Coming Week May Redefine ‘Con’ in CubsCon

With just five days to go before the Cubs’ annual fan gathering in downtown Chicago, the team has yet to make a more significant move than claiming catcher Brian Serven off waivers. Sahadev Sharma wrote for The Athletic that the front office remains optimistic about the coming season despite the dearth of deals, which matches up with what we’ve been saying here for a while. But there’s more than a little restlessness among the natives, who see this lack of activity as a dereliction of duty or breach of trust.

So is Cubs Convention going to be defined by the team’s confidence or fans’ belief that they’re being conned, figuratively as well as literally? We may not know the answer until the Cubs report to spring training, or maybe even after, though reaching into an older regime’s bag of tricks sure would help.

The revelation that Kerry Wood was returning to the team in 2011, a reunion spurred in part by Ron Santo‘s passing a little over a month earlier, set a precedent that lingered for years. While the Cubs haven’t made nearly as big of a surprise announcement since, people still hold out hope for some kind of breaking news. Last year brought the announcement that Mark Grace and Shawon Dunston had earned entry into the Cubs Hall of Fame, then came word of Ryne Sandberg‘s statue.

Bringing Cody Bellinger to the stage on Friday night would blow the roof off the Sheraton Grand and could change the whole tenor of the team’s offseason strategy. Or rather, it would change the perception of the strategy. Jed Hoyer has adhered steadfastly to a value-based approach that prohibits stretching much, if at all, beyond the cost/benefit analysis of any free agent or trade target.

Such a process is great when it works, but there’s no way to judge its effectiveness when there’s been no activity to speak of beyond the surprise move to hire Craig Counsell. The two schools of thought at the time were that the huge splash following a clandestine pursuit meant the Cubs were either going to spend meaningfully to win in 2024 or that they were going cheap to let Counsell do what he’d done so often with the Brewers. The latter concept has gained far more credence in the time since that hire.

If we know anything about Hoyer, though, it’s that he’s stealthy and will move quickly to make things happen when he believes the deal is right. That doesn’t mean there isn’t plenty of due diligence, which is part of why so many potential fits remain on the market. The other part is that getting value is going to require waiting out Scott Boras on what could be a number of different free agents.

Another aspect of Hoyer that I think could contribute to the potential for a move or two this week is that he’s got a bit of a mischievous streak. Now, I’m not saying he would ever slow-play a deal just for the sake of generating hype at the convention. Nor am I saying that he’s signing minor-league deals and making waiver claims just to piss people off.

So while I highly doubt Hoyer is actually checking on fans’ responses to Serven, Joe Hudson, or Jorge Alfaro, I can see him getting a chuckle out of it. How could he not? Similarly, I’m sure he’d feel an extra boost of satisfaction if he’s able to rewrite the offseason narrative by inking a big free agent or two. Just to make this extra clear, I’m not saying outside opinions have any impact on how Hoyer operates. But he is going to face the media and the public on Saturday, and that will surely be a lot more fun if he’s able to address questions about how the team has improved.

I’m getting a strong sense that something could get done in the next few days, though some of that may just be my own optimism mixed with the knowledge that Hoyer has to do something. How about you? Do you believe Hoyer’s confidence will be justified or do you see him as merely a confidence man?

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