Chuck Finder nails it here:
True, words are cheap. Star contracts are expensive. And that, wacky as it seems, would probably be a more tell-tale day for long-suffering Pirates fans: Not the moment when the club noses above .500, but when the owner locks up core players to long-term, marquee deals. . . and keeps them around on that growing payroll.
Yep, that probably is going to be the moment for a lot of people, if it ever happens. And that will be a relevant moment. Of course, if the Pirates do get there in the next few years, 95% of the work will already have been done. The players fans will want to lock up will be contributing peak seasons at relatively cheap prices, and fans will want to keep them in Pirate uniforms for their decline years. And few will mention that the failure to give out "long-term, marquee deals" has been about 99th on the list of the Pirates' problems over the past decade or so.
The Aramis Ramirez giveaway was a travesty, and nothing any fan wants to have happen again. But the Bucs have paid to control free agency seasons by Brian Giles (great contract), Jason Kendall (a disaster), Ian Snell (bad idea), Jack Wilson (largely irrelevant), Freddy Sanchez (irrelevant), Paul Maholm, and Ryan Doumit. Except with Ramirez--which was, again, a debacle--the Pirates' problem has not been an unwillingness to pony up for free agency seasons, or to keep their core players around more generally. The problem has been the fact that most of their core players weren't very good to begin with, and were even worse by the time they amassed six years of major league service, which is the point after which a player becomes eligible for free agency.
Most players have passed their peak by the time they finish their sixth year. And if the Pirates' willingness to keep stars around on long-term deals is to be some kind of litmus test--and it probably will--then you can look at someone like Pedro Alvarez even now and see how he might become a problem. Now, I realize that sounds absurd, but: Alvarez isn't exactly slow, but you can watch video of Alvarez running and see how he might become a bit of a slug as he gets older and adds a few pounds. His defensive issues at third are well documented, and he probably won't be playing there in six years. He has issues with strikeouts that could get worse if his bat slows down a bit, as well.
My point is not to write an obituary for Alvarez's career before it even starts. He's a great prospect. And with Scott Boras as his agent, he'd be very unlikely to sign an extension with the Bucs in the first place. My point is that Alvarez is pretty likely to do the most damage in the years in which the Pirates already control him, during which he'll be pretty cheap. And after that, it may well turn out to be in the Pirates' best interest to let him go. Assuming the Pirates keep Alvarez in the minors to start the year, they'll have him year-to-year through 2016, after which he'll be almost 30. I would not bet on Alvarez being a great player into his 30s.
Someone like Andrew McCutchen, who is an excellent athlete with a very well-rounded game, may well be a different story, and is probably exactly the sort of player the Pirates should at some point consider locking up long-term. If he continues to develop in the next two years or so, he's an outstanding bet to continue to be productive at, say, age 32. But players like him are the exception rather than the rule. Rarely is it a good idea to lock up defensively challenged sluggers like Alvarez; even more rarely is it a good idea to commit oneself to a big-money deal with a pitcher.
So I don't think the Pirates' willingness to lock up players to "marquee deals" should be that much of an issue, though Finder is clearly right that fans will make it one if the Pirates have any success. The main project should be developing enough players good enough to press the issue. And payroll will need to rise, but not primarily because of marquee contracts. Rather, young stars' salaries will rise as they become eligible for arbitration, and they will need to be complemented with free agents when they're ready to contend. Many fans surely will make "marquee deals" the issue, but reluctance to do those sorts of deals hasn't been the Pirates' problem in the past, and it's unlikely to be their problem in the future.