Tyler Chatwood’s Reworked $38 Million Contract Still Biggest of the Offseason

Tyler Chatwood’s new contract has raised eyebrows this offseason, but not for the reasons you might expect. The inclusion of an escalator clause tied to Cy Young votes caused something of a kerfuffle among the Baseball Writers’ Association of America, which didn’t want even the slightest whiff of impropriety when it comes to their voting process.

While it’s perhaps a little overprotective and knee-jerky, this isn’t a new stance. The BBWAA had objected to a similar clause in Curt Schilling’s 2007 pact with the Red Sox and went so far as to ban him from Cy Young eligibility, something they threatened in Chatwood’s case. Then the MLB players’ union clapped back and the sides reached a tacit agreement to lift the ban with the understanding that such language would not be used again.

It’s no coincidence that the Chatwood snafu is the first recurrence of this issue in the last decade, as Theo Epstein and Jed Hoyer presided over Schilling’s deal as well. You’d think they’d have learned their lesson in the meantime, but it’s not like they were trying to pull one over on the intrepid journalists of the BBWAA. This was really about adding in an easily achievable incentive.

MLB does not allow teams to use ERA or wins and losses to trigger incentives, so teams will often go with All-Star appearances or innings pitched or even placement in end-of-season awards voting. By giving Chatwood an extra $2 million in 2020 for a Cy Young vote in either of the next two seasons or $4 million for a vote in each of the next two years, they were hoping to simplify things. You know, by not tying the salary to, say, a seventh-place finish.

Obviously it didn’t work out that way and all the parties involved got together to amend the contract language. While we don’t know exactly what changes were made, it’s probably safe to assume that the escalator is tied to rank in the voting rather than the votes themselves.

“If this is the one that brings this subject to a head, I’m OK with that,” Hoyer said Tuesday. “I just hope that the writers will come up with something else that teams are able to use in order to put in contracts. I think we can write better contracts, that we can be more creative if there are ways to qualitatively measure a player.”

Now that we’ve gotten that out of the way, let’s talk about how this contract, which ranks 99th in the list of most lucrative deals in baseball, is the largest one signed so far this offseason. None of the 98 contracts with higher value were signed since the 2017 season ended and the next-highest of the current free agency period belongs to Mike Minor, whose $28 million pact ranks 125th.

That’s crazy, right? I mean, there are surely some below Chatwood on the list that contain other incentives and options that could move them up the list, but we just talked about how Chatwood could still earn another $4 million as well. And that would push him all the way up to a tie for 92nd on the list.

I think we all understand that Chatwood is going to move quite a bit further down in the rankings once some of the big deals start to pop, so this isn’t some referendum on a sweeping change in baseball. It is, however, another sign that the buyer’s market has mucked things up a little bit for the top free agents.

Since I’m an outsider on the situation, perhaps it’d be better to let someone with a more intimate feel for this stuff break it down for you.

“The Winter Meetings are akin to weather report,” Scott Boras explained Wednesday from Orlando. “We had the (Shohei) Ohtani solar eclipse. There was a darkness in the industry for almost 10-12 days where everyone was involved. That is a pretty rare event in baseball when everyone is involved. That set back a lot of normal winter activity.

“And then we’ve had kind of the Miami rain, where we’ve seen a heavy liquidation and such that we’ve had clubs really trying to define on a number of levels, something very irregular,” the super-agent-cum-weatherman continued. “We’ve seen one of our major league jewelry stores become a pawn shop, and a lot of teams were wrapped up in evaluating those assets. So now we’re starting to get through the trade haze and fog, which is clearly something that is usually taken care of in November, which is being addressed now.”

What the what?

I guess we could say there’s been a cold front blowing in as teams put Jake Arrieta, Yu Darvish, J.D. Martinez et al. on the back burner to focus on trading for lower-cost options. Things will eventually come around and you’ll see teams finally make it rain with nine-figure contracts, it’s just that they want to explore all the other options before writing those extra zeroes.

But until such time as that happens, let’s all sit back and marvel for a while at the fact that Tyler Flippin’ Chatwood’s run as this free agency period’s richest contract has lasted so long.