Somehow, We Still Need to Keep Talking About Blake Snell and Jordan Montgomery

This was all just this side of cute, until about the beginning of February. It still hasn't definitively worked, because Scott Boras has convinced the first three of his high-profile clients to sign this winter to do so on deals that give them opt-outs after every season. Still, we're at the point where it's inarguably troubling to see the same old playbook being run. The owners are trying to corner the players union, and soften the ground for themselves ahead of the next CBA negotiation fight. As a result, they've dug in their heels, and (as it very often is) it's two starting pitchers who are left somewhat out in the cold.

Jordan Montgomery is far less likely to be amenable to signing a short-term, opt-out-laden contract than were Cody Bellinger, Matt Chapman, or Rhys Hoskins. Unlike Bellinger and Chapman, he was traded this season and wasn't offered a qualifying offer, and that means he could have one attached to him next winter if he wanders back out into the marketplace. Unlike Chapman and Hoskins, he's coming off one of the best seasons of his career, and can't feel especially confident of being able to go back out there next winter and make any more than this.

Some of the same goes for Snell. He does have that qualifying offer hanging around his neck this winter, but he's also coming off his second Cy Young Award in the last six seasons. It would be very difficult for him to raise his stock much from here, and easy to have it sag significantly. 

For their part, teams aren't likely to like the idea of signing Snell or Montgomery to a Bellinger- or Chapman-type deal, anyway, because those contracts operate very differently for pitchers than for hitters. Carlos Rodón is the illustrative case. He signed a two-year deal worth $44 million with the Giants prior to 2022, but it included the right to opt out of the second, slightly richer season of the pact. At the trade deadline that year, the deal became a poisoned pill. Teams were too afraid that Rodón would get hurt and forego his opt-out, becoming $22.5 million in dead money on their books the following winter, to trade for him, and (since he didn't ultimately get hurt) the Giants lost him via free agency after that season.

Snell and Montgomery are both healthier and more established than Rodón was when he signed that contract with San Francisco, too, so they'd have to get something closer to $60 million over two years (or, like Bellinger, $80 million over three) to sign on to such a deal. That's going to be a tough sell on both sides, for all the reasons enumerated above.

It's fairly blatant market manipulation. It's in bad faith. In a slightly more just society, the union would be able to make a case to the National Labor Relations Board and get the owners sanctioned for this repeated behavior, which you can also spot in the offseasons entering 2013, 2014, and 2019, always with a dual goal:

1. Put pressure on agents and union leadership by frustrating players and withholding a greater share of their revenues, to establish leverage for the coming negotiations; and
2. Create a false anchor that can then be phonily pulled up in the final offseason before the actual negotiations. This move--giving richer deals right in the shadow (on either side, chronologically) of CBA deals, fighting tooth-and-nail for the last dollar in the years furthest from them--is designed to put the players on the wrong side of public opinion, once conflict (a conflict the owners are inviting, even fabricating) does burble up.

Alas, we don't live in that kind of world. So, let's briefly consider a more creative structure of contract for Snell and Montgomery, and ask ourselves whether the Cubs (hardly overcome with great options at the back end of the rotation) are in position to offer them.

Instead of a straight opt-out deal, and instead of a traditional long-term deal (which both pitchers deserve, but which sure doesn't seem to be coming at this point), the best solution available to all involved is probably some version of what Boras once dubbed the "swell-opt". In short, these would be deals similar to Bellinger's and Chapman's, but the salaries would be frontloaded, and the team would have the right to void the hurler's opt-out clause by exercising a large, multi-year option instead.

To take that from abstract to concrete, let's talk about Snell. He's the one who would give the Cubs rotation a truly different and level-changing new dynamic, but he'd cost a pretty penny. The Cubs could, plausibly, offer a three-year, $67-million deal to the two-time Cy Young winner, but $31 million of that would be paid in 2024. Then, Snell could choose to stick around for $20 million in 2025, or opt out, with the Cubs getting a chance to exercise a five-year, $150-million deal in order to prevent that. After 2025, Snell would also have the right to opt out, or else claim $16 million for 2026. The Cubs could void his opt-out by exercising a four-year, $100-million option for 2026-29.

The structure would be different for Montgomery, who is older and doesn't have the QO attached to him this winter, but that's the general idea. It's a deal that includes some substantial risk on both sides, but there's also tremendous upside for both parties. At this point in the spring, it's something Boras should be open to. The Cubs should be willing to simply pay either Montgomery or Snell upward of $150 million for five or six years, but since they clearly aren't (and have the backing of a collusive market in that respect), this is the kind of happy medium place where they could meet Boras.

According to Baseball Prospectus, the Cubs' offense is just fine. The PECOTA system projects them for a 102 DRC+, meaning the offense is above-average, as-is. They fall short because they're also projected for a 102 DRA-, meaning the pitching staff is almost exactly as below-average as the hitters are above that line. Montgomery and Snell are the remaining ways they could address that before the season begins. This kind of deal is how that would, in all likelihood, need to look.

What do you think of this contract structure as a compromise between the Cubs and the top remaining free agent arms? Do you view the owners' behavior as legitimate? Sound off below.