With the recent acquisition of Ryan Pressly, the Chicago Cubs' bullpen is now in a better place than it was just a year ago. They've also added a much-needed superstar bat in Kyle Tucker, and their top three in the NL starting rotation is still intact.
As it sits, the Cubs don't have significant funds left to play with this winter. It's been reported that $220 million was the cap on the offseason, and after landing Pressly via trade, the Cubs are just shy of $210 million in payroll.
That means you can forget about Alex Bregman, Jack Flaherty, and anybody who will take the Cubs over that $220 million mark, given the flexibility the team wants to keep for in-season acquisitions.
The bench is mainly set after the Cubs signed Jon Berti, so if anything, the Cubs may be looking to add one more key reliever to the mix. If the Cubs can sign one of these three arms, they will be in good shape and should be able to coast to the MLB trade deadline as buyers, where they can become strong contenders with the funds and prospect capital they will have available.
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1. Ryne Stanek
One of the more underwhelming connections to the Cubs right now is fireballer Ryne Stanek. Stanek recorded a 4.88 ERA in 2024, accompanied by a 4.14 FIP. Even though his FIP was lower in this case, I'm still not on board, given that better arms are available in the Cubs' price range. Stanek's production vanished after being traded to the Mets at the deadline, as witnessed by his 7.27 ERA in the second half.
If Jed Hoyer and the front office are eyeing Stanek, it's likely more than just for a discount compared to other relievers. The Cubs' pitching infrastructure is a strength within the organization, so they likely see something they can fix in Stanek. We're entering the third season since Stanek's other-worldly 1.15 ERA campaign, after two down seasons since the Cubs may be wise to go after someone a little more noteworthy.
2. Andrew Chafin
When the Cubs signed Caleb Thielbar, it checked a box for the Cubs that they desperately needed: a left-handed reliever. The problem is that Thielbar allowed 10 earned runs in 22.1 IP against left-handed bats in 2024, equating to an underwhelming 4.03 ERA. On the bright side, a 2.59 FIP against lefties is encouraging. Still, the Cubs could use a southpaw who's been a little more dependable, like Andrew Chafin.
Dubbed the "Sheriff," Cubs fans will fondly remember Chafin's time in Chicago during the 2021 campaign when he recorded a 2.06 ERA. Mainly serving as a setup man, that role could bring much value to Chicago, with Ryan Pressly presumable set to take over closing duties on the north side. Chafin had a good bounce-back year after struggling in 2023 and still owns a 3.42 ERA. There hasn't been a lot of smoke between the Cubs and Chafin's camp, but we will see if any rumors pop up over the next few days with the Cubs looking to add another bullpen arm.
3. David Robertson
My favorite name on this list is David Robertson. Another former Cub who put up good numbers in a Cubs uniform, Robertson, recorded a 2.23 ERA with 14 saves in 2022. Since then, between 2023 and 2024, he has recorded a 3.01 ERA in 137.1 frames. Although Robertson is entering his age-40 season, he still appears to have plenty in the tank and will have no problem finding a contract with a big-league club this winter.
Considering the Cubs still have $13 million before hitting that $220 million cap for the offseason, Robertson's price range likely falls in perfectly for the Cubs financially. Having a tandem of Robertson and Pressly not only gives the Cubs two guys who can close on any given night, but with Porter Hodge, Tyson Miller, and Eli Morgan in the mix, it gives the Cubs a surprisingly deep bullpen that would be vastly improved from a season ago.