I don't think all 3 signings in 2008 were bad. Sure AJ was overpaid and a bust but CC and Tex's weren't bad. CC's numbers during the 2009 playoffs (when he had been HORRIBLE his previous 3 times pitching in October) were:

5 games, 36.1 innings, 28 hits, 8 ER, 4 HR, 9 BB, 32 SO, 3-1 with a 1.98 ERA.

During his time in New York, he's been a work horse. Pitching at least 200 innings in all 5 seasons with the Yankees with an ERA as high as 3.38 prior to the 2013 season. Now sure, this season he took a step back but let's not hit the panic button just yet. And they had to add that opt-out clause as a way to entice him to come to New York. I remember when he hit the free agent market, everyone was predicting him to go to a California team since that's his home state. The Yankees had to throw that clause and money at him to get him to come to New York and in my opinion, it's worked out.

As for Teixeira, I don't consider him brittle. Here are the number of games he's played during each of his 5 seasons with the Yankees: 2009 (156), 2010 (158), 2011 (156), 2012 (123), 2013 (15). So again, take away 2013 and he's averaging 148 games his previous 4 years. And, what a lot of people seem to undervalue or forget about is his defense. Not only is he a switch hitter who usually puts up 30 HR and 100 RBIs but he's won 3 Gold Gloves as the Yankees first baseman.

I agree, the smart move for the Yankees would be to sign future talents to short term contracts that pay a lot (like Josh Hamilton's 5 year, $125 million contract with the Angels). The only problem is, they're competing against other owners who'll give them those extra years and if they want that talent bad enough, they've got to meet or exceed that contract. Otherwise, they won't get them. But the 10-year deals are dumb for ANY team to hand out. The Yankees did it with A-Rod, the Angels did it with Pujols, the Dodgers are thinking of doing it with Kershaw. Heck, I'd still say it'd be a somewhat stupid move if the Angels did it with Trout because that's so many guaranteed years and who's to say what will happen 4 or 5 years down the road?