The Advent of the Winter Meetings, the Urgency of This Offseason, HOF, Wicks, and Other Cubs Bullets ...Middle East

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All right. The holiday is here. The Winter Meetings. Time to start really popping off, baseball …

Speaking of which, I wrote yesterday about the prepared-for-urgency with which the Cubs need to treat this week, even if it may wind up that it isn’t absolutely critical to get things done SPECIFICALLY this week. In short, if dominoes do start falling in certain sectors, the Cubs may have to leap quickly. They have a set of needs, and if they have strong market preferences, they can’t let the moves pass them by while they wait to accumulate leverage. Something I was thinking about, but didn’t really find a way to fold into the post, is the specific importance of this offseason. Forget, for a moment, the specific importance of the Winter Meetings, and instead remember where the Cubs stand organizationally. They are coming off their first 90+ win season and playoff series win in a very long time. They have a roster that is built to win now, with a very clear opportunity in 2026. They have a half-dozen well-compensated players who are hitting free agency after 2026, and a clean set of books thereafter. They are facing a starting pitcher and relief market that are loaded with quality options at the very same time that they are in need of those categories of player. And they have a dearth of rising pitching prospects in the farm system overall. That is all to say: this offseason, the Cubs have a LOAD of reasons to be very active and very aggressive. That whole thing doesn’t start today or end on Wednesday. But if that’s when the market forces the issue, then so be it. The Cubs cannot let this offseason pass without making the right set of moves, because this particular offseason is so critical for the Cubs. Maybe that process kicks into high gear this week. Jeff Kent got more than the 12 (of 16) necessary votes from the Contemporary Baseball Era committee to enter the Hall of Fame, and here’s how the rest of the voting went:

The full results of the Hall of Fame's 2025 Contemporary Baseball Era ballot voting. pic.twitter.com/iqrcGI9zxM

— MLB Network (@MLBNetwork) December 8, 2025 Each of Carlos Delgado, Dale Murphy, and Don Mattingly at least have an argument to be made, and each arguably had bigger peaks in their career than did Kent. But Kent did it at a more difficult defensive position, did it so consistently for so long, and in my view did have the edge on those three. To be sure, I think all four would fall just short for me, personally, but if the committee had to pick only one, I think they probably picked the right one (with particular apologies to Delgado). The whole thing is making me think about what a crime it is that Bobby Abreu can’t even get 20% of the vote. The sub-5-vote group, which includes Barry Bonds and Roger Clemens, is collectively ineligible for consideration during the committee’s next vote in three years. So they would have to wait an additional three years thereafter to get on another ballot. A wild ride about the potential subterfuge happening behind the scenes, even years ahead of free agency, and with allegations flying on all sides about who said what and when:

Sonny Gray told people behind the scenes that he badly wanted to get traded to the Yankees in 2017, Brian Cashman said.The problem? Cashman says Gray told him he was lying to look better for free agency and never wanted it to actually happen.READ: t.co/3RfTMuwaMK

— Brendan Kuty ?‍♂️ (@BrendanKutyNJ) December 8, 2025 Although denied by Gray’s agent, supposedly Gray was telling lower-level Yankees folks, at the time he was with the A’s, that he really wanted the Yankees to trade for him. Which was apparently a lie, driven by a desire to keep his market wide open when he eventually reached free agency – you don’t want any suitors to know there are places you definitely wouldn’t go. Whether that story is all true or not, consider it a reminded warning: when you hear a rumor about discussions behind the scenes, it can be accurate that those discussions happened … but, even if it was actually said and accurately reported, it could have been a strategic lie! The context here is that Gray was uncharacteristically abysmal in New York, where he was apparently miserable. He was later traded to the Reds (where he immediately signed an extension), then the Twins, and signed with the Cardinals – all smaller markets where he pitched quite well. So how will things go in Boston? We’ll see. At least he gets to hate the Yankees publicly now. And the Cubs kept bringing him up as a reliever instead of just letting him stay on schedule and using him for an occasional spot start (which would’ve fit multiple times throughout the year):

Friendly reminder that Jordan Wicks was REALLY good in Triple-A this year

— Greg Huss (@outofthevines.bsky.social) 2025-12-02T18:28:30.911Z Jordan Wicks, assuming he isn’t traded sooner, will enter Spring Training as starting pitching depth for the Cubs, given that he’s still got option years remaining. Realistically, the Cubs are going to build out their rotation such that Wicks would be seventh or eighth on the depth chart in March, though injuries do happen, as we saw last Spring. All I’m saying is that if the Cubs are going to consider Wicks as depth anyway, then USE HIM as actual STARTING PITCHING depth. His stuff just doesn’t seem like a good fit as a reliever, and we know that the double yo-yo (minors to bigs and back, starting to bullpen and back) is exceedingly difficult for any pitcher to pull off, let alone a guy trying to establish himself. There’s a capable 4th-ish starter in there already. I know it. Let him be that guy as depth for when you need him. It’s actually kinda terrifying to see these guys hit with metal bats:

Metal bats + big sluggers=??Vladimir Guerrero Jr. and other stars were letting it rip during the La Gente del Barrio Foundation Home Run Derby at loanDepot Park in Miami! pic.twitter.com/dN3Xv1qPu6

— MLB (@MLB) December 7, 2025 MORE CUBS FROM BLEACHER NATION: Go Ad Free | Subscribe to the BN Newsletter

WordPress has me down for 1,007 words on the Bears loss to the Packers over at @BN_Bears:? Immediate post-game thoughts & reactions? Highlights (and, sigh, lowlights)? What's next? t.co/1MFla5xOM8 pic.twitter.com/5Foi6qasBk

— Funky Cold Luda (@lcm1986) December 8, 2025

Bears Nightcap: Bears Stumble in the Rivalry, Steady in the Bigger Picture t.co/pxzdfBqcv3

— Bleacher Nation Bears (@BN_Bears) December 8, 2025

Blackhawks 1, Ducks 7 — Three Stars, Key Takeaways #blackhawks t.co/JgEmG8p5Vd

— Bleacher Nation Blackhawks (@BN_Blackhawks) December 8, 2025

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