Chicago Cubs 2016 NL Central Championship Gear

jason heyward cardinalsI have to keep telling myself that, with respect to any free agent, even with an aggressive pursuit, you cannot guarantee that you’ll land the guy you want. Not only does there have to be a line somewhere financially, but it tends to be the case that guys you really want will also be wanted by other teams. Some of those teams have lots of money, are also good at baseball, also play in lovely cities, and also offer opt-out clauses and no-trade clauses and what-have-you.

Nothing is guaranteed, even when the chase begins.

However, I am very pleased to see confirmed something we’ve been hoping for a long time: the Cubs are definitely pursuing Jason Heyward.

That comes via multiple reports (Mooney, Rogers, Kaplan, Wittenmyer), all of which more or less indicate that, not only are the Cubs legitimately interested in actually landing Heyward, but also that it’s actually possible.

Now, then, no one is laboring under the assumption that the Cubs can just write a check for $230 million right now and blow away the field for Heyward. It’s more likely that the only way this can happen is if (1) Heyward is sold on the idea of coming to the Cubs, specifically, (2) the contract is structured in a way to minimize the near-term financial impact, and (3) the Cubs successfully pull off some other maneuvering to make Heyward fit.

On that last one, we’re already seeing a portion of the activity, and it’s something we’ve discussed for a while: if the Cubs are able to pick up the type of controllable, impact pitching they seek in trade, they have more flexibility (financially) to add a contract like Heyward’s. Having already signed John Lackey to a reasonable contract, the Cubs gave themselves plenty of cover to target pitching trades (which are, obviously, much less certain than free agency) so that they could then turn to the outfield in a more aggressive way. This was pretty clearly their preferred series of moves for this offseason, which could have gone so many ways.

The other possible maneuvering we could see to make Heyward more possible is, of course, purely financial. Could the Cubs try to move contracts like that of Starlin Castro or Miguel Montero or Jason Hammel?

Well, on Castro, we’ve seen rumors already this offseason, and I still tend to think he has actual value on his current contract in this market (either to the Cubs or in trade). On Montero, we’ve also seen some rumors, but I struggle with the idea that the Cubs could adequately replace Montero’s value behind the plate if they decide to move him (because surely the Cubs can’t be comfortable with turning, right now, to Kyle Schwarber or Willson Contreras as the full-time starter there). On Hammel, I’m sure there would be teams happy to bring in a guy like him on a very affordable, one-year contract, even after his second-half struggles. But would the Cubs trade from their pitching depth like that right now? And would they trade a guy who just last year at this time signed a very reasonable deal because he so much wanted to return to the Cubs? Sure, the team has to do what it has to do, but there’s a human element at play, too.

There are a lot of intertwining parts here, and I’m not sure it’ll all be sorted out this week at the Winter Meetings. It seems likely that the first step (well, the first step after Lackey) will happen this week, with the Cubs possibly picking up a younger pitcher in trade. From there, look for rumors on some of the Cubs’ bigger contracts to pick up, as well as chatter on Heyward, both from the Cubs and other teams. The outfield market, on the hole, has been a little slow to develop, and it wouldn’t surprise me if it’s because the Cubs, and some other key free-agent-seeking teams are sorting out what kind of financial might they’ll have at their disposal first.

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