This past weekend marked a significant, albeit small, victory for the Chicago Cubs as they clinched their first series win since mid-June by taking two out of three games against the Los Angeles Angels. Despite this success, which included solid starts from the pitching staff and a spark in the team’s batting lineup, the Cubs’ season continues to linger in uncertainty.

Currently anchored at the bottom of the National League Central, the Cubs find themselves trailing the division-leading Milwaukee Brewers by a sizable eleven-game margin. However, even in their underwhelming position, the Cubs remain somewhat viable in the race for the National League’s final Wild Card spot, sitting 5.5 games behind the San Diego Padres.

The 2023 preseason was filled with promises of competition and potential dominance in their division, spurred by an overachieving previous season and the acquisition of key assets. Under the new management of Craig Counsell and bolstered by additions like pitcher Shota Imanaga and infielder Michael Busch, expectations for the Cubs were set high. The re-signing of Cody Bellinger was seen as a finishing touch on a roster primed for postseason contention.

However, as the season has unfolded, the reality has diverged significantly from those preseason aspirations. The Cubs have struggled with inconsistencies at the plate, missteps in the field, and a bullpen that has failed to find its rhythm.

The looming MLB trade deadline now poses a crucial juncture for the Cubs, who appear to be teetering on the edge of deciding whether to sell off assets or aimlessly push through the remainder. According to respected baseball analyst Jeff Passan of ESPN, the Cubs find themselves precariously positioned in what he describes as “no-man’s land.” With limited desirable talent to offer, and little justification to make buying moves, them finding meaningful trade opportunities appears challenging.

Passan suggests that executive decisions at this point are crucial, although Cubs President of Baseball Operations Jed Hoyer was only mentioned as an honorable mention in his discussion of front office execs with the most at stake. Hoyer’s tenure, which began in 2020, might be subjected to increased scrutiny as the trade deadline approaches.

Players like Cody Bellinger, who has reportedly garnered interest from teams such as the Philadelphia Phillies, Jameson Taillon with his appealing contract, and others like Ian Happ and Nico Hoerner, are circulating in trade rumors. Their potential moves could signal a strategic shift for the Cubs as they assess their directions for this and upcoming seasons.

Despite the pressures and the disappointing season trajectory, Hoyer’s position seems secure, largely influenced by Cubs owner Tom Ricketts’ confidence in his leadership, regardless of the mounting challenges. Moving forward, the Cubs’ path remains fraught with difficult decisions as they navigate an increasingly complex MLB landscape.