Given recent contracts given out to young players (Sizemore, Granderson, Tulowitzki, CYoung, and most recently Longoria), and given contracts given to superstar players before they become free agents (Pujols, MCabrera), my question for you is: when do you approach Upton's camp for a long term deal, and how much money over how many years do you offer if you're Josh Byrnes?

If I and my coaches and manager and scouts and whoever think Upton is the future stud everyone seems to think, then I'd happily give him Longoria's deal (depending on Upton's D). The power he's shown so far this year (ISO>250) is amazing for such a young player.

My qualms:

1. Assuming I still have faith in Chris Young (is he signed long-term?), Upton's future is as a RF. Being a stud RF is hard, you need to be putting up OPS+s around the 130 range. I'd take some convincing that's his future ... maybe not a lot but some.

2. You know this is coming. He's K'ing about 1 per 4 AB. You simply can't maintain that kind of BA (345 this year) when you do that. His on-contact numbers this season are 455/788 and that BA is not sustainable (and that's probably not, yet, his true talent for power on-contact either). What is it with these Uptons and their crazy on-contact BA numbers (BJ was 444 last year, a more believable but really good 385 this season)?

2a. Obviously he's young and that K-rate (which isn't awful) could improve. The point of 2 is that, at the moment, I'm thinking a BA of 280 is closer to what we can expect. He hasn't shown any walks yet (though that will increase if he keeps up that ISO) but, even with that ISO, you could be looking at a long-term line like 280/330/530 -- damn nice but hardly spectacular for a RF. So it really is a question of how much you think he will improve from here. If his K-rate and walk-rate improve, he's prime Cesar Cedeno (adjusted for era) and you sign him immediately if you can. If he doesn't, maybe Alfonso Soriano's career line (280/330/520 ... go figure) which would be average-ish for a RF. His downside would seem to be Joe Carter or Jeff Francoeur (who has greatly improved his K-rate so far this season) if the power isn't quite for real.

Anyway, barring major injury, I have very little doubt that Upton will be a starter for the DBacks for at least the next 5-6 years. Given that, he'll certainly make at least $18 M over his 3 arb years ... or it might be $24 by the time he gets to arb. Take a little discount for that injury/collapse risk and I'll buy those babies out. If he wants to give me some bargain FA years too or some higher-priced options on those years, I'll almost certainly bite. And, like I said, if I and my advisors were sufficiently confident that Cedeno is his future, I'll definitely try to buy out this year and 7 more.

And he should be thrilled with a deal like that. He'd have a nice guaranteed chunk of money and still be an FA following his age 27 season. Wow!

Chances are Justin Upton will be an extremely rich man.

I'm also curious as to what all these buyouts mean for the high-payroll teams who are more reliant on FAs (Yanks, Cubs, Red Sox, etc.)? If these small-medium market teams can buy out their young stars through age 30-32 and they sensibly manage their budgets (i.e. don't end up with contracts they need to dump), the FA market from 2012 onwards is gonna be slim pickings.

Of course, young players and arb years have always been the biggest market inefficiency in the game (and it is a real market inefficiency). Teams have always recognized that, but some of these long-term deals have the potential to be hugely profitable to the teams. I think we might be seeing a real shift -- long-term "budget" deals with young players, declining interest (and salaries) for older FAs -- and the Union is going to have to do something, especially if revenues keep expanding.

Wouldn't the teams just put the money they save not signing FAs into locking up their young players? I'm not sure this mechanism would decrease the % of revenues spent on salary - it could lead to higher payrolls for small- and mid-market teams as it decreases it for large-market teams. The corresponding transfer of wins from large to small markets would drive a revenue transfer, and overall it could just mean greater parity on and off the field.

I'm having intuitive problems with my own argument though, since it's hard to imagine, say, Cincinnati and Miami becoming so baseball-mad as to make up for losses in New York. Perhaps the total revenues would drop even if the % paid as salary didn't, which wouldn't be a good thing for baseball.

On a not-quite-related note, wouldn't the scarcity of free agents drive the price back up for the mediocre ones?