Can We Let Ourselves Think About the Cubs Re-Signing Kris Bryant After This Season?

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Can We Let Ourselves Think About the Cubs Re-Signing Kris Bryant After This Season?

Chicago Cubs

I’d had a few articles open in tabs for a week or two, just sitting there up top on my screen. I didn’t really want to deal with them. I knew they could be talking points for a post, but I just … it wasn’t time. I knew it wasn’t time. And I sure didn’t feel any kind of special passion about making it time just yet.

The topics of those tabbed articles?

Trading Kris Bryant.

I get it, and certainly I participated in the offseason (just as I will later this year if it comes to that). Bryant, an impending free agent, is having a great year while his team may not be. He’s been exposed to the trade market, reportedly, for multiple years now in the offseason, and it was only a matter of 2021 arriving before he was going to be exposed in-season, too. I poo-poo no one for getting into it.

It’s just that didn’t want to get into it yet. Realistic trade rumors aren’t going to emerge for several more weeks, and even that would come only after the Cubs and potential buyers “declare themselves,” so to speak. These Cubs still have a chance to win the NL Central – or, more importantly, to look by late June like they definitely could win the Central. Can’t we stay in that zone for a little bit longer before flipping the switch? I promise you, when the time is right, I’ll flip the coverage switch and we’ll be rumor central (in hopefully an engaging and informative way!). But not early May, man. Not early May in a year where the Cubs may not ultimately sell off. I still think it’s probable that they do – sorry to say – but Jed Hoyer and the front office are leaving the door open for a little while longer, and I’ll do the same.

So it was with some relief that I saw Patrick Mooney today taking a different tack with the Kris Bryant stuff. Sure, it strikes me as pretty darn unlikely at this point, but I’d love to take a breath and think about what it might look like if the Cubs did try to keep Bryant after this year, even if it was a matter of taking things to free agency:

No one is expecting a surprise extension for Bryant at any point during the 2021 season, so if the Cubs are going to have him in the lineup come 2022, it’s probably going to have to come by way of a free agent rumble.

Bryant, you’ll note, has always expressed his affection for Chicago and the Cubs, even as there was obvious friction about his service time. The longstanding presumption that he would (1) not be extended, and (2) would hit free agency to depart for another club has been based on a variety of factors, but it was never that Bryant just clearly flat-out wanted to leave as soon as he could. So that’s a start.

But those other factors were always an issue in extension talks, and we should at least touch on them (as they still kinda inform the free agency discussion, too): for example, Bryant’s ceiling was so high and his career earnings so significant that he was unlikely to extend unless it was just a monstrous, free-agent-level sum (which, in turns, moves the ball forward for other players down the line – something Bryant cares about). The times when Bryant did deal with injury issues and/or uneven production, it came in periods where you otherwise would’ve been looking to extend, helping – I suspect – to muck up those extension chances. Bryant is not old, but his first free agent year will be his age 30 season, which is also a factor in making long-term deals more of a challenge to find the right level for both sides.

And when you throw in free agency getting closer and closer, the likelihood that a player and a team can find the right price tag in those final months of team control diminishes further. A whole lotta teams are going to want to take a shot at signing Bryant, and when he’s a full-on free agent, he’s going to get top-of-the-market dollars *AND* get to choose where he wants to go. Maybe it would be a reunion with the Cubs. Maybe it wouldn’t. And maybe the Cubs won’t be near the top-of-the-market in offers anyway.

Like I said, at least there’s the starting point where Bryant has always expressed happiness with the city and the Cubs. Could the Cubs actually take this thing to free agency with Bryant, and then pony up to sign him to a, what, seven-year, $200 million deal? More? They’ll have the slight advantage of having made him a qualifying offer, so, in theory, their “cost” to sign him would be slightly less than another big market team that would have to give up draft pick compensation and IFA bonus pool space to sign him (whereas the Cubs would only be “losing” a compensatory pick after the second round). Also, obligatory: The expiring CBA is going to complicate any of these discussions, so you kinda just have to accept that it might mess everything up.

The Cubs will have wiiiiiiide open books after this season, with Jason Heyward, Kyle Hendricks, and David Bote the only players on guaranteed years in 2022. There are arbitration raises coming for guys like Willson Contreras and Ian Happ, but the upshot here is that the Cubs should have plenty of money available in 2022 for any signing they want, especially if Hoyer’s comments about the Cubs getting up back toward the luxury tax level in the coming years was accurate.

So, then, the Cubs might have a slight edge relative to the market, and they’ll certainly have the dollars available. Why can’t they be in the mix to sign Bryant in free agency?

Here’s how Mooney puts it:

Bryant’s MVP candidacy won’t generate a lot of momentum when he’s playing on a 17-19 team and working for an organization that will take a clinical approach to the trade deadline. But as long as he stays healthy, the Cubs will have to consider the idea of trading him this summer and trying to re-sign him as a free agent next winter, however remote that possibility may be, because it is really hard to find really good players.

Yes. The Cubs will have to consider it.

I think it’s fair to let yourself linger there. But what I would urge you to keep in mind is that, again, once a player actually reaches free agency, he’s able to choose from that big pool of possible new teams, where the dollars might be similar and where there might be other preferences at play. Or maybe some owner like Steve Cohen has just decided that BRYANT IS THE GUY, and he goes way over the top to get it done. You just don’t know how it’s going to go once it’s all opened up like that.

Oh, also? If you’ve traded the guy to another club at midseason, then you really, REALLY don’t know how it’s going to go. Back when the Red Sox traded Jon Lester to the A’s in mid-2014, and then tried to sign him in free agency, I remember reading that he remarked something like going to that other club – the A’s – kind of showed him, in general, how it was going to be OK if he was with a different team after free agency. And that, not any bitterness toward the Red Sox about the trade, made it more likely he would sign elsewhere, which he obviously did with the Cubs. So that’s another consideration in all of this with the Cubs and Bryant in free agency.

Not that I’m thinking about Kris Bryant trades yet. *closes all those tabs*

Author: Brett Taylor

Brett Taylor is the Editor and Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and @Brett_A_Taylor.