The Chicago Cubs approach August with the second-best record in MLB, only a game behind the first-place Milwaukee Brewers in the rough-and-tumble NL Central. This is Jed Hoyer's moment — his chance to turn a strong farm system into a productive trade deadline with a clear path to the World Series in sight. It helps that Kyle Tucker's expiring contract serves as the ultimate ticking time bomb.
How aggressive the Cubs will actually be over the next couple days remains to be seen, but there is plenty of reporting to connect big-ticket names, such as Eugenio Suárez and Dylan Cease, to the North Side. The Cubs are a lucrative organization in a lush financial market. The idea that Hoyer can't spend has always been a bit silly. It is traditionally more of an unwillingness to spend, either on his part or ownership's part.
The Cubs have several needs at the deadline — another dependable rotation arm, bullpen depth, a third baseman — but there's a good chance Hoyer thinks outside the box. We've seen him flip controllable talent for major upgrades in the past, or even just to reshuffle the deck. For examples, look no further than Christopher Morel and Isaac Paredes. Never put it past Hoyer to get a bit weird.
Here are a few Cubs players on the chopping block that you might not expect.
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3. RHP Ryan Pressly
The Cubs inked Ryan Pressly to a one-year, $14 million contract this past offseason. He was meant to address their dire late-relief needs after the failed Héctor Neris experiment in 2024. Well, as it turns out the 36-year-old Pressly is not what he once was. The talented righty has turned things around somewhat are a brutal start to the campaign, but he's no longer dependable in high-leverage situations.
As such, the Cubs might explore moving him, even as Hoyer scours the market for additional bullpen weapons. Pressly has a -0.2 fWAR so far this season, among the worst on Chicago's pitching staff, but his ERA is down to 3.79 and he's something of a name brand. A contender looking for depth pieces with no strings attached could easily talk itself into Pressly as a cheap addition with upside if he can achieve pre-Cubs form. It's only a half-season rental if things go south and he won't cost much of anything in terms of prospect capital.
If the Cubs can get a semi-intriguing top-30 prospect and get off of Pressly's money, thus freeing up more to spend elsewhere, that feels like a win-win. Pressly would surely welcome a new situation with less pressure. His 1.49 WHIP and incredibly low strikeout rate (26 K's in 40.1 innings) are troubling, but just last season Pressly was producing a whiff rate in the 98th percentile. Someone will bite.
2. RHP Ben Brown
Ben Brown is only 25 years old and still in the pre-arbitration stage of his contract, so there is untapped potential and years of team control left. That makes a trade unlikely, but not impossible, especially given Hoyer's track record. The Cubs are looking for immediate upgrades to the rotation. With Javier Assad and Jameson Taillon both close to a return from IL, Brown feels like the odd man out.
Chicago can justify moving Brown to the bullpen for now or even demoting him to Triple-A, but there will be teams interested in adding an arm with upside and control all the way through 2029. Brown holds at a 6.22 ERA and 1.48 WHIP across 18 MLB appearances (15 starts) this season, notching 99 strikeouts in 88.1 innings. His swing-and-miss stuff will pique the interest of contenders, who might view Brown as valuable back-end rotation depth or even as a short-term bullpen upgrade with long-term starting potential. Brown will also appeal to rebuilding teams looking for controllable pitchers. Hoyer can cast a wide net.
Trading Brown is not a necessity, but if Chicago can turn him and a couple more prospects into a bonafide star on the mound (or in the field, preferably at third base), it's worth thinking about. It's impossible to know Brown's future development, but he's in the absolute bottom percentile for exit velocity, which means he's allowing a metric ton of hard contact. He only has two real pitches, too, which makes him a little predictable. There's a lot that needs to change before Brown is the week-in, week-out ace Cubs fans once envisioned.
1. OF Owen Caissie
Owen Caissie is Chicago's No. 1 prospect and No. 36 overall at MLB Pipeline. Rarely are top prospects like Caissie moved at the deadline, but the Cubs are in a particularly desperate spot with all the uncertainty shrouding Kyle Tucker's future. There is enough speculative trade buzz tying Caissie to trades for Suárez, Cease and other stars that it at least merits consideration.
There will be many intense bidding wars over the next few days. Caissie is Chicago's golden ticket — the Cubs' most surefire way to leapfrog the competition and outbid the vast majority of contenders. He's 23, but Caissie is nearing his MLB debut. He offers major power and negates a lofty strikeout rate with a high average and a high walk rate. Pitchers regularly pitch around him with Triple-A Iowa out of fear.
Caissie alone might get Chicago into the mix for the very best players in the trade market. Moreover, the Cubs need to look a few years down the road. If Tucker does stick around, there are limited reps in an outfield that also features Pete Crow-Armstrong and Ian Happ. The Cubs aren't needy at Caissie's position and could be better off translating his immense upside into a star-powered helper right now.