2 offseason moves so far that Cubs fans are wishing Chicago had pulled off

The Chicago Cubs have made a handful of moves in the bullpen, bringing back veteran Caleb Thielbar, signing Phil Maton to a two-year deal and adding quirky southpaw Hoby Milner, but have steered clear of the top of the market, with few legitimate options left on the board with 2025 drawing to a close.

The depth chart, as currently constructed, has Daniel Palencia re-assuming the closer's job next spring - one he thrived in for much of the year. The hard-throwing right-hander posted a 2.91 ERA in 54 appearances, In save situations, he punched out 39 in just 30 innings of work, giving Craig Counsell a big arm to turn to in the ninth.

That's not necessarily a bad thing, but having Palencia slotted in as your swing man, capable of putting out fires as needed - a role he took on late in the year and during the Cubs' postseason run - would be a real difference-maker. Instead, Jed Hoyer has walked big name after big name sign, content to stick to his guns in terms of perceived value.

But imagine, for a second, the Cubs had assembled a super-pen; not quite to the extent of the Dodgers, who are throwing hundreds of millions of dollars at their collective group of relievers, but still a feared group capable of locking down games.

2 big bullpen arms that would have made a huge difference for the Cubs

Brad Keller

Brad Keller, a huge piece of the team's 2025 bullpen success, is off to Philadelphia after signing a two-year, $22 million deal this week. That's hardly a massive sum of money, especially for a team like the Cubs, but they were content to watch him walk even after helping him unlock something this year with pitching coach Tommy Hottovy.

The big righty posted a 2.07 ERA/2.93 FIP in 68 appearances, taking over the closer's job late in the season and into October after Palencia hit the shelf with an injury. He was huge in the postseason, allowing just one run in 5 2/3 frames. Bringing him back would have given you two ninth-inning options (which, again, we saw how important that can be this season) and made you feel a lot better about the Cubs closing games out in 2026.

Devin Williams

On a similar, albeit more expensive, note, Devin Williams reportedly wanted to link up with his former manager in Counsell at Wrigley Field. Despite mutual interest, the market got too rich for Hoyer's taste and, again, the Cubs dropped out of the running as the two-time All-Star and Reliever of the Year signed a three-year, $51 million deal with the Mets.

Now that's not the value that Keller's two-year, $22 million contract with Philly represents, but it's really just the message that doesn't sit well. He wanted to be a Cub, but the team wasn't willing to do what it takes to land one of the market's top relief options who, admittedly, is coming off a down year, but is just one season removed from a three-year run in which he allowed all of 26 earned runs in 148 appearances.

The Cubs haven't had a reliever like that in a long, long time. And given recent trends, that wait will continue for some time longer.