time for October.
Rather than asking the young right-hander to shoulder a full starter’s workload immediately, the Cubs could instead deploy him strategically out of the bullpen in high-leverage situations.
That possibility leaves veteran left-hander Shota Imanaga in position to round out the postseason rotation.
Imanaga has shown flashes of brilliance throughout the season, though his biggest challenge has been limiting home runs.
If he successfully keeps the ball inside the park during the final weeks of the regular season, he should retain the coaching staff’s confidence heading into the playoffs.
His experience, poise, and ability to navigate opposing lineups make him a dependable option capable of delivering quality innings when called upon.
Additional Reinforcements Could Make the Cubs Even More Dangerous
Perhaps the most encouraging aspect of Chicago’s pitching outlook is the amount of depth waiting behind the projected rotation.
If Ben Brown and Edward Cabrera both return healthy before October, the Cubs will possess several additional power arms capable of shortening games.
Combined with established relievers such as Justin Steele, Daniel Palencia, Ryan Zeferjahn, and dependable contributors like Jacob Webb, manager Craig Counsell could assemble one of the National League’s deepest pitching staffs.
That flexibility would allow Chicago to pull starters earlier, aggressively attack favorable matchups, and rely on a bullpen loaded with high-quality options throughout the postseason.
A Rotation Built for October
Just weeks ago, many viewed the Cubs’ rotation as the team’s greatest weakness.
Today, thanks to Jed Hoyer’s aggressive approach at the trade deadline, it may be the club’s greatest strength.
Adding experienced veterans like Gausman and Holmes alongside reliable arms such as Boyd and Imanaga gives Chicago a balanced rotation featuring playoff experience, swing-and-miss ability, and dependable depth.
If everyone returns healthy, the Cubs will enter October with one of the most complete pitching staffs in the National League—and perhaps their best opportunity in years to make a legitimate run at the World Series.
Leave a Reply