Analyzing the New-Look Chicago Cubs After the 2026 Trade Deadline

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Well, that was fun. What an insane, fast-paced, chaotic trade deadline 2026 delivered. As many observed during the heat and smoke of it, the day felt virtually the opposite of the way the 2025 deadline did. That day, though the Cubs technically made a couple of fine moves, no one was blown away. No one was even especially moved. This year, when the dust settled, the Chicago Cubs came away with five new players: Clay Holmes, Ryan Zeferjahn, Braxton Garrett, Kevin Gausman and Tyrone Taylor.

With the additions will come roster moves that must eventually be made, and roles will be shifted up and down the roster for the remainder of the season. Let's dive into what will change for the final two months of the season, and what it all means for the team's chances.

Starting Rotation
Let's start with the rotation. Three starting pitchers were added, but it will only be Gausman and Holmes who go straight into the starting rotation. Garrett has pitched to a 14.54 ERA in 4 1/3 innings in the majors this season and was working at the Marlins' Triple-A affiliate; he'll start at Iowa and get a chance to work with Cubs coaches outside the limelight.

Along with incoming roster moves for Gausman and Holmes, the Cubs could also soon be getting Edward Cabrera back. Holmes has made three rehab starts already in his return from a broken leg, throwing 51 pitches on July 23; 59 on July 28; and 73 on August 2. He'll meet with the team before deciding on the next steps, but it's likely that he'll be ready for reinstatement and to pitch in the majors at the end of this week. Gausman is tabbed to start Thursday against the Blue Jays (his former team), when Toronto is likely to send Jameson Taillon to the bump at Wrigley Field against the Cubs (his former team). Cabrera, meanwhile, threw 43 pitches in his first rehab start after a major muscle strain suffered back in late June; he's likely to come back closer to the end of this month. As each hurler joins the squad, who will be pushed into a new role, or off the roster altogether?

The most likely scenario would be Javier Assad being optioned back to Triple-A. That would be a bitter pill for Assad to swallow, as he's consistently proved he's a capable starter at the big-league level and has generally answered admirably when his number has been called. Unfortunately, though, after he makes his scheduled start on Tuesday, Assad will not have a path to stay in the rotation or the bullpen, barring further attrition somewhere in the pitching staff. By the beginning of next week, the rotation should include Gausman, Shota Imanaga, Matthew Boyd, David Peterson, and Holmes.

Bullpen
Zeferjahn was the only bullpen move made, meaning the decisions there will be a bit easier. When Holmes joins the rotation, though, Rea will slide from the rotation to the bullpen, so the team needs to create two new openings.

Jacob Webb, Caleb Thielbar, Zeferjahn, Ryan Rolison and Rea have safe places on the depth chart. Everyone else's place is in peril for a while. Trent Thornton will probably survive the first round of cuts, because he's not optionable. Neither are Aaron Civale or Jake Woodford, but those two came to the Cubs as flotsam and could rapidly become jetsam. However, since Antoine Kelly and Tyler Ferguson are both optionable, they might be bumped to Iowa rather than lose any member of the team from the organization.

The roster decisions will get tricky when everyone is healthy and ready to come back. Some tough decisions will ultimately have to be made, especially upon the relatively imminent returns of Daniel Palencia and Hoby Milner. More pitchers might hit the injured list, but the team now has so much starting and relief depth that they could face a roster crunch at some point in the latter part of August.

Lineup
Taylor was the lone bat the Cubs added at the deadline, and Monday's lineup may give a clear indication of what his role will be. Chicago was up against left-hander Justin Wrobleski, and it was the freshly-recalled Kevin Alcántara who got the start in left field over Ian Happ. Alcántara is in his final year of eligiblity to be optioned, and since he wasn't traded, the Cubs now need to get a meaningful look at him in the majors before the offseason.

Taylor's playing time might be sparse, especially once the team finishes cycling through days off for each regular amid a long stretch between off days on the schedule. Alcántara will have to get some reps, and the Cubs affirmed their commitment to do that by calling him up at the expense of Justin Dean. Taylor, then, will take on Dean's vacated role, filling in as a backup across the outfield and spelling any of several Cubs hitters against left-handed pitchers. That's a good gig for him; his slash line of .301/.311/.589 against lefties is worlds better than Happ's line of .158/.232/.298.

We could immediately see James Triantos sent back to Iowa. Unlike Alcántara, Triantos can still be optioned to the minors next season, and more importantly, it's not clear that Triantos is needed. With Pedro Ramírez around to back up multiple infield positions, the team can option Triantos and use Alcántara, Taylor and Michael Conforto to play matchups at designated hitter and in the outfield.

Matt Shaw is making material progress toward a return from his second injury of the year. Eventually, he might return, too, forcing Alcántara (or Triantos, if he's the one kept up after Taylor's arrival) back to Iowa. In any case, though Taylor gives the team more depth and more danger against left-handed pitchers, as well as another athlete in the outfield.

Two days ago, the Cubs were desperate for better depth. They're now a much, much deeper club, ready to challenge for a deep run in the postseason. The roster is bursting at the seams. Injuries will erode that excess quickly, but for now, the team can luxuriate a bit in its newfound multitude of options.