As Major League Baseball resumes after the All-Star break, optimism remains high around the Chicago Cubs despite a tightly contested National League playoff race. With 66 games left on the schedule, the Cubs are well-positioned to make a serious postseason push, and several intriguing storylines could shape the remainder of their 2026 campaign.
After making a set of preseason predictions back in January, some of which are still alive, attention has now shifted to what could unfold over the final stretch of the regular season. Here are five bold predictions that could define Chicago’s second half.
Ben Brown Could Return as a High-Leverage Co-Closer
One of the biggest boosts the Cubs may receive in the coming weeks is the anticipated return of right-hander Ben Brown. Manager Craig Counsell recently indicated that Brown is close to beginning mound work and hinted that, once healthy, he could fill an “out-getter” role—a versatile relief assignment that allows him to pitch in critical situations throughout a game.
Rather than returning to the starting rotation immediately, Brown could emerge as a co-closer alongside Daniel Palencia, who is also working his way back from injury. Sharing late-inning duties would help reduce the workload on both pitchers while giving the Cubs another dynamic weapon in high-pressure situations.
If both relievers regain full health, Chicago’s bullpen could become one of the National League’s strongest during the playoff race.
Dansby Swanson May Reach a New Career Home Run Mark
After enduring one of the worst offensive slumps of his career earlier in the season, shortstop Dansby Swanson has completely transformed his production since mid-June.
Over his last 22 games, Swanson has been one of baseball’s hottest hitters, batting .310 while posting a remarkable .702 slugging percentage with nine home runs. His resurgence has raised his season total to 17 long balls.
With more than two months remaining, Swanson needs just 11 additional home runs to establish a new personal best of 28. If he maintains anything close to his current pace, reaching the 30-home-run milestone is no longer unrealistic.
A productive Swanson could provide much-needed offensive depth behind stars like Pete Crow-Armstrong and Alex Bregman as the Cubs chase a division title.
Alex Bregman Could Finish Strong Despite Earlier Setbacks
Veteran infielder Alex Bregman has battled inconsistency this season, but history suggests a second-half surge is well within reach.
From 2022 through 2025, Bregman consistently averaged more than 20 home runs annually while maintaining an OPS above .800, even during an injury-shortened campaign.
If he remains healthy and appears in roughly 60 of the Cubs’ remaining games, Bregman has a realistic opportunity to finish the season with at least 20 home runs and an OPS above .800. Achieving those numbers would represent another impactful offensive boost for Chicago during the final playoff push.
His postseason experience and veteran leadership could become increasingly valuable as the pressure intensifies.
Chicago Could Target Reid Detmers Before the Trade Deadline
With the MLB trade deadline approaching, the Cubs are expected to remain aggressive in strengthening their pitching staff, and one intriguing target could be Los Angeles Angels left-hander Reid Detmers.
At just 27 years old, Detmers fits the profile of the type of controllable pitcher president of baseball operations Jed Hoyer has frequently pursued. He remains under team control beyond this season, carries an affordable salary, and has shown flashes of frontline potential.
Although Detmers struggled early in 2026, he rebounded with an impressive seven-start stretch during May and June, posting a 2.42 ERA, a 2.79 Fielding Independent Pitching (FIP), and an outstanding 0.783 WHIP. He has also limited walks while doing a solid job keeping the ball in the park.
Adding Detmers would strengthen Chicago’s rotation heading into October and provide another quality left-handed option capable of handling postseason innings.
The Cubs Could Finish with 94 Wins, Capture the NL Central, and Earn a First-Round Bye
Perhaps the boldest prediction centers on the Cubs’ overall finish.
Chicago enters the second half with a 54-42 record and would need to finish 40-26 over its final 66 games to reach 94 victories. While that pace is ambitious, it is far from impossible considering the Cubs have gone 20-8 since June 10, producing the best record in Major League Baseball during that span.
Their recent surge has coincided with improved pitching, timely hitting, and consistent contributions throughout the lineup.
Meanwhile, division rival Milwaukee enters the second half after dropping four of its final five games before the All-Star break while also dealing with several pitching injuries. If the Brewers cool off and Chicago maintains its current momentum, the Cubs could overtake them atop the National League Central standings.
Winning the division with 94 victories could also be enough to secure one of the National League’s top two seeds, earning a valuable first-round bye and allowing the club extra time to prepare for the Division Series.
If these predictions come true, the Cubs would enter October not simply as playoff participants but as legitimate World Series contenders with one of the National League’s deepest and most balanced rosters.
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