Cubs’ Trade Deadline Strategy Remains Uncertain

Cubs president of baseball operations Jed Hoyer stated on Friday that the next two weeks will be critical in determining the team’s strategy for the upcoming trade deadline on August 3. The situation remains unclear as uncertainty over which teams will sell persists. Hoyer emphasized the importance of waiting, noting a ‘jumble’ of teams in contention, especially in the American League.

Referencing past experiences, such as the 2023 season, highlights the unpredictability of the trade deadline. The Cubs appeared out of the race at five games below .500 at the All-Star break but surged back with a winning streak, nearly capturing a wild-card spot. This taught the Cubs to not make premature decisions as the deadline approached.

Entering Friday night, the Cubs held the top wild-card spot and trailed the Milwaukee Brewers in the NL Central by five games, positioning them as potential buyers. “We’ve put ourselves in a good position,” Hoyer said, focusing on improving the pitching staff but remaining open to other possibilities.

One key sign of hope is the anticipated return of starter Jameson Taillon next week, following his recovery from a hamstring injury in early June. Cubs manager Craig Counsell announced that Taillon would rejoin the team for the series against the Detroit Tigers, although the exact game he will pitch is yet to be decided.

Progress in other pitcher recoveries offers promise. Right-handed starter Edward Cabrera aims to return by the second week of August after a left hamstring/adductor strain. Lefty reliever Hoby Milner is nearly healed from an appendectomy, targeting an early-August return. Closer Daniel Palencia’s return is expected by mid-August, slightly later than initially planned due to setbacks.

Starter Justin Steele, absent from play since April 2025 due to a flexor strain, may begin bullpen sessions soon, although his long absence necessitates a gradual ramp-up process. Third baseman Matt Shaw remains sidelined with a lingering wrist sprain.

Hoyer stressed that irrespective of returning players, the Cubs will prioritize acquiring additional pitching via trade, revealing a consistent approach despite challenges. “I’ve said a million times, you can never have too much pitching,” Hoyer remarked, emphasizing the importance of depth and resilience amidst an injury-riddled first half.