3 Mock Trades That Would Make for a Perfect Cubs Deadline

The Chicago Cubs have as clear a plan as anyone as they head into the 2026 trade deadline. They have dealt with pitching injuries to both their rotation and bullpen since the beginning of the year. That leaves them to target one thing in specific: pitching, pitching, and more pitching.

There are going to be plenty of arms available at the deadline, both starters and relievers. As with every deadline, struggling teams may look to sell off major-league talent and bolster their farm systems to build for the future.

Thanks to multiple breakout prospects in the Cubs organization, they have the capital to acquire some impact pieces at the deadline. It is a similar approach as last season for them, though after they took a cheaper route that failed, they may look to get more aggressive this season.

With the addition of at least one starter and one leverage reliever, Jed Hoyer’s squad will be in much better shape. They currently hold the top wild-card spot in the National League, but reinforcements are important to a deep run in October.

Without further ado, let’s look at three trades that could make for a great Cubs deadline.

Trade One: Cubs Acquire High-Leverage Reliever From the Mets

Cubs Get: RHP Luke Weaver

Luke Weaver has been one of the most dominant relievers in baseball this season and would immediately become Craig Counsell’s top late-inning option. With the current state of the Cubs’ bullpen dealing with a nearly unfathomable number of injuries, adding a proven leverage arm would be massive down the stretch.

He has racked up strikeouts at a 26.4% rate this season, well-above league average and something the Chicago bullpen has generally lacked. He ranks in the 78th and 81st percentile in chase and whiff rates, respectively, while also limiting hard contact at an impressive level.

These successes have fueled his production this season. Over 42 innings pitched, he’s posted a 1.93 ERA with a 0.83 WHIP that ranks 10th lowest among qualified relievers.

Weaver hasn’t had many save opportunities this season, as the Mets have given that role to Devin Williams, but does have experience closing games.

In the 2024 playoffs, he recorded four saves and had eight of them during the regular season in 2025. He’s not entirely unfamiliar with a postseason atmosphere, playing in 15 playoff games over the last two years, posting a 4.60 ERA in those outings.

Among relief pitchers set to become available at the deadline, Weaver might be the Cubs’ best option. The price may be high for a bullpen arm, but with the production and extra year of control, Jed Hoyer will have to pay up.

Mets Get: C Owen Ayers, RHP Kaleb Wing

A return of Owen Ayers and Kaleb Wing would be an interesting one for the Mets.

Beginning with Ayers, he’s a 25-year-old catching prospect in the midst of a breakout season in 2026. Since slashing .379/.539/.591 and taking home the Breakout Player of the Year Award in the 2025 Arizona Fall League, he has not stopped hitting.

He began his 2026 campaign in High-A, though he didn’t stay there long. After slugging six home runs and posting a 1.341 OPS over 11 games, he was moved up to Double-A Knoxville.

That remained his home for the next couple of months, where he continued to terrorize opposing pitchers, running a 1.009 OPS over a 65-game span. That was enough to earn him a promotion to Triple-A, where he is batting nearly .400 across his first 28 at-bats.

Though he’s on the older side for a prospect, he’s shown ability to adjust at multiple levels. Ayers is not an untouchable by any means, but he would warrant a solid return.

As for Kaleb Wing, he’s on the far other spectrum in terms of prospect age. At just 19 years old, he’s shown some promising stuff.

He has a fastball that will work around 94 mph, generating roughly 19 inches of induced vertical break (IVB) in the process. To go with it, he’s got a changeup that runs heavy to the arm side and misses bats, with a pair of breaking pitches that have flashed plus potential.

The look at him has been limited, as he’s been down with an injury since June 25. Still, in six starts with Single-A Myrtle Beach, he showcased elite strikeout ability. However, that did not come without some command issues.

For Chicago, this is the type of aggressive move contenders have to consider. Weaver immediately strengthens the club’s biggest weakness while the Mets acquire two intriguing long-term pieces to aid their future.

Trade Two: Jed Hoyer Gets His Controllable Starter

Cubs Get: LHP Reid Detmers

Dating back to last year’s trade deadline, the Cubs have constantly been involved in conversations for young, controllable starting pitchers. They finally made good on that need this winter, trading for Edward Cabrera from the Marlins. However, that deal has not yet paid off, with Cabrera both struggling to succeed and stay healthy.

Trading for Reid Detmers could allow for redemption of sorts. After relieving in 2025, Detmers has once again been stretched out as a starter and is seeing solid results. Over 21 starts and 120 innings this season, he has a 4.05 ERA and 136 strikeouts.

At face value, the ERA may seem underwhelming, but according to expected stats and FIP, he is due for some better luck. Among pitchers with at least 100 innings pitched this year, he ranks top 15 in both FIP and xERA, both marks at 3.32 or lower.

Detmers can also provide some much-needed swing-and-miss to the Cubs’ rotation. He’s worked a 27.6% strikeout rate and 28.6% whiff rate this season. While he doesn’t come without some issues in suppressing hard contact, he would still make a huge impact for the Cubs.

Detmers would remain under team control through the 2028 season, giving Chicago a chance to add not only for this postseason but for multiple years beyond. The only caveat would be the price, which is understandably very high.

Angels Get: INF Pedro Ramirez, RHP Jaxon Wiggins, OF Kane Kepley

A package of Pedro Ramírez, Jaxon Wiggins, and Kane Kepley is a haul.

The first of the three is Ramírez, who has already graduated from prospect status. A versatile utility player, he had long been a respected name in the Cubs’ system before breaking out in 2026. Although he’s received inconsistent playing time over the past couple of months, he’s continued to produce when given the opportunity with Chicago.

Over 90 big-league plate appearances, he’s slashing .305/.348/.451, good for a 120 wRC+. He also plays steady defense, mostly at second and third base, though he’s played corner outfield a bit in the minor leagues.

There’s a lot to like about his game. He makes consistent contact, his power continues to improve, he’s a threat on the basepaths, and he can hit from both sides of the plate.

Perhaps the highest ceiling of these three is the Cubs’ current top pitching prospect, Jaxon Wiggins. In 2025, he dominated the minor leagues across three levels. A 2.19 ERA and 97 strikeouts over 78 innings got fans excited to see what he could turn into.

That excitement has been put on hold this season due to an early injury that he just returned from. There hasn’t been much time for him to find his footing this season, leading to less-than-impressive results. Looking past that, he features elite level stuff.

His fastball will run in the upper-90s and graded out as one of the best in the minor leagues. The wipeout pitch in his arsenal is a hard slider, which consistently misses bats and has mostly induced weak contact this season. A pairing of a curveball and changeup will also be mixed in at lower rates.

Wiggins does struggle with command, which leaves his future as a starter in question. Still, his ceiling is high whether he ultimately sticks in the rotation or moves to the bullpen.

Rounding out the deal is Kane Kepley, an electric prospect. He is a player who knows his game as well as anybody. Rather than trying to hit for power, he prioritizes reaching base. His 20.7% walk rate and 1.45 BB/K are both top 10 in the minor league among hitters with at least 300 at-bats.

After reaching base, he becomes more of a threat. Through 87 games this year, he’s swiped 47 bases while being caught just five times. As you may have guessed, Kepley is fast, which he also uses to power elite defense.

Each of these prospects is exciting in his own way and could play a significant role in the Angels’ future. At the same time, it wouldn’t be easy for Cubs fans to see them go, but acquiring impact talent often requires parting with promising young players.

Trade Three: Cubs Add Another Veteran To the Rotation

Cubs Get: RHP Kevin Gausman

Making a move to acquire Kevin Gausman may not be the big move Cubs fans are looking for, but it would still be an impact play. The biggest factor in his game is one the Cubs desperately need: health.

In each of the five seasons prior to this year, he pitched at least 170 innings. He has done so while also consistently finding success. It was not until this season that he saw a jump in earned run average. The ERA does sit at 4.51, though he has a 3.58 FIP with solid peripherals.

In the quality of contact department, he has been hovering right around league average. At times, he can be more susceptible to damage even though he’s decent at limiting hard contact due to his low ground ball rates. With the Cubs’ elite defensive outfield, however, some of that could be eliminated.

To go along with this, he’s sitting in the 57th percentile in strikeout rate while also inducing chase and whiffs at a high rate.

Unlike some other Cubs targets, Gausman has postseason experience, and a good amount of it. In his career he’s tossed 56.1 innings in the playoffs, working a 3.83 ERA during those outings. This makes him more enticing for a contending team.

When it comes to the price, he is a 35-year-old rental who is having somewhat of a down year. The return likely won’t be anything crazy, but that could open the door to make multiple impact moves.

Blue Jays Get: RHP Brooks Caple, SS Juan Cabada

Headlining this package is 23-year-old pitching prospect Brooks Caple. He’s a guy who burst onto the scene in 2026, flashing strikeout stuff and great production.

His season began at High-A before he earned a promotion after just five starts. He’s found success at both levels, posting a 3.26 ERA across 77.1 innings. What has the organization especially excited, however, is his significant improvement in both strikeouts and command. That progress is reflected in his K-BB%, which has jumped 12.7 percentage points from last season.

With his sustained success at Double-A, a promotion to Triple-A may not be far away. A pitcher who could be knocking on the door of the majors in the near future would be an exciting addition to Toronto’s long-term outlook.

In addition to Caple, Juan Cabada is another solid prospect. As with any young international prospect, he is a lottery ticket, though he’s shown ability to hit since signing with the Cubs organization.

Currently, he’s in the Arizona Complex league, where he’s batting .283 over 14 games this season. There isn’t a ton of power in his bat, but at 18 years old, he’s still developing physically and will likely improve in that department in the coming years.

Last season in the Dominican Summer League, he swiped 20 bases in 42 games, so there’s certainly some athleticism in there. Some scouts believe he could become a similar player to Pedro Ramírez with the potential to have more power.

For the Cubs, Gausman would be a solid addition on his own, but pairing him with another starter or a legitimate high-leverage reliever at the deadline would make for a huge win. They wouldn’t have to empty the farm system to acquire him, yet they’d still add an experienced, impactful arm.

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Closing Thoughts

The Cubs are in an excellent position to improve at this year’s trade deadline. They have the prospect capital to land impact players, and the market should provide plenty of opportunities to do so. The question isn’t whether they can make meaningful additions, but whether they’re willing to pay the price to maximize their World Series chances.

Chicago already has one of the National League’s most talented lineups. If the club can reinforce its pitching staff, it has all the pieces needed to make a deep postseason run. With several injured pitchers expected to return, a few deadline additions could elevate the Cubs into the conversation as one of the World Series favorites.

Windows to compete for a championship don’t stay open forever. Jed Hoyer has a chance to capitalize on one of the best teams he’s assembled in Chicago, and an aggressive deadline approach could be the move that defines the Cubs’ season.