Chicago Cubs’ Trade Deadline Strategy for 2026

The approach of the August 3 trade deadline leaves questions for the Chicago Cubs. The team’s president of baseball operations, Jed Hoyer, recently discussed the potential paths the Cubs could take. The focus for the coming weeks will be observing shifts within the league to determine the most strategic moves for the team at the deadline.

Many teams in the American League remain in playoff contention, which adds complexity to decision-making. Hoyer highlighted 2023 as a learning experience, where the Cubs, despite initial struggles, turned their season around by holding onto key players like Cody Bellinger and acquiring third baseman Jeimer Candelario.

With the Cubs entering the weekend holding a top wild-card spot and trailing the Milwaukee Brewers by five games in the NL Central, there’s a possibility of strengthening their pitching staff. Hoyer noted that recent and upcoming player developments will play a role in these decisions, especially among injured pitchers.

Jameson Taillon, a starter recovering from a hamstring injury, is expected to return next week, potentially during a series against the Detroit Tigers. This return is promising given the injuries that have previously weakened the Cubs’ rotation.

Edward Cabrera, another starter, is progressing from a left hamstring/adductor strain and aims for an early August comeback. Similarly, lefty reliever Hoby Milner anticipates a return following recovery from an appendectomy.

Closer Daniel Palencia continues his rehab process and targets a mid-August return. The original timeline was early August, but setbacks have delayed his progress. For Justin Steele, sidelined since April 2025 with a flexor strain, bullpen sessions may resume this week, but his long absence requires a cautious return schedule.

The team’s considerations at the trade deadline will not solely rely on potential returns from the injured list. Hoyer emphasized the ongoing need for pitching, stating that a surplus of arms remains unlikely for the Cubs. Injuries throughout the first half of the season have underscored this necessity.

As Hoyer remarked, “you can never have too much pitching and you never have enough,” indicating the Cubs’ intention to remain active in addressing their pitching needs as the trade deadline approaches.