Well, Jed Hoyer Certainly Had a Trade Deadline

Perhaps more than any other team in MLB, the 2026 Chicago Cubs approached the Trade Deadline last Monday with incredible clarity. The position players are elite, producing three more fWAR than the next closest group, the dreaded Dodgers. But the pitching? Yikes! Between injuries -- so, so many injuries -- and some ineffectiveness, Cubs pitchers produced a bottom-five fWAR through July.

And man, those injuries. It has been insane. The Cubs' Injured List pitching staff is undeniably a playoff-caliber collection of talent. For reference, a healthy starter should have thrown 120-130 innings thus far (Shota Imanaga is at 132.2 IP and Colin Rea is at 117.2 IP despite a few relief appearances) whereas a healthy reliever should be at roughly 50 innings (Jacob Webb is at 50.2 IP). Here's the brutal injury story:

Starters

1. Justin Steele (0 IP this year)
2. Cade Horton (7.1 IP this year)
3. Ben Brown (pitched like an ace...but only for 68.0 IP)
4. Matthew Boyd (72.2 IP this year)
5. Edward Caberera (72.1 IP this year)

Relivers

1. Daniel Palencia (16.2 IP this year)
2. Hunter Harvey (4.0 IP this year)
3. Riley Martin (8.1 IP this year)
4. Phil Maton (27.2 IP this year...and they've been terrible)
5. Hoby Milner (35.2 IP this year)
6. Porter Hodge (0 IP this year)

It's tough. Nevertheless, with the team on track to reach the Postseason but severely lacking in playoff-caliber pitching (apologies to David Peterson, who has been plenty solid!), Jed Hoyer had a clear mission: bring in the arms. And bring in the arms he did, acquiring multiple playoff-caliber starters and an ascending reliever to complement the current roster. To be clear, the 2026 Cubs will benefit in a huge way.

So why in the world am I grumpy about this?

Let's say your spouse sends you to the grocery store and says "I need a gallon of organic whole milk." If you go to a corner store, its entirely plausible that there will be one or even zero options, forcing you to pay whatever price is demanded. Don't do that! Thankfully, if you have a Meijer or other similar large retailer available, you can head to that store and find yourself bombarded with quality options. I like to imagine Jed Hoyer holding a crisp $20 bill in his pocket and looking at the milk refrigerator. There are so many options. Option A costs $7, Option B costs $8, Option C costs $6, Option D costs $18, Option E costs $19, and Option F costs $3. Maybe Option D came from the rolling hills of Northern England, Option E offered small-batch milk, and Option F was stomped on a few times so the carton was dented. I don't know. In any event, Jed surveyed the field and must have said, "welp, I can only see Options D and E working for my family." Never mind that Options A, B, and C were all available, absolutely did the job, the store was willing to sell them, and they cost dramatically less. But let's start with Option F.

Hoyer made his best trade in years on Sunday, acquiring playoff starter Kevin Gausman from Toronto for Ty Southisene and Brett Bateman. Gausman arrived alongside his hefty salary -- $23M in 2026 -- so it seems that Hoyer put the Ricketts family money to good use in absorbing this contract. Admittedly, Gausman is 35 and showing some modest signs of slipping from his peak, namely a slight uptick in HR/9 and a slight drop in his fastball velocity from about 94.5 mph down to 93.9 mph. These will be problems for Gausman's agent selling his client on the open market this winter, but 2026 Gausman is largely unaffected, pitching to a tasty 3.50 FIP and amassing 2.6 WAR across 127.1 IP in his age-35 season. He's a playoff starter with a plus fastball and a devastating splitter. With all due respect to Southisene and Bateman, they are horribly flawed prospects with 20-30 grade power such that even their plus speed will likely limit them to bench roles if they mature as hoped. I suspect that Toronto's management required GM Ross Atkins to unload Gausman's money, forcing his hand. Hoyer pounced.

Grade: A

Hoyer next made the same kind of deal, shipping homeless IF Jonathon Long and RHP Jace Beck to Miami for former top-10 pick LHP Braxton Garrett. This transaction is a bit more complicated than the one above, but it follows the same basic approach: trade a flawed prospect who projects as a backup-only player for someone at a desperately-needed spot now. Garrett's 2026 has been a mess coming off of Tommy John surgery in 2024 that also knocked him out for 2025. Despite a rocky climb through the Marlins' system, Garrett was a good Major League pitcher in 2022-23, and it's not crazy to think that he could be so again, either now or in his next two arbitration years. This isn't a marquee acquisition, but it's a great trade.

Grade: A-

And then Jed kept dealing. On Monday afternoon, shortly after acquiring Garrett, Hoyer agreed to acquire RHP Ryan Zeferjahn from the Angels. In a vacuum, acquiring Zeferjahn is good. He's a reliever and the Cubs desperately need more of those. And Zeferjahn does throw really hard with a sweeper that breaks a ton! He even strikes out a ton of batters, checking in at nearly 13 per nine innings this year! Unfortunately, Zeferjahn has a few warts that bear mentioning:

1. He has a subpar pedigree. He was drafted at #107 in 2019 and signed below slot, then peaked at #44 on Boston's prospect list in 2021.
2. Walks. My God. In Zeferjahn's last minor league season (2023), he walked 7.83 per nine. He slowly cut that number, but he still has a dreadful 5.40 BB/9 rate this year.
3. Recent value. Zeferjahn was terrible in 2025, posting -0.6 WAR for the Angels, placing 144th among 147 qualified relievers last year. He surely would've cost peanuts in the offseason.
4. Role. On an Angels team with no dedicated closer (six different Angels have combined for 14 total saves this year), Zeferjahn pitched in the middle innings.

Which brings us to the problem here: the cost. Zeferjahn was Option D among the milks above. He cost $18 and it makes no sense that he did. To get him, Hoyer parted with Moises Ballesteros. Ballesteros has had an underwhelming year, no doubt. He found himself hitting in the cleanup spot in Chicago and he was playing in Iowa by early July. Ballesteros struggled to hit his way on base and to get his plus power to show up in Major League games. But he did all of this in his age-22 season! And just three months ago, he was the club's #1 prospect, ranking #43 in MLB, a few spots ahead of Toronto SS Arjun Nimmala (#49). Had Ballesteros struggled a year at Triple-A, this deal could've made some amount of sense. But he didn't. Ballesteros is $18 of value traded for $5 of value, and that makes absolutely no sense. To make matters worse, Nimmala -- in the midst of an average season at Double-A -- was traded alongside some filler to the Angels for controllable playoff starter Jose Soriano a few hours earlier, someone who was surely a top Cubs target. And it's even worse because the Cubs added sweetener to the deal in the form of Mason McGwire. McGwire is no top prospect; instead, he's Zeferjahn in three years if everything goes right. He's a $1 or $2 throw-in...but why are the Cubs sending the throw-in here? It makes no sense. The only thing that prevents an F grade here is the fact that Zeferjahn is a pitcher and Ballesteros is not.

Grade: D-

And then Jed went even bigger. Ugh. Clay Holmes is a good MLB pitcher. After a strong run of relief pitching for the Yankees from 2021-24, Holmes moved to Queens and the starting rotation and delivered a nice season for the Mets in 2025. But to be clear, "nice" doesn't mean "great" here. Holmes has never had a season of even 2.0 WAR, he's rehabbing a broken leg at the time of this trade, and he's an impending free agent. Even if Holmes comes back this weekend (as hoped) and pitches well for the Cubs, it's impossible for him to produce a ton of value, regardless of role. Tyrone Taylor came alongside Holmes and offers a plus short-side platoon bat in the corner OF. That's nice to have, especially with Ian Happ cratering, but as an impending free agent himself, Taylor surely didn't cost that much. Which brings us to the cost: the Cubs' new #1 prospect and #47 overall SS Jefferson Rojas. A prospect of Rojas's caliber brings back one of two things in a trade: a star or a good controllable piece. Somehow, inexplicably, Rojas brought back neither. It sure seems like Mets POBO David Stearns set a sky-high price and Hoyer blinked.

It is impossible to overstate just how disastrous this trade was. In terms of prospect value, the Cubs could have added Rojas and Ballesteros together to get in the conversation for Tarik Skubal, another impending free agent but also a two-time defending Cy Young winner, not a nice #4 starter or swingman like Holmes. And consider this: at the time of the 2021 trade that sent Javier Baez to New York, Pete Crow-Armstrong ranked #201 overall on Fangraphs and somewhere well outside of the top-100 on MLB.com, behind other Cubs non-elite prospects like Brennen Davis, Cristian Hernandez, James Triantos, Caleb Kilian, and Jordan Wicks. PCA was seen as having an elite glove and a terribly troubling offensive profile that risked scuttling the whole operation. The only concern about Rojas is his ultimate ceiling. Will he get to enough power and show enough range to be an All-Star, or will his slight limitations render him only an average starter on the dirt? Regardless of the answer, he's an immensely valuable prospect with a dramatically higher floor than most players traded at the deadline, he's a consensus top-100 prospect, and most folks see him among the top 50 prospects in baseball.

Even with an important arm coming back in the form of Holmes, this is such a drastic overpay that it's impossible not to fail.

A final note: I've seen lots of commentary about how Rojas won't have a role in Chicago because of the significant contracts held by Alex Bregman, Dansby Swanson, and Nico Hoerner. To which I say this: hogwash. Rojas could cook for all of 2027 and look to make the Majors in 2028, at which point Swanson will be 34 with only two years left on his deal, Hoerner will admittedly be 31 with five years left on his disastrous extension, and Bregman will be 34 with three years left on his deal. It's entirely foreseeable that Swanson or Bregman (or *gasp* both) will have slowed down considerably by 2028, requiring a new SS to carry the mantle or to spell them a few times a week at the very least. And Pedro Ramirez had no path to the roster this year, yet he already has 117 PAs on his way to something in the neighborhood of 250 PAs. Playing time opens up for good players.

When the 2015 Cubs had Rizzo-Baez-Russell-Bryant across the infield, they didn't tell Ben Zobrist to pound sand because they were all set; they added another awesome player to the mix and it made all the difference en route to a championship. Apologies to Tommy La Stella.

The farm system is now completely barren on the dirt, particularly on the left side. Ramirez is a 2B-only glove. James Triantos is a fringe MLB player and 2B-only with the glove, too. After them, Josiah Hartshorn is the only other top-20 organizational prospect who projects to play on the infield, and even Hartshorn is already limited to 1B in A-ball.

The Cubs had a bevy of outfielders from which to deal, led especially by Kane Kepley and Kevin Alcantara. Surely some sellers would have been interested in those two, perhaps even the Tigers, who also shipped out rental Casey Mize for a relatively middling package headlined by San Diego LHP Kash Mayfield. That kind of price would've been appropriate for a rental.

Rojas for Holmes and Taylor? Not so much.

Grade: F

Hoyer's trade history during his time atop the Cubs' organization was already poor before this deadline. The Gausman deal suggested that he was on a different path and the Garrett deal was a shrewd follow-up. But then it all fell to pieces and culminated in his new worst move as POBO. Brutal.