Mookie Betts Reportedly Wanted an Extension Closer to Trout Money Than Harper/Machado Money

It hasn’t been easy to keep our sanity this offseason, not as the Cubs have been more or less strategically encouraged not to spend in the near term. But one thing that’s tickled at the back of my mind is the hope of a relative spending spree next winter. After all, there’s not much point in resetting your luxury tax penalties right now if you don’t intend on blowing past them next time around, right? I mean … that is a key part of The 2020 Plan, right? The Cubs have spent well beyond the luxury tax before, right?

Anyway, I’m currently hoping that is part of the Cubs’ intention as they chart out the next few years. And with the 27-year-old, Theo-Epstein-drafted Mookie Betts heading into his final year before free agency, I’ve even allowed myself to think, specifically, about whether the Cubs could pursue him next year if they open up the checkbook.

With that said, I never had any illusions about Betts’ likely huge price tag. I know it’s going to cost a lot – there are rarely free agents as good and young as he is – but I also know the Cubs (1) will have even more money falling off the books next season and (2) might be on the doorstep of shipping some salary out the door this offseason. There should be considerable financial flexibility. Heck, there ought to be by next year.

But even with all of that in mind … I was still WAAAAAY underestimating what it might take to get Betts.

Per Rob Bradford, on previous extension talks with the Red Sox:

“It is believed that Betts’ asking price may have been closer to Mike Trout’s 12-year, $426 million deal than the contracts given to Manny Machado (10 years, $300 million) and Bryce Harper (13 years, $330 million), which is why a deal didn’t get done prior to the 2019 season. But the Red Sox still haven’t given up hope that they can keep Betts around past the 2020 season, still weighing incoming proposals from other teams to see if any jump off the page.”

So if Betts was looking for Trout-level money last year, the asking price in free agency might gargantuan.

Betts was likely headed for at least $300M in free agency as soon as Bryce Harper ($330M) and Manny Machado ($300M) signed their free agent deals last winter, and that’s all but guaranteed now that teams have confirmed the normalcy of these new FA levels with Anthony Rendon ($245M), Gerrit Cole ($324), and Stephen Strasburg ($245M). In terms of talent, Betts absolutely belongs in this tier. And in terms of age at the time of free agency, he’s younger than all but Harper and Machado. Giving him $300 million would still be a risk that only a few teams could take, but it’s also probably the floor for any deal he’d accept (presuming he has a good and healthy 2020 season).

Giving him $400M on the other hand? Yowsa. That might require some serious consideration.

While it’s true that Mookie Betts (35.4 WAR) has been second only to Mike Trout (44.2 WAR) in WAR since his first full professional season in 2015, the gap is obviously still quite large. Indeed, I think I can explain the difference with a little world play:

This is an oversimplification, but it’s true and it’s important. To put it another way, Trout has never posted a full season with less than 8 WAR … Betts has exceeded that level only twice. In other words, Trout is *always* super elite. Betts has been super elite twice and has otherwise been merely really, really good. Again, you may find that distinction subtle. When it comes to the very top tier of spending, it is not.

Betts is very good offensively and defensively. No question. He adds in great baserunning ability, some versatility, and extreme likability/marketability. Together, that might be enough to help him earn more than the deals for Machado and Harper (even though they were two years younger at the time of signing). Absolutely. 100%. Fast-forwarding a couple years into the future helps, too, as dollar amount of deals just typically increases over time. But if he’s really asking for Trout-level money right now, I can understand why the Red Sox would be reluctant to give it before they absolutely had to.

And that hits with even more Cubs implications than just the meatball-y “Oh darn, I guess we can’t sign him now.” 

For example, is it possible that an extension for Kris Bryant or Javy Baez this offseason is just entirely out of the picture even if the Cubs are able to move some salary by way of trade? If the market has really exploded to this extent, some past extension comps could be completely useless for star-level players.

Heck, note Bryant’s placement on that previously-mentioned 2015-19 WAR leaderboard:

1. Mike Trout: 44.2 WAR
2. Mookie Betts: 35.4 WAR
3. Kris Bryant: 27.8 WAR
4. Christian Yelich: 27.7 WAR
5. Josh Donaldson: 27.6 WAR

Obviously things like age, recent performance, health, position, willingness to extend in Chicago, etc. all matter, but it’s not difficult to imagine the calculus on Bryant, specifically, changing dramatically over the past year or so.

And, even after a season that didn’t match his MVP runner-up showing in 2018, Baez’s thinking might have changed, too.

For a while, I was confident that an extension for Baez was going to follow something along the lines of the April 2019 extension for Xander Bogaerts (6 years, $120M). They’re similarly aged, skilled, and positioned, with Baez just having one more year of control than Bogaerts did at the time of the deal. But now? If this is what it takes to get Betts? And if Anthony Rendon is pulling in $245M? Is it crazy to suggest Baez would ratchet up the demands considerably?

The Cubs might not be able to extend Javy Baez *and stay under the luxury tax threshold this offseason* even if they move out some money.

The unfortunate truths:

1. The Cubs are already right at the luxury tax threshold, and
2. The Cubs must go under this offseason* if they want to avoid compounding penalties next year.

*I would have argued (and I did) that going all-in again on 2020 could make sense, given how many prime-aged seasons are at stake, but with so few options left in free agency, there really is no other choice or the Cubs now. They committed to this path. It kinda has to happen. Ending up just a couple million over the threshold at this point would be a disaster if it were paired with a meh season in 2020 AND an inability/unwillingness to spend big in 2021 AND no long-term pieces added.

In any case, we’ll have to wait and see what happens, though I think it’s pretty simple. If Betts has another one of his “elite” seasons in 2020, something close to Trout money could be a realistic ask. If he just has another really good season, something in the $275-$325M range is probably more likely. In the meantime, the implications might be hitting the Cubs no matter what, and their long-term plans (from internal decision to external targets) may continue to evolve.

Brett Taylor contributed to this post.