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The Chicago Cubs have emerged as one of the National League’s most formidable teams in 2025, boasting a dynamic offense and a stronghold on the NL Central. Yet, beneath the surface of their impressive record, several key players have failed to meet expectations, raising concerns about the team’s ability to sustain its success into October. With the postseason in mind, let’s examine the three most disappointing Cubs so far this season and the impact their struggles have had on an otherwise surging club.
Ian Happ is Inconsistent at the Top
Ian Happ entered 2025 as a crucial piece of the Cubs’ offensive puzzle, expected to set the table as a leadoff hitter and provide a steady presence in the outfield. However, his season has been defined by frustrating inconsistency. After a sluggish start, Happ briefly caught fire, raising his average to .274, only to fall back into a prolonged slump that has left fans and coaches exasperated. As of late May, Happ is hitting .256 with three home runs, 21 RBIs, and 35 runs scored, but his production has been streaky at best. He has managed just one hit in his last five games, underscoring his inability to maintain momentum at the plate.
Happ’s on-base skills are vital for a Cubs lineup that ranks among the league leaders in runs and power categories, but his unpredictable performance has often left the offense searching for a spark. When Happ is getting on base, the Cubs’ run-scoring machine operates at full throttle. When he’s cold, the lineup can look surprisingly ordinary. The Cubs have thrived despite his inconsistency, but as the season wears on and the stakes rise, Chicago will need Happ to rediscover the reliable approach that made him a mainstay atop the order. His struggles are particularly glaring given the team’s overall offensive prowess, and a turnaround from Happ could elevate the Cubs from contenders to true World Series favorites.
Ryan Pressly Struggles in the Bullpen
The Cubs’ bullpen has been a source of anxiety for much of 2025, and the struggles of veteran reliever Ryan Pressly have only exacerbated those concerns. Signed to bring stability and late-inning dominance, Pressly has instead delivered a rocky campaign. Through nearly two months, Pressly owns a 4.95 ERA with four saves and a negative WAR, a far cry from the shutdown closer the Cubs envisioned when they acquired him. His May performance has been particularly troubling, as he’s posted a 21.60 ERA without recording a single save and 2 losses. One disastrous outing against the Giants, in which he allowed eight earned runs, has inflated his season numbers, but even excluding that meltdown, Pressly’s inconsistency has been alarming.
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Pressly’s inability to lock down leads has forced manager Craig Counsell to shuffle roles in the bullpen, creating instability in high-leverage situations. The Cubs have blown seven leads this season, and while not all can be pinned on Pressly, his struggles have been emblematic of a bullpen that lacks a true anchor. With the trade deadline approaching, Chicago may be forced to seek outside help if Pressly cannot regain his form. For a team with championship aspirations, the margin for error is slim, and Pressly’s disappointing season looms large as the Cubs eye a deep playoff run.
Ben Brown is the Rotation’s Weakest Link
While the Cubs’ rotation has held up admirably despite injuries to key starters like Shota Imanaga and the season-ending loss of Justin Steele, Ben Brown has emerged as the most disappointing member of the staff. Brown’s season has been marked by inconsistency and an inability to navigate opposing lineups multiple times through the order. He currently sports a 3-3 record with a 6.39 ERA over 10 starts, numbers that reflect both his potential and his persistent struggles.
Brown has shown flashes of promise, occasionally dominating through the early innings of games. However, he has repeatedly faltered as games progress, often unraveling in the middle frames. A recent outing against the Phillies exemplified this trend: after cruising through six strong innings, Brown imploded in the fourth, surrendering six earned runs. This pattern of laboring through tough innings and failing to make necessary adjustments has limited his effectiveness and put additional strain on the bullpen.
With the rotation already stretched thin by injuries, the Cubs have little choice but to keep sending Brown to the mound. However, if he cannot find a way to pitch more efficiently and limit damage the second and third time through the order, his spot in the rotation could become a liability as the postseason approaches. The Cubs’ front office may need to explore trade options to bolster the staff if Brown’s struggles persist, especially with the team’s sights set firmly on October baseball.
