Key Points
Bullet point summary by AI
- The Chicago Cubs and Pittsburgh Pirates share urgent needs for pitching upgrades ahead of the trade deadline, but their financial approaches differ sharply.
- Pittsburgh's payroll history and current spending limits prevent them from pursuing high-cost rentals or arbitration-eligible arms.
- Chicago's deeper pockets allow them to target high-impact pitchers who could reshape their playoff rotation and bullpen by August 3.
The Chicago Cubs and Pittsburgh Pirates collide this weekend at PNC Park in pretty similar situations. Chicago won the series opener on Friday night and leads their division rival by 5.5 games in the standings, but both teams have shown enough to feel good about their Wild Card chances — and have earned the right to be buyers ahead of the trade deadline. Their deadline wish lists, too, are virtually identical: pitching, pitching and more pitching, in both the rotation and the bullpen.
There's one very important difference between the two, though: the money they have to spend. The Cubs are one of the richest teams in the sport, while the Pirates have never finished a season with a payroll over $100 million (they currently sit around $106 million, per Spotrac). So while Pittsburgh and Chicago should be fighting to solve the same problems between now and Aug. 3, only one of them can take on significant money to do so — which means there's a whole class of trade candidate the Pirates probably won't have access to.
The relievers
RHP Mason Miller, San Diego Padres
Let's start with the biggest fish of all, as rumors continue to swirl around the possibility of the San Diego Padres trading their star closer. And to be sure, both of these bullpens have been leaking oil of late and could really use a pitcher of Miller's caliber. (Heck, every contender could use a pitcher of Miller's caliber.)
From Pittsburgh's perspective, though, there's just one problem. Miller is about to hit arbitration for the first time next season, and while that process is always difficult to predict, it'll likely result in a major pay bump for the guy who is in a class of his own among relievers. Are the Pirates prepared to be on the hook for that money, never mind the subsequent raises coming in 2028 and 2029 before hits free agency? History suggests no.
RHP Luke Weaver, New York Mets
Weaver has been one of the few bright spots amid a lost season for the Mets, pitching to a sub-2.00 ERA so far. A Pirates team desperate for more righty relief options could hardly do better, especially if Miller is staying put (or the price is simply astronomical). In addition to the rest of his 2026 salary, though, he's due $12.5 million in 2027, which is just about more than Pittsburgh has ever spent on a single reliever. He'd make all the sense in the world for the Cubs, though, with both Daniel Palencia and Phil Maton both currently on the IL.
RHP Jeff Hoffman, Toronto Blue Jays
On first blush, Hoffman wouldn't seem all that appealing to would-be contenders given his 4.30 ERA and 1.43 WHIP (and the fact that Blue Jays fans would love to run him out of town on a rail). So much of his struggles in 2026 seem to be the result of bad luck, though: His chase, whiff and K rates — you know, the stuff a pitcher has direct control over — are all off the charts. Plenty of bullpens could use a guy who misses bats as well as almost any reliever in baseball, trusting that the batted-ball outcomes will normalize in time.
Hoffman is due $12.67 million next season, though, which again would seem to put him outside of Pittsburgh's price range. The Cubs should absolutely be calling Toronto to see how desperate they are to get out from under his contract.
The starters
RHP Joe Ryan, Minnesota Twins
The rotation is a more pressing need for Chicago than Pittsburgh, though the Pirates could also use some more rotation certainty given the ups and downs that Braxton Ashcraft, Mitch Keller and Bubba Chandler have endured this season (and the likely innings limit that Jared Jones is working with as he comes back from elbow surgery). Joe Ryan might be the top option available if the Tigers keep Tarik Skubal, but he should also command a hefty salary next year in what will be his final year of arbitration before hitting free agency.
Are the Pirates willing to take that big a swing financially, given all the young pitching they already have? It seems doubtful based on recent history. If he lands with the Cubs, though, he could be transformative alongside Shota Imanaga and Matthew Boyd if Edward Cabrera and Ben Brown can both get back healthy.
RHP Kevin Gausman, Toronto Blue Jays
A free agent at the end of the season, Gausman wouldn't involve taking on any money beyond 2026. But he's still due some $7-8 million from now until the end of the season, and based on the parameters we laid out above, it'll be tough for Ben Cherington to make the money math work in Pittsburgh.
He's struggled a bit in his contract year, but the fastball/splitter combination still looks pretty good under the hood, and he has a ton of big-game experience to fall back on. He's no longer a frontline guy, but if you need someone to start Game 3 of a playoff series — and, if you're the Cubs and you want to maintain flexibility in 2027 and beyond — you could certainly do worse.
LHP Robbie Ray, San Francisco Giants
Ray is in the same boat as Gausman, a veteran rental whose best days are behind him and who is owed significant money at the end of a hefty contract. His topline numbers are much shinier, but that has to do with his pitcher-friendly home park and batted-ball luck more than anything; the lefty has adapted to a kitchen-sink arsenal that allows him to grind his way through starts and keep his team in games. Add in his viability as a lefty specialist out of the 'pen, and he can be a very valuable piece — that is, if you can eat the $7-8 million he's owed for the rest of this season. The Cubs certainly can. The Pirates? That remains to be seen.
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