You don't want to give 5 year extensions for any 30 year old. However, that is going to the pay-to-play price with Lester, especially with free agency being the way it is (a lot of money chasing very few guys). Lester is a lot better than the best guys in this class for instance. He is what he is - an innings horse whose value is both in bulk as well as effectiveness. Yes, I am among those who cite his performance level more like a good #2 than one of the very very elite. But, the fact of the matter is that quality #2 starters, hell even quality #3 starters, who have no injury history and can crank out 200 IP seasons with such reliability, are VERY VERY rare in 2014 baseball. I think the question with Lester is not the length so much as the backside protection for Boston - will they demand some sort of options on years 5 and 6, and will Lester be comfortable offering them.