The Cubs don’t need a deadline splash for the sake of optics. They need a plan that works now and doesn’t leave the cupboard bare later, and that’s where the front office’s internal tug-of-war matters.
Jed Hoyer has long been the face of the organization’s careful approach, but Carter Hawkins may be the bigger driver behind the caution. After last summer, Hawkins at least sounds comfortable saying the quiet part out loud.
The Cubs’ front office has generally tried to find value in every move, with the exception of the Alex Bregman signing and the Kyle Tucker trade. Most of the time, Hoyer and Hawkins have wanted deals that improve the team in the moment without damaging what comes next.
In those cases, Hoyer has likely been the one pushing things over the line while Hawkins has been the one flagging the future risk.
That same balancing act is now staring them down at the trade deadline.
The Cubs have had stretches this season where the offense has looked uneven, but there’s also hope that a healthier pitching staff in September could set them up for a real October push. Even so, the gap between the Cubs and the Dodgers is still obvious.
So the front office can’t afford to stand still on the mound. Adding a starting pitcher who can help this season should be the minimum.
That’s why the Tarik Skubal dream is still alive, and why the Cubs are considered a strong suitor for Freddy Peralta. On the rental market, Tyler Mahle has also been linked to them.
At the very least, the rotation should have a new arm by the end of the day on Monday.
But that may not be enough.
North Side Baseball’s Matthew Trueblood reported that the Cubs are also looking at several controllable pitchers who may need some tweaking. Those names would not be immediate fixes for this season, but they could matter for the rotation beyond 2026. That points to the kind of deadline strategy that fits both Hoyer and Hawkins: one move for the present, another with an eye on 2027 and beyond.
Outside of Skubal or someone from the group of Reid Detmers, Jose Soriano, or Emmerson Hancock, the Cubs may need to add two starters. One would be a rental built to steady the rotation for a run in October.
The other would be a controllable pitcher who can become part of the answer down the road. In the end, that may be the cleanest way to satisfy both the measured aggressiveness Hoyer prefers and the caution Hawkins has built his reputation on.
In Other News...
Cubs Just Got Pulled Into Torontos Deadline Rotation Shakeup
Torontos deadline-day rotation shuffle has already sent ripple effects through the league, and the Cubs were pulled into the middle of it before the dust could settle. The Blue Jays moved quickly ahead of the Aug. 3 deadline, adding Jose Soriano from the Angels while also reshaping the staff with veteran arms, a sign they were prioritizing immediate stability as they mapped out the rest of 2026 and even looked ahead to 2027.
For Chicago, the bigger story is how this kind of deal changes the market around it. A club in deadline mode can turn one trade into a broader reset, and the Cubs now sit in the orbit of a Blue Jays rotation plan that could still keep evolving as Toronto weighs future moves involving its veteran pitchers. Even after the first wave of action, the way Toronto sorts out its staff may decide whether this becomes a one-off adjustment or the start of something bigger. [Read more 🡒]
Cubs Just Paid A Real Prospect Price For An October Push
The Cubs made a clear win-now move, parting with one of their better infield prospects to shore up the roster for the stretch run. Jefferson Rojas was sent to the Mets in a deal that brought back Clay Holmes and Tyrone Taylor, a transaction that signals Chicago is treating October as more than a distant goal and more like a window worth pushing through right now.
Holmes gives the Cubs a right-handed arm who is still on the injured list but getting close to a return, while Taylor adds experienced outfield depth for the final months of the season. It is the kind of trade that usually comes with an uncomfortable cost, and Chicago paid it by moving a player it had reason to value, betting the short-term upgrade will matter more than the long-term regret. [Read more 🡒]
Cubs Just Got A Surprising Deadline Opening They Still Needed
The Cubs still have not made a trade move, but they do have one of the more intriguing deadline paths to monitor as they poke around with Texas. The Rangers have shifted their approach enough to at least listen on some pitching, which has put Chicago in the mix for arms such as Nathan Eovaldi, MacKenzie Gore and Jacob Latz. For a club looking for help without blowing up its deadline, that kind of opening is worth watching closely.
Texas, though, has also sent a mixed message to rival front offices, which is part of what makes this whole thing feel so unsettled. Trade talks can turn quickly at this time of year, and the Cubs are weighing options in a market where the other side may not be nearly as available as it first seemed. [Read more 🡒]