What would a Justin Steele contract extension look like?

The Cubs seem behind the modern baseball curve of signing young, talented players to contract extensions. This is one reason the World Series core was all traded and it’s a reason why Ian Happ is going into his walk year.

I’ve written here about what a contract extension for Ian Happ might look like and what one for Nico Hoerner might entail.

But what about pitching? The Cubs have focused on drafting pitchers in recent years, so coming up soon might be a time where they will have to think about locking up young pitching talent for the long term. Of course, pitchers can have more dicey injury futures than position players, perhaps one reason we don’t see many such deals.

Justin Steele, who had a breakout year in 2022, especially over his last 10 starts (1.49 ERA, 1.233 WHIP, 65 strikeouts in 54⅓ innings), could be a candidate for such an extension.

I looked around to see what sorts of comparable pitchers I could find who received long-term deals within the last year. I found two.

The Braves gave Spencer Strider a six-year, $75 million deal just after the season ended that could be a seven-year, $97 million contract if an option is exercised.

Now, as good as Steele appears to be, Strider is (at least at this moment) a better pitcher. He had a better 2022 season and finished second in NL Rookie of the Year voting. The Cubs aren’t going to pay Justin Steele that much, nor should they.

Here is perhaps a better comp. The Brewers, last summer, signed Aaron Ashby to a five-year, $20.5 million contract that could be a seven-year, $46 million contract if a pair of team options are exercised.

That’s the sort of deal I think the Cubs could do for Steele, who isn’t arbitration-eligible until 2024. Steele, in fact, had a better year than Ashby did in 2022 — Ashby posted negative bWAR for the Brewers, while Steele’s 2022 season was worth a solid 2.0 bWAR even though he suffered a back injury in late August and made just 24 starts.

So that’s what I would propose — a deal like Ashby’s. His deal calls for the following (and also a $1 million signing bonus):

2023: $1 million
2024: $1.25 million
2025: $3.25 million
2026: $5.5 million
2027: $7.5 million
2028: $9 million (team option)
2029: $11 million (team option)

Steele is almost three years older than Ashby, though this year will be his age-27 season since he doesn’t turn 27 until July, while this is Ashby’s age-25 season. Both are lefthanded; they seem quite similar types of pitchers.

The thing is, Jed Hoyer’s front office doesn’t seem interested in paying this sort of money up front, which could save them money later on. I just don’t understand it.

Is there risk in signing a pitcher to a deal like this? Of course there is. But if Steele is the sort of pitcher we all hope he can be, this could be a bargain.

Who says no?