The Chicago Cubs’ Shopping List: What They Need Before the 2026 MLB Trade Deadline

The Big Picture: Cubs Are Buying, Not Selling

The Chicago Cubs are in "win-now" mode. With the 2026 MLB Trade Deadline arriving on Monday, August 4th, the front office is working the phones to upgrade the roster for a playoff push.

Important Point: Unlike in years past, teams cannot make trades after August 4th. The old "waiver deadline" in August is gone. This means Monday is the final chance to add players for the rest of the season and playoffs.

Why the Bullpen Is a Top Priority

You might hear the Cubs need a starting pitcher first. That’s true. But the bullpen (relief pitchers) is just as critical—and a little scary right now.

The "Injury Bug" Just Bit Again

• Friday news: Reliever Gavin Hollowell went on the Injured List (IL) with right shoulder inflammation.
• He had a 2.51 ERA (very good) in 14⅓ innings.
• Manager Craig Counsell says it’s not serious, but it proves how fast things change.

Help Is Coming… Eventually

Key Risk: Relying on injured players to return and pitch well is a gamble. The Cubs don’t want to gamble.

What Kind of Reliever Are They Hunting?

The Cubs’ bullpen has a 3.94 ERA (solid), but they’re 21st in MLB with a 21.4% strikeout rate. Translation: They get outs, but not enough swing-and-miss outs.

The Wish List: Righties Who Miss Bats

• Preferred: Right-handed relievers
• Must-have: High strikeout ("whiff") rates
• Why? Strikeouts = no balls in play = no errors, no bloop hits, no stress.

Counsell puts it simply:

"Everybody loves strikeouts. The analysts love them, Jed [Hoyer] loves them, the pitchers love them. Hitters don’t. That’s what you want."

But he also adds: Getting outs is the bottom line. They’ll take anyone who does that consistently.

The Current Bullpen Puzzle Pieces

Lefties (Already Set?)

• Caleb Thielbar – High leverage, high K-rate
• Ryan Rolison – Solid lefty, good K-rate
• Hoby Milner – Expected back soon
• Antoine Kelly – Just called up Friday, "wild card" lefty

Righties (Where Help Is Needed)

• Trent Thornton – 3.03 ERA, but only 11.8% K-rate (risky in high-leverage spots)
• Jacob Webb – Above-average K-rate
• Tyler Ferguson – Above-average K-rate (but unproven)
• Caleb Thielbar – (Lefties listed again for emphasis)

Top Trade Targets: The "Dream" Gets

1. Adrian Morejon (San Diego Padres) – The Unicorn

• Lefty throwing 99 mph
• 27% K-rate, 6.3% walk rate (elite)
• Would instantly be Cubs’ best reliever
• Catch: He’s a rental (free agent after 2026), but cost in prospects would be very high. Cubs may not pay it.

2. Luke Weaver (New York Mets) & Jeff Hoffman (Toronto Blue Jays) – The Power Righties

• Both throw hard, miss bats, and are under contract through 2027 at $11M/year.
• Pros: Impact arms, cost control for next year.
• Cons: High prospect price + $11M commitment for a reliever in 2027 = not typical Cubs style.
• Status: Cubs "showing interest" but may balk at cost.

The "Plan B" Tier: Solid, Cheaper, Maybe Less Flashy

If the price is too high for the stars, Cubs could add multiple decent arms instead of one superstar. They did this last year:

• Andrew Kittredge → Exceeded expectations, became key late-inning weapon
• Taylor Rogers → Didn’t work out as hoped

Name to Watch: Antonio Senzatela (Colorado Rockies)

• Righty, first year as full-time reliever → Breakout season
• Not a strikeout artist (Cubs prefer K’s)
• Recent slump: 8.47 ERA in last 17 innings
• Upside: Cheaper cost, team control, ground-ball guy

The Strategy: Prospect Capital Allocation

Front Office Logic:
"We have limited prospects (young talent). Do we spend them on a starter OR a reliever?"

• Priority #1: Starting pitcher
• Priority #2: Bullpen help (likely from "Tier 2" – cheaper, less certain)
• Expectation: Both a starter and a reliever added by Monday night.

Summary: What to Expect by Monday

1. Cubs will add a starting pitcher (top priority).
2. Cubs will add at least one reliever (likely right-handed, ideally high K-rate).
3. They probably won’t pay "superstar prices" for Morejon, Weaver, or Hoffman.
4. Look for a "Kittredge-type" find – undervalued, team likes the data, low cost.
5. Internal help arriving (Palencia, Harvey, Brown, Steele) by mid-August.

FAQ: Your Trade Deadline Questions Answered

Why can’t teams trade after August 4th anymore?

A: MLB eliminated the "waiver trade deadline" a few years ago. Now, July 31st/August 4th is the hard deadline. After that, rosters are frozen for the playoffs.

What does "high-leverage" mean?

A: High-leverage situations are the most critical moments in a game—like bases loaded, 1-run lead, 8th inning. Managers use their best relievers here.

Why are strikeouts so valued for relievers?

A: A strikeout guarantees an out. No fielder can drop it, no bad hop, no bloop single. In high-pressure moments, control = safety.

What is a "rental player"?

A: A player on an expiring contract. They’ll be a free agent after the season. Teams trade for them for a short playoff push, but lose them after.

Why would the Cubs hesitate to pay $11M for a reliever in 2027?

A: Relievers are volatile (performance swings wildly year to year). Committing big money long-term to a non-closer reliever is risky business. The Cubs prefer flexibility.

Stay tuned to The Athletic’s live coverage for every move as the deadline approaches. The next 48 hours could shape the Cubs’ October.