Bringing Nick Castellanos Back to Chicago Might Require a Surprisingly Aggressive Pursuit

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Bringing Nick Castellanos Back to Chicago Might Require a Surprisingly Aggressive Pursuit

Chicago Cubs

When the Cubs chose not to even attempt to re-sign Nick Castellanos after the 2019 season, it was a mistake. Potentially a costly one, considering how things have gone for his production trajectory, and how things went for the Cubs. (Or maybe he simply would’ve become a trade piece this past year …. )

In any case, since he signed a deal with the Reds that included not one, but two opt-outs, there has been a hopeful undercurrent in Chicago that Castellanos could eventually return to the North Side, where he himself said he had the turning point of his career.

Well, his first opt-out came after 2020, and given the uncertainty throughout the league due to the pandemic and an average overall season individually, Castellanos played it safe by deciding to stay in Cincinnati. One opportunity down. But his second and final opt-out is due five days after the end of the 2021 World Series and this time, he’s expected to leave … right?

On the one hand, it’s easy to look at his production (.309/.362/.576; 140 wRC+), age (29 until March), and limited remaining dollars ($16M in each of 2022 and 2023, plus a $20M mutual option in 2024 ($2M buyout)) and say “Well, of course, he’s going to opt-out.” And, yeah, I tend to think that’s correct.

But on the other hand … I just can’t underscore enough how much the CBA negotiations have everyone spooked. Take this comment from Castellanos, via The Athletic:

“I don’t know what I want,” Castellanos said. “I haven’t had these lengthy conversations with (wife) Jess, you know. I haven’t had any conversations about this with (agent) Scott (Boras). I mean, there is so much information that I’m going to take in. I also have to take into mind the status of the game. The collective bargaining agreement is now coming up….”

“It’s a balance of all of that, which will make the best decision possible. It could very well be here in Cincinnati. The bargaining agreement could go to shit and I’m not in a spot to opt out, so I have no idea what’s going to happen.”

There’s also the fact that when he does opt out, he’ll be eligible for a qualifying offer, which the Reds will give him and which he will decline, attaching him to draft pick compensation for whichever team does land him. Even if the CBA rules change this part of free agency, this group of players will likely be grandfathered in for this final offseason. (The only hedge here is the *possibility* that only the benefit of the rule will be grandfathered, rather than the loss of picks, but for now teams have to proceed on the assumption that the full rules will stay in place.).

Note: The tough thing for Castellanos is that there will not be a new agreement in place by the time his decisions – opt out and qualifying offer – are due, so he’ll have to roll the dice one way or the other. But again, with just $34M guaranteed ($16M for each of 2022 and 2023, plus a $2M buyout on that 2024 mutual option) … it’s pretty easy to guess that he’ll beat that no matter what, and a $19-ish million qualifying offer for 2022 isn’t really any better.

To be sure, you’re a little more comfortable giving up a draft pick (and IFA pool space) for a guy you’re expecting to sign to a long-term deal, but it’s definitely a non-zero factor. And for the Cubs, who have their highest relative pick in each round of the draft since 2014, it’s something to consider.

Going further with the Cubs’ involvement, they have openings all over the outfield and (theoretically) at designated hitter plus a TON of payroll space and a need for power in a lineup that does finally figure to have some contact throughout (Nick Madrigal, Nico Hoerner … Frank Schwindel?). However, their ENORMOUS needs in the rotation are expected to trump their efforts elsewhere. They also arguably still need a full-time shortstop and maybe third baseman, too. It’s a very needy roster, and a turning-30-year-old-bat-only guy might not be a primary focus. There could be clubs out there that see him as a “final piece,” and really ball out.

So while Castellanos fits positionally, financially, and perhaps especially in a marketing sense (the Cubs have some goodwill to buy back after this past deadline), it’s not so easy to see them leading the charge on Castellanos if he winds up seeing massing, long-term offers out there. Which, well, would be disappointing.

And let me phrase that another way to be clear: the Cubs should be involved on Castellanos. I think he’d be an excellent target for so many reasons, on the field and off, but whether they will seems to depend entirely on how his market shakes out. The Cubs keep telling us they intend to be opportunistic this offseason, not aggressive. So a big early push by the Cubs, a huge offer, and a disregard for the draft pick/IFA money considerations, would be at least a mild surprise.

There’s also the fact that Castellanos is one of the more outwardly competitive players on the market and he might not view the Cubs as his best chance to win in 2022. So not only could they have trouble convincing him to make Chicago his last big score, but other teams will get their chance to woo him, as well.

In fact, it’s already starting. For just one example, on his Swings and Mishes podcast, Craig Mish mentioned that the Marlins could be in the market for (South Florida native) Castellanos. And that squares with recent comments from GM Kim Ng: “We are going to have some money to spend. … We feel that we are primed to do very well with the pitching set up as it is and with us being able to spend some money on bats this offseason.” And CEO Derek Jeter backed that up: “For the first time really since we’ve been here as an ownership group, I expect to be pretty active (in the offseason).”

There will be a large number of suitors for Castellanos. I hope the Cubs are among them. I have my questions, though. We’ll see how the early part of the offseason shakes out, how the CBA talks are going, and what happens with the opt-out and the Qualifying Offer process.

Nick Castellanos is 10th on the updated MLB Trade Rumors Free Agent Power Rankings and would likely be the best positional free agent you can realistically expect the Cubs to engage on any level.

Brett Taylor contributed to this post.

Author: Michael Cerami

Michael Cerami covers the Chicago Cubs, Bears, and Bulls at Bleacher Nation. You can find him on Twitter @Michael_Cerami