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Is Jon Gray’s Price Tag Going to Be Surprisingly Reasonable? If So, Shouldn’t the Cubs Make Him a Target?

Chicago Cubs

Impending free agent Jon Gray is definitely the *type* of free agent I’m hoping the Cubs aggressively target. Setting aside the particulars of his situation for a moment, what he represents is a (1) high-upside (2) admittedly high-risk (3) shorter-term (4) type at a strong position of need for the Cubs. At a minimum, that’s where the Cubs should make use of their considerable financial resources this offseason – if it takes a higher average annual value to get these guys to sign on a shorter-term deal, then so be it.

You get enough of those moves right, and you might find yourself competing in 2022-23 without any kind of risky exposure in 2024 and beyond when more prospect waves are arriving. The Cubs have tons and tons of available short-term dollars … use them!

As for Gray, specifically, we’ve discussed him before but there’s a reason to bring him up again today. Patrick Saunders at the Denver Post reveals that the Colorado Rockies tried to extend Gray before the offseason arrived, which in turn includes quite a reveal about the range of contract Gray might want:

 The Rockies made a contract offer to right-hander Jon Gray before the end of the season, hoping he might accept it before becoming a free agent. The offer was rejected, but that doesn’t mean Gray won’t re-sign with Colorado. His desire to remain with the Rockies is genuine, but he owes it to himself to explore the market, and, perhaps, have some leverage for a better deal with Colorado.

Gray, who made $6 million in 2021, is likely seeking a three- or four-year deal at about $9 million-$10 million a season. For comparison’s sake, the Rockies recently gave right-hander Antonio Senzatela a five-year contract extension worth $50.5 million.

There is a surprising amount to unpack there!

1. For one thing, Gray at three or four years and $9 to $10 million AAV … well that’s mighty interesting. It’s not quite “short-term,” but it’s short-ish term, and the AAV is actually on the lower end of what I would’ve thought. (The whole “short-term, high-AAV” signing thing should not be thought of as something having rock hard edges (“No more than two years, no less than $15M AAV, sir!” … you have be more flexible than that …. )

2. For another thing, if that’s the range Gray is looking for, the implication is that the Rockies’ offer was for considerably less. What does that say about how they value Gray, and you do always have to be modestly cautious when the org that knows a player best is much lower on him than you would’ve thought.

3. For still another thing, if that’s the range we’re talking about the Rockies NOT being willing to go to, then you can tentatively rule out Gray receiving a surprising Qualifying Offer (which he would probably accept, and even if not, is Gray a guy you’re willing to give up a high second rounder and draft bonus pool space AND IFA bonus pool space to sign?). If Gray does not get a Qualifying Offer, he becomes all the more attractive as the type of short-term signing the Cubs should go after.

Let’s say Gray doesn’t get a qualifying offer, and let’s say he really is just looking for, like, a 3/$30M deal. Cool, cool. But is he ACTUALLY a guy the Cubs should go after at that level?

Gray is a really tough one to evaluate because of extremes in his performance and the Coors Field thing, and that is perhaps what makes him compelling. If you’re RIGHT about him, you could land yourself a stud on a reasonable deal. If you’re WRONG about him, you could wind up in a Tyler Chatwood situation – you know, the last time the Cubs aggressively targeted a young-ish former Rockies pitcher with tons of risk and tons of upside.

Which is not necessarily to compare those two as pitchers, only the situations.

Gray, who turns 30 next month, is a former top three draft pick who has dealt with minor bumps and bruises throughout his time in Colorado while mixing exceptional performances with disappointing ones. Unlike most Rockies players, he actually doesn’t feature enormous home/road splits, and the bones are all there for a mid-rotation starter. He throws 95 mph, has a top-tier slider, and also throws a curveball and a changeup. He had a really down 2020 season, but it’s pretty easy to throw that one out as a pandemic one-off, because he bounced back well in 2021.

Of course, “well” for Gray has generally been around a league average ERA or slightly better (last season’s ERA, when adjusted for the home park, was about 4% better than league average). He’s never quite lived up to his draft pedigree.

(via FanGraphs)

With Gray, you’d have to be pretty confident that you could either unlock another level in his game, or at least bring up the floor. That’d take some digging – more sophisticated than I’ll get into today – but a couple really superficial places I’d look quickly: (1) His performance takes a big hit with runners on base (specifically, his strikeout rate goes way down); (2) Why does he give up so many line drives (specifically), and how did he cut that number (again, specifically) in 2021?; (3) The fastball has been a pretty poor pitch for him overall, but he throws it 50% of the time – how necessary is it to make the nasty slider work, and could that balance at least be adjusted a bit?; (4) As a third pitch, the changeup appears to be wildly unsuccessful (compared to the curveball), so why has he started throwing the changeup more than the curveball the last few years?

On the balance, I’m intrigued. And I’m all the more intrigued thinking about whether you could actually get Gray on a three-year, $30 million deal. That seems like a surprisingly LOW risk bet for a guy with the upside of a 3.0 or 4.0-win mid-rotation starter. I would expect him to do better, actually. Maybe much better. But if that’s the rough range, count me in on the Cubs aggressively pursuing him for one of their many, many rotation vacancies. They need to get a lot of guys this offseason, and I’d rather they took chances on guys like Gray, who come with upside (and over three years, even better), but who also won’t kill their efforts over the next few years if they don’t produce. Short-term, high-risk, high-upside, high-AAV types (and, in Gray’s case, you can apparently play around a bit with the short-term part and the high-AAV part … ).

I suspect we’ll be talking more about Gray soon.

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.