Get What You Need

Take what the market gives you

We’re a few days from the winter hot stove market really getting going, and once it does, I expect we’re in store for a unique offseason. A looming work stoppage after the 2026 season means we will probably get a few teams fully going for it in the coming year, knowing that baseball might shut down for some amount of time. And then we will likely have quite a few who are going to try and hedge their player investments, knowing that committing to a lot of long-term deals could mean losing years of those contracts because baseball isn’t being played.

The potential for a work stoppage after next season is going to add complexity to the winter free agent and trade markets, a time that is usually rife with enough complications on its own. Nevertheless, teams are going to have to navigate the coming months how they see fit. For now, I have thoughts on the Cubs specifically.

They are in prime position to take an important step forward, but whether or not they do will depend largely on what happens this winter. The Cubs improved by nine wins in 2025 over the previous two years and won a postseason series for the first time in eight years. They could be poised to get back to the top of their division and make an even deeper run in the playoffs next year. It would be a shameful waste of that opportunity not to be aggressive this offseason.

I wrote last week about the Cubs’ financial advantage — one that they don’t seem to want to take full advantage of — but here’s the thrust of it:

They have revenue that rivals Los Angeles, a market that would support increased spending, and just as rich a legacy in the sport. And yet there’s a nearly $200 million gap between the Dodgers’ 2025 payroll and the Cubs’. There are big market teams trying to compete with what the Dodgers doing, like the Mets, Yankees, and Phillies, who all spent over $300 million on their teams last season. Where the Cubs were very clearly aiming to stay below the $241 million luxury tax threshold, eight other teams went right past it. Some of them by a lot.

And of the teams that reached the postseason this year, only a handful had total team salary commitments under the luxury tax threshold. To put it another way: You spend, you (probably) win. In Major League Baseball, frugality is the path to failure.

Assuming that the Cubs will not sit idly by as the winter passes, the problem they might encounter could be that they can’t make the kinds of moves I think they need, but will instead have to respond to what the market is offering.

Here’s what I mean: