Nicholas Castellanos offered a much-needed bright spot the otherwise dreary stretch run for the Cubs, easily exceeding even the most lofty expectations for his post-trade performance. He reminded his new teammates what it looked like to be hungry and said the move to a contender was like coming up for air after being underwater for a long time. It was truly a mutually beneficial relationship.
A reunion seems like a no-brainer on the surface, given the Cubs’ desire to stay competitive and the obvious Castellanos’ derived from playing at Wrigley. But there are a few complicating factors, among them Scott Boras and the idea that the Cubs may be trying to shed salary. Boras isn’t exactly known for negotiating team-friendly deals, and Castellanos did a helluva job of making his agent’s job a little easier by showing out on a big stage.
At the same time, Castellanos is a contemplative cat who seems to have a firm grasp of the bigger picture and the value of happiness. He may be the kind of player who’s willing to take a little less in order to prioritize the best possible fit in an organization and/or city. That seemed to be missing from Bryce Harper’s courtship last season, with multiple reports claiming he preferred Los Angeles or Chicago before landing in Philadelphia.
The Cubs likewise saw how Castellanos brought a new energy to the field and clubhouse alike and they envision him as the kind of player who can help them build a new culture. That’s why they’ve reportedly made him the top priority among their internal free agents, with MLB.com’s Jordan Bastian writing that “there is mutual interest” in a return engagement.
That doesn’t mean a deal will be worked out as soon as free agency opens, or even by the time the Winter Meetings roll around in December. Boras is going to want to test the waters and Bastian writes that Castellanos will be “watching how the Cubs approach this offseason and factoring that into his decision.” Sounds like one of those deals where there’ll be some open communication throughout the winter, perhaps something where Boras gives the Cubs a chance to counter other offers.
As good a fit as Castellanos was, though, this still has the feel of something that isn’t going to happen. With other needs to fill and what sounds like limited means with which to fill them, the Cubs can’t very well view Castellanos as a necessary building block for 2020 and beyond. So even if he’s willing to take a “hometown” discount, the Cubs may not even have enough left for that after making other moves.
On the other hand, it’s entirely possible that even bigger free agency pursuits could tie Boras up and have Castellanos pushing to get a deal done. Boras also represents the Gerrit Cole and Anthony Rendon, both of whom figure to earn well over $200 million this winter, and he could be shopping Stephen Strasburg as well should the ace opt out of his Nats deal.
With those guys all drawing the attention of front offices and their agent alike, it’s possible Castellanos could simply want to get out of the fray and ensure he’s got a team before spring training opens. And not that Boras would ever be dismissive of a client just to get a deal done, but he might be slightly more amenable to a quicker negotiation in order to properly fry his other fish.
I’d say we’ll find out soon enough, but stuff like this may not be resolved very soon at all.