The Chicago Cubs need pitching, and Mitch Keller might be the best starting pitcher available when the trade deadline rolls around. For that, it isn't surprising that the Cubs have been linked ad nauseam to the Pittsburgh Pirates' right-hander. Jon Heyman was the latest to do so for the NY Post ($).
"Ultimately, the Marlins may have the best starters with Sandy Alcantara and the hot Edward Cabrera (1.46 ERA over seven starts). Or maybe it’s the red-hot Pirates, who’ll listen on Mitch Keller. The Cubs have been connected to Alcantara and Keller," Heyman wrote.
While Keller would be a perfect fit for Chicago's rotation, they could use bullpen help as well. That's where David Bednar comes in.
The Cubs' bullpen has been good, particularly lately, but how trustworthy is this unit come October? Daniel Palencia has settled in as the team's closer, but it's not as if he has a long track record of MLB success. Brad Keller has been solid all year long, but it wasn't too long ago that Keller signed a minor leaague deal with Chicago. Guys they expected to be their best relievers, Ryan Pressly and Porter Hodge, have had their ups and downs.
This bullpen has performed well, but it certainly feels as if it could use another arm. Similarly to Keller, Bednar figures to be among the best arms available. The Cubs should be trying to get them both.
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Cubs would win the trade deadline by acquiring Mitch Keller and David Bednar
Keller's track record speaks for itself. He might not be an ace, but he's made at least 29 starts in each of the last three seasons, and he has a 3.61 ERA in 18 appearances in 2025. He's been consistent and durable throughout his career, and he's under contract through the 2028 season on very team-friendly terms. He'd fit in nicely, slotted behind Shota Imanaga in the Cubs' rotation.
What'd make a Keller deal would be if the Cubs could also get David Bednar. It felt as if Bednar was on the verge of getting DFA'd after a brutal 2024 and a rough start to 2025, but he has a 1.88 ERA in 30 appearances since his recall from Triple-A and has settled back in as the Pirates' closer. He had a very long rough patch, but Bednar is looking like the dominant closer he was not too long ago.
Adding an arm of his caliber, who also happens to have an extra year of club control, to a bullpen that's already underratedly deep, would be awesome. Unfortunately, the thing that's standing in their way of getting Keller would also make it a challenge to acquire Bednar.
Cubs face an uphill battle to acquire dream deadline duo
Cubs fans are familiar with both Keller and Bednar largely because those two players play for a division rival. The Pirates will obviously be deadline sellers, and they might be willing to part with Keller and/or Bednar, but how sure are we that they'd be willing to trade them to Chicago?
If Keller and Bednar were on expiring deals, perhaps this would make sense. It's never fun to trade with a division rival, but it's not as if they're competing for anything this season. Trading players with more than a couple of months of club control to a division rival is a much-harder sell, though.
Is this a possibility? Perhaps. To get a deal done, especially for both of them, the Cubs would theoretically have to outbid the field significantly. Doing so might be wise for Chicago, given how good their offense is and how well those two pitchers would fit. Whether they'd be willing to do so, though, and whether the Pirates would even entertain the Cubs, remains to be seen.