At what point do you sign McLean...

[roger_that]

...or Tong or whoever to a long-term contract buying out his Free Agency years?

I'm using McLean as an example but really I'm talking about any successful player under contract at any point in his first six years. We're going through the late stages of this discussion with Alonso right now, and it's been a matter of some dispute whether the Mets should have offered him a lucrative contract towards the end (or middle?) of his first six years and whether he (meaning him and Boras) should have bit or passed on the deal.

It's a philosophical question, and a financial one, all at once. For the Mets to offer McLean an eight-year deal right now, after three phenomenal starts, seems an absurd gamble on their part that he will continue to pitch as he has but a very good one for him to accept, if it were offered. I'm talking about a lot of money that they need not gamble with before they have more evidence of his superior pitching, so it's a silly discussion at this stage--but when do you think it slides into the "not silly" category? After a year of excellent pitching, when they have control of him for another five years? After three years of excellent pitching?

By his fifth year, I think his agent will say, "No, we're close enough to free agency that I want to risk living with an arbitrated salary for another year and then test the FA market."

So there's a sweet spot when both the club and the player are willing to gamble on a lucrative extension. My question is where do you think that sweet spot is?

Answering "It differs for every player" is just evasive. Of course it differs for every player,and every agent, and every club, but I think you can generalize about a young player who performs very well, and your inclinations to offer that lucrative contract at a point when he's open to signing it. In fact, I think I'll make a poll out of this--it will help me to focus on what my answer is to this question.

[MFS62]

I voted for after two excellent seasons. For any rookie, you want to be sure they can survive after the proverbial sophomore jinx. (the adjustment, re- adjustment and adjustment to the re-adjustment, etc.)

Later

Edited August 28, 2025 by MFS62

[Fman99]

I voted for after two excellent seasons. For any rookie, you want to be sure they can survive after the proverbial sophomore jinx. (the adjustment, re- adjustment and adjustment to the re-adjustment)

Later

 

This makes sense to me - we've seen Alvarez and Vientos both struggle to put together successful seasons consecutively (though Vientos is finally making his case in August).

[roger_that]

It's the sophomore jinx really a thing? I don't mean "has anyone ever had a worse second season than his first season?" The answer to that is "of course"-- but players often have worse fifth seasons than their fourth season. All players fluctuate. No one ever has had a career of continually improving seasons or continually declining seasons. It's just more noticable when someone has had only two seasons

And your example of someone with a declining second season, Vientos, isn't even certain yet. If he stays hot for the next month, there may not be any difference, other than his injury this year, to Mark where he's had a better 2024 than 2025.

Should the Mets offer Vientos an eight year deal after this season if he stays hot?

[MFS62]

Only superstars get an 8 year deal. And that is based on how team management views him. So that would be off the table for him. He's not at that point yet.

But if he stays this hot for the rest of the year, and at his age, a four or five year deal is certainly a possibility for Vientos.

Later

[Cowtipper]

How many times have we seen prospects on other teams dupe a team into signing them into long term deals, just to have those deals fall flat on their faces? Jon Singleton, Evan White, Scott Kingery. MacLean's hot start reminds me of Christian Scott, who performed well in five of his first six starts. Where is he now?

[roger_that]

Where is he now?

On the IL, I think.

So where in McLean's career would you sign him to contract extending into his free-agency years? "Never" is certainly a respectable choice, one I might just take myself, especially with a pitcher. But is there no sweet spot where a good young player acquires a modicum of security and the club acquires his services for a reasonable cost?

[Benjamin Grimm]

Give him a four- or five-year contract when he's two years from free agency.

I hate opt-outs, by the way. As a fan, they just confuse everything. But I suppose they're here to stay.

[stevejrogers]

Better hope he doesn’t have a Boras-like agent who will take their client to free agency, no matter what!

[Edgy MD]

They all have Boras-type agents.

[kcmets]

Sign him tomorrow! This way when his arm falls off in September

he'll have some extra walking-around money.

[Gwreck]

I hate opt-outs, by the way. As a fan, they just confuse everything. But I suppose they're here to stay.

 

I’ve wondered why the change in terminology was embraced such that they are now more frequently called “opt-outs” rather than “player options.”

[Edgy MD]

I take the distinction as a player option being the option to accept a single additional year at the end of a contract, and an opt-out being a choice to exit in the middle of a long-term contract, forfeiting multiple years for another shot at the marketplace.

[roger_that]

Aren't opt-outs a mere complication to an already-complex problem? They seem to present a way to mitigate or compromise the difference between a club's proposal and an agent's acceptance of that proposal. Are we suggesting that without an optout there is no ideal point at which to offer a young player a contract extending into his free-agent years?

The key question to ask here is how prolifigate a club is, and how little wasting many millions of dollars matters to that club. But since we're talking about the Mets specifically, we can tailor the question to their finances, which seem to accept 'wasting millions of dollars" as the cost of doing business. I suppose the answer does depend a lot on the club offering the contract.

With so many potential young stars on their roster, this issue should arise several times in the near future. The Mets can lock down the peaks of numerous young stars, so it will be interesting to see what their philosophy on this question is. High-risk? Moderate? I don't think they'll be playing it very safe, which is to let stars in their 20s enter free agency very often.

[Frayed Knot]

Let's go back to ARod's original deal with Texas: 10 years at around $25/per with an opt-out after year seven and at a time when opt-outs were new to the process.

When the deal was signed it not only topped anyone else in baseball on a per/yr basis but was way ahead. I don't think anyone else was making even $20/per at the time. And for the first five years or so that gulf remained to the point where I seem to recall teams being even more restrictive with what they'd offer than they were back when his deal was new. After year three, of course, he was dealt to the Yanx with Texas playing a significant portion of the remainder -- some $75 mil IIRC or about three years worth of the remaining seven -- so neither the team that had him nor the one getting him wanted to have that per/year rate on their books going forward.

But by year seven the market pendulum started to swing the other way which is why Boras/Rodriguez wanted that clause in there in the first place. Not that they could anticipate exactly when/if the original deal would stop being such an outlier but it's always likely that it will at some point and, as it turned out, they pretty accurately nailed the timing. You'll also recall that Rod did opt to opt-out and did so right in the middle of an ongoing World Series so he could suck all the air out of it just as Steinbrenner used to do with managerial firings if his team wasn't involved in October baseball.

I think, left to his own devices, Cashman would have let Rodriguez walk but Hank Steinbrenner, the since-deceased older brother, probably heard George's voice in his head and tacked on a large extension (a completely new contract really) that took ARod to age 41 or so, a new marriage which wound up ending in a very ugly fashion.

So, anyway, that's the point of opt-outs from a player's view: if the market doesn't rise you get top salary AND the security of a long-term deal. And if it DOES rise you get to become a FA again at a time when the old ceiling is no longer the ceiling and when you're X number of years younger than you would be when the original deal was due to end.

[roger_that]

So the opt out is basically the club's concession to the player "ok, we'll take the hit if you're still performing at a very high level in year X and if you suck eggs at that point, we'll keep paying you top dollar anyway"? Presumably, this is an incentive to sign the contract for less than the agent is asking for.

[ashie62]

The Roman Anthony's Jackson Chourio Colt Keith of the world and many more are getting 8 years for about 130m

Sign McLean to something similar

[roger_that]

The Roman Anthony's Jackson Chourio Colt Keith of the world and many more are getting 8 years for about 130m

Sign McLean to something similar

 

That's certainly one way to go.

Can any club afford to do that (or something very similar) with their top-dozen good young players? Or do you want to pick your spots?

Is it equally wise to do that with pitchers as with hitters?

Is it an advantageous policy for both players and clubs? This one seems easy--it's a no-brainer for players, who get guaranteed more money than they've ever seen even if they break both legs tomorrow. But consider Tom Seaver, who got traded because he demanded a long-term guaranteed contract at top dollar, except the amount he was demanding turned out to be pretty piddling in retrospect because players' salaries kept breaking records and Seaver remained a good pitcher for years afterward. In other words (as I recall) Seaver was asking for the moon (in 1970s dollars) but it would have turned out pretty good for the Mets if he'd simply gotten the money he was asking for (in 1980s dollars). I could be misremembering here--correct me if you think I'm wrong--but the principle of "Be careful what you want because you just might get it" seems to be applicable. Still, it's hard to fault someone for being greedy and accepting an 8-year deal that makes him wealthy in advance of sustained MLB success.