Clock Officially Ticking on Cody Bellinger’s Decision, Cubs’ 40-Man Moves

The Dodgers are World Series champions, proving once again that all you need is a little pluck, good chemistry, and over a billion dollars in free-agent acquisitions to win it all. And though Jesse Rogers may continue to share stories about the moronic Yankees fan who attempted to help his team by ripping a ball away from Mookie Betts, most folks have now turned their attention to the offseason. The Cubs have a lot to accomplish with several moving pieces in play, and several of those pivotal decisions need to be made soon.

Contracts officially expired at the conclusion of the World Series, but players can’t sign with new teams for five days. That line of demarcation at 4pm CT on Monday also applies to qualifying offer extensions, exercising options, and the expiration of 60-day IL designations. That last one is very big for the Cubs, who will see eight players added back to the 40-man roster with only three or four free agents dropping off.

Let’s get to Bellinger first, as his decision is the most pivotal here. I’m in the minority when it comes to saying he’s likely to choose free agency, but a growing number of voices are joining the chorus. MLB.com Cubs beat writer Jordan Bastian noted recently that “the general belief is that Bellinger will opt out and hit the free-agent market again this winter.” Sahadev Sharma shared very similar thoughts on the North Side Territory podcast, saying the “general feeling is that Cody Bellinger opts out.”

My opinion is based primarily on circumstantial evidence, but I’m going to go out on a limb and say that a pair of beat writers are privy to a little more than that. Even though nothing is firm yet, I can’t imagine the Cubs are willing to negotiate a longer deal with Bellinger over the next few days of exclusivity and he’s probably looking for more security than he’s currently got. Don’t fool yourself into believing it’s just about doing better than his AAV for the next two years, this will come down to whether he can lock up more money over a longer period with the ability to choose his destination.

As for the other pending free agents, those decisions are much cheaper and far less pressing. Kyle Hendricks already got a terrific send-off late in the season and will likely be given a chance to see whether another team is willing to guarantee him a rotation spot and/or a multiyear deal. I could see him returning to the Cubs on an incentive-laden contract closer to spring training should something else fail to materialize.

Jorge López pitched very well in Chicago after falling out of favor with the Mets and the two sides might be open to a reunion, but this feels like another one in which the righty will be allowed to explore his market first. Drew Smyly is the only one for whom I’d say the ship has sailed. He probably prefers a starting role the Cubs aren’t going to give him and the front office can upgrade that long-relief spot at a much lower cost.

Now we turn to the 60-day IL group of Yency Almonte, Adbert Alzolay, Colten Brewer, Ben Brown, Luke Little, Julian Merryweather, Nick Madrigal, and Brennen Davis. The Cubs will need to do something with at least four of these players, which isn’t actually that difficult a decision from where I sit. My guess is that they’ll drop the first three listed and Madrigal. Davis is very much in danger of leaving the organization as well after seeing his season ended by yet another injury in a string of them over the course of his career.

There could be some mixing and matching here as well, since Almonte, Alzolay, Brewer, and Madrigal are all arbitration-eligible. The Cubs love to delay any permanent roster decisions for as long as possible, so they could choose to keep one or more of those players around until at least the November 22 non-tender deadline. That would likely be more procedural than anything, as I don’t expect any of them to remain on the roster into next season. Do keep an eye out for a return or two on minor-league deals, though.

Of course, just trimming the roster back down to an acceptable number isn’t going to be enough. The Cubs have a lot of work to do and will need to clear several more spots for external additions and internal promotions. That pool of 14 arb-eligible players will get quite a bit shallower in a few weeks, with at least four others being trimmed in addition to those named above. As I predicted earlier this month, there’s a strong possibility that Christian Bethancourt, Jimmy Herget, Patrick Wisdom, and Trey Wingenter are not offered contracts for 2025.

Given how long they’ve had to figure this all out, I have to think Jed Hoyer and Carter Hawkins have already made all of these decisions. I imagine Cody Bellinger has also made up his mind, and that the Cubs are aware of what he’s planning to do. Does that mean other dominoes will start falling quickly once the five-day wait is over? Doubtful, unless Juan Soto breaks with recent trends and makes a hasty decision to stay in New York.

At the very least, we’ll get a little more clarity about the Cubs’ direction once we know for sure about Bellinger. Well, sort of. His departure could mean they elevate Owen Caissie to Chicago or it could have them looking for more certainty, particularly in terms of power output, with someone like Anthony Santander. Let the speculation begin. Or just continue, whatever.