I'm not getting any closer to answering how much more a superstar should be valued, but the solution has to do with playing time and a chaining effect.

You get a 6 WAR player, and he's going to play as often as he's capable of getting into the lineup. For players of lessor ability, this is not the case. I brought up the 0.25 win player earlier, lets call him RobbQ. RobbQ is not good enough to play everyday, but just good enough to stay on a roster. So in his bits of playing time, he actually only gives you .05 or .10 WAR.

I agree with AROM.

WAR = playing Time * (Talent over baseline)

playing Time itself is a function of Talent over baseline (plus management stubborness).

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I'm trying to have a basis for discussion by coming up with specific scenarios (as drdr did) and then forcing people to come up with a dollar valuation under those specific scenarios. (If the scenario is not specific enough, then make it more specific.)

Please don't come up with reasons as to why we can't have a discussion!

Unless someone wants to come up with a plausible scenario where 2 3WAR players are not going to get paid anything close to 1 6WAR player (or 2 2WAR players compared to 1 4WAR player, if you object to the scarcity of 6WAR players), then I'm going to continue to maintain that the status quo is that the 2-for-1 makes nary a difference.

As I said in my scenarios, if you pay 1 6 WAR player exactly as much as 2 3 WAR players, you are still better off with 6 WAR + 0 WAR if you are in playoff contention, about equal if you have no chance for playoffs (unless you count on the 6 WAR player to be the first piece of the championship 3 - 5 years down the line) and 6 WAR player is actually worth less for huge favourite (because if 1 3 WAR player gets injured, you are still a favourite, but if 1 6 WAR player gets injured, you are back in the pack).
As far as paying goes, if you are paying free agents, I think that past practice has shown that clever organizations shopping for 3 WAR players would pay them between 80% and 100% of their projected win value, maybe less for teams whose marginal win value is high. But 5+ WAR players will almost always get full 100% value from the team that signs them, maybe even a few percents more. Since they are mostly signed by teams with higher marginal win value, they will be payed more per win.
To put another price on value: if we accept that Hanley is 6 WAR player, Lowrie and Lester are 3 WAR players and that Lowrie and Lester (together) will be payed over the next 6 years roughly the same as Hanley (and all of them keep exactly the same value over the next 6 years - all of them are young enough), Boston should trade the two of them and some prospects - let's say two who are pretty good bet to be 2 - 3 WAR players for a bulk of their careers or one with upside for 5+ WAR, but with low probability of achieving it (more like that CF kid they traded for Gagne than Hanley when they traded him) and some classic fillers (classic good arm/no control or good tools/no results guys). Because they could then get Lowe and be about 3 wins better than they are now and in Yankees - Rays - Red Sox division that last win in 90+ range that gives you playoffs has really big value.

It's spelled Chone, but it's pronounced "Throat Warbler Mangrove"

Thank you. Now a story about Arthur "Two Sheds" Jackson.

then put a price tag on these guys.

Does this really matter? Didn't the Yankees completely destroy this idea?

Another thing, paying for true stars is always a good thing. A-Rod's first contract was good, even Giambi's contract was good, Mussina's contract was good, Bond's and Unit's contracts were steals, Madux's contract was steal... Very few big contracts for true superstars were failures, even Jeter's contract wasn't too bad from Yankee perspective. So overpaying superstars by 10% or so is not a bad idea if you can count on their production.

For Giambi's contract, I should've said relatively good from NYY perspective and their higher marginal win value.

Another thing, paying for true stars is always a good thing. A-Rod's first contract was good, even Giambi's contract was good, Mussina's contract was good, Bond's and Unit's contracts were steals, Madux's contract was steal... Very few big contracts for true superstars were failures, even Jeter's contract wasn't too bad from Yankee perspective. So overpaying superstars by 10% or so is not a bad idea if you can count on their production.

I agree with this idea.

If Brown hadn't had that parasite in 2004, the way he pitched at the beginning of that season, even his contract would have been net positive.

The most disastrous contracts are those for 2-3 WAR players who have potential (or had potential) to reach 5+ WAR and who are paid 80% of what 5+ WAR players are paid. That includes players who can be stars when healthy, but can't be healthy, like Nick Johnson, and superstars who already are in decline.

Good night and happy New Year.

Another thing, paying for true stars is always a good thing. A-Rod's first contract was good, even Giambi's contract was good, Mussina's contract was good, Bond's and Unit's contracts were steals, Madux's contract was steal... Very few big contracts for true superstars were failures, even Jeter's contract wasn't too bad from Yankee perspective. So overpaying superstars by 10% or so is not a bad idea if you can count on their production.

This argument is circular. You're defining "true superstar" after the fact, by what happens during the contract. Paying for players who overperform is tautologically a good thing, but you don't know who's going to overperform until after the fact.

Mike Hampton sure looked like a true superstar at the time of his big payday, and if he had pitched 1500 innings of 3.00 ERA, that would have been a steal. Conversely, if Bonds had Griffeyed or Jeter had Canoed, they'd be a colossal albatross.

Disagree. Hampton and Neagle weren't really true superstars. Neither was Zito.

Ken Griffey would seem to be the one counter-example. At the time of the signing, he was 30 and one of the five best players in baseball. He proceeded to get hurt in 2001 and stay hurt for most of the remainder of his contract, only returning after injuries had robbed him of his defensive abilities.

Certainly, any contract can be a bad one if the player gets hurt. But if injury, rather than descent into suckitude, is the primary problem with these superstar contracts, that's a good reason to spend your money on superstars.

I think Bill James said in one of the Abstracts that this is why it's a good idea to sign Dave Winfield - even if he has an off year, he's still Dave Winfield, and he pushes you toward a pennant. If Ed Whitson has an off year, your team gets worse.

Manny Ramirez would be another one for the sign-superstars argument.

On Tango's issue, the best case for valuing a 6 WAR player over 2 3-WAR players is that the 6-WAR player gives a team more ways to build a championship team. Let's say the goal of the Red Sox is to assemble a 95-win true talent team, so they will virtually always make the post-season. So they need 14 wins above average. That's almost 1 WAA per regular player, which is what your 3 WAR players give you. It's very hard, if not impossible, to be above average at every position (and 5 starters). Even a good farm system will not produce adequate players at certain positions for years at a time; the FA market will not always have players who meet your current needs. The market for baseball talent is not that liquid -- there's no Amazonbaseball.com where I can just order a 3-WAR shortstop and have him arrive in time for spring training. With a 4 WAA (6 WAR) player under contract, a team can carry a couple of average players, or sustain an injury, and still reach its goal. So for a rich and ambitious team, it makes a lot of sense to sign elite players.

That said, I think Tango is right that in practice, MLB salaries are linear, and teams don't pay elite players more per win. Or the premium is small enough that it hardly matters. My guess is this is a function of injury risk: the downside of tying up so much payroll and talent in one fragile human is substantial. The odds that 2 3-WAR players will both sustain career-ending injuries is much smaller than the risk for 1 6-WAR player. In fact, if we knew how much teams paid to insure the elite players, and included that in their salary, we might find that teams do effectively pay proportionately more for their services.

Bump (I'm interested in what people have to say about Tango's question.)

I'd think 6 > 3+3, myself - in part because the replacement level is not fixed - our assumptions for it assume a value that is, I think, on the low end. If the replacement level is actually a half win higher, then we're comparing 5.5 to 2.5+2.5 (and so on).