In the long run we're all dead. So what?
Cliff Lee signed a 5 year contract worth $120 million after 2010. In the three years following that contract, he put up 17.3 WAR. In the last 2 years of the contract he put up 1.9 WAR, including a big fat zero last year. Add it up and it's 19.2 WAR for $120 million, or about $6.2m/WAR. In other words, a pretty good contract.
Roy Halladay signed a 3 year extension (basically a 4 year deal) for $75m when he got traded to the Phillies after the 2009 season. He sucked in 2013. So what? In 2011 alone he was worth
$63 million. At $7m per win, Halladay was worth $114 million over the life of his contract.
Adam Wainwright signed a 5 year extension worth $97m at the beginning of the 2013 season. Since that time he's put up 12.3 WAR at $60m, for a terrific rate of 4.8 $/WAR. I don't see the Cardinals shopping him to get out of the final 3 years of his contract, and I doubt they consider him an albatross, but he only needs 2 more WAR for the remainder of his contract to have proven average value over the lifetime of the deal.
How about Sabathia? His contract was originally $180m over 8 years, which was reportedly $60m more than anyone else was willing to pay. Since signing that deal, he put up 26 WAR. At $7m per win that's $182 in value, for which he was paid ~$150m. So he has already earned his original contract. He'll have trouble living up to the extension the Yankees gave him in 2011, and the Sabathia opt-out extension is the first contract signing that I have down as a probable mistake.
Verlander will be an interesting case, but even here he has been basically even to the Tigers relative to the $7m/WAR baseline: 10.6 WAR is $74.2 in value against a little over $25m AAV over the past 3 years. Obviously, that's not great for the Tigers because the whole point of these contracts is to accumulate excess value in the early years of the contract which makes up for the albatross at the end. On the other hand,
Verlander was pretty fucking good last year so the story is far from over on him
But he's the only one - the rest of those guys all look like solid value to me. Fangraphs has King Felix at $260m in value since 2009 and $110m in value since his signed his 7 year, $175m deal before 2013. So he only needs another 6 or 7 WAR over the next 4 years to provide average value for Seattle.
Fangraphs has David Price worth over $90m over the past 2 years. 90! I don't know what the $/WAR is going to look like over the next few years, but with the money flooding in to this sport it sure isn't going down. At $8m/WAR he needs to reach 26 WAR to be worth that contract. I'd say $9m/WAR is more realistic, which puts him at 23.3 WAR. That's about equal to his performance over the past 4 seasons.
So we're basically betting on Price accumulating the same degree of value over the next 7 years that he already accumulated over the previous four. He can do that by having four great years and then falling off a cliff, or a couple of great years followed by a more gradual decline, or by being decent throughout, or whatever. The chances of him being worth his average salary by year 7 are low, but then the chances of him being worth more than his average salary in year 1 of the deal are very high.
I'd say the big picture thought I have about this whole exercise after having done it all is that it's much more important to avoid a complete collapse like Lincecum than getting too concerned about the total dollar figure for a Price or a Greinke. Obviously Lincecum had major red flags right from the beginning, as does, say, Cueto.