Reading over the last couple pages I have my money on the guess made by
chrisfont9:
4 this year, tenish next year, 25-30 per year for the following 5 years.
From a traditional contract perspective this scaling makes sense, but IMO it makes more sense from a baseball standpoint to do the opposite. Give him a big payday upfront and frontload the contract as teh team is likely to have fewer cash obligations in the next couple years. As the contract ages, our young core will likely be hitting arb (or better yet, be great and getting extended), thus increasing their salaries either way. So from a cash-flow perspective, spending more up front makes sense. It also has the added value of making Crochet MUCH more tradable in the back end of the deal, as AAV recalculates based on the remaining contract. It's also more attractive for Crochet, so he might accept a lower total $$ amount if the contract is front loaded. Unless there is some rule prohibiting this contract structure, I'm surprised more teams aren't going this way.
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Personally, I'm optimistic that an extension gets done. In all of baseball I think extending young pitching is probably the place where player and ownership interests are most aligned.
The way I see it, signing FA position players is like playing craps or blackjack. You probably lose on value, but over a decent sample size your results are relatively predictable and you're probably not losing a ton if you do a good job of it. FA pitchers are more like playing slots. You might hit a jackpot on a low investment and get a ton of value (see: Lance Lynn), but on the whole you're losing more consistently and with a LOT more variance.
The reason for this is that the driving force behind position player attrition is skills attrition with injury as a secondary factor, while with pitchers it's the opposite. While some position players careers are derailed by injury, it doesn't happen nearly as often as it does for pitchers. Skills attrition also affects players in a way that is more commensurate with their actual ability. If you're barely good enough, it doesn't take much to fall down to replacement level. Meanwhile, players that excel in multiple dimensions of the game are going to be able to maintain a useful amount of value over time more consistently, even if they do still fall off.
Meanwhile, elbow ligaments have no respect for talent. Certain pitchers may be more injury prone due to particularly violent mechanics, but the baseline is very scary.
Given the impact of the luxury tax (even if only on IFA money and draft picks, let alone payroll), large contracts for pitchers are much riskier and can have nasty downstream effects in the downside case, and the downside case is a lot more common than with position players. A middle to big market team can absorb a bricked 15-20mm AAV contract much more easily than a 30-40mm AAV contract. So even if the team assumes more risk by extending a young pitcher, the impact of that risk is mitigated by the overall smaller outlay of cash in a way that is much more impactful than for position players, where the risk mitigation is less important.
For players, the same dynamic plays to the player's interests. Young, talented pitchers are much more likely to lose their career to injury than young, talented position players. Having a more moderate contract locked in still guarantees generational wealth, compared with the very real risk of wholly missing the boat. A career-ending injury for a pre arb or even early arb player is absolutely devastating. It's not just the opportunity cost of losing a huge payday but the reality of facing a massive career change in one's early to mid twenties (without the education to back it up for many). For a position player, betting on oneself to make it through 3-4 years to get to free agency is like betting on oneself at the poker table. For a pitcher it's pulling the arm on a slot machine.
So in the end, both sides have a tremendous incentive to mitigate risk, and contract extensions achieve that for both sides.
Addendum -- I'm less confident in this bit, but I'll put it out there anyway: I think the prospects for older pitchers are also better than for position players. The aging curve hits everyone, but it seems like there are more pitchers that can sustain a high level of effectiveness as they age IF they manage to avoid or effectively recover from injuries. These guys may not be able to secure a megadeal in their mid 30s, but they
can lock down 1-3 year contracts with big AAV in part for the same reasons why exensions make sense. A short term signing, even at high AAV, isn't likely to cripple your francise's future if it bricks. For a position player signing a big extension that has you hitting FA in your mid 30's is very likely to be your last really good contract. For a pitcher though, it's easier to imagine a path where you exit your contract extension and then string together a few seasons of big money to close out your career.
