In response to ma6dragon9's comment:
In response to Flapjack07's comment:
The problem with the "pink hat" epithet is that it just ends up getting used to denounce whatever position someone disagrees with, whether it makes sense in that context or not.
You can argue whether we should or should not extend Jon Lester, or whether it would be worth it at this price but not at that price, but I hardly see how having a certain opinion on that subject makes a person a "pink hat."
I think Lester SHOULD get extended. Just not at 20per.
To me, people convincing themselves that 20per is any kind of hometown discount is laughable. If they had given him 20 per, when he was 27, for 6 years...you could justify that. And, well...let me backtrack...I actually WOULD give Lester 20per year...for 2 years. But annual amount AND length? No. That's not what you do when you sign a guy early unless you're a team like TB or MIL who is legitimately small market and HAS to extend early like that. And then, those teams NEVER do it with a 30 year old because the risk is simply too high, and they rarely, if ever, pay off.
Due to the fact that very few top of the rotation starters ever reach free agency anymore, and more teams have money to spend than ever before, pitchers of Lester's caliber are going to get paid big dollars if they do test the market. It would be wise to lock up Lester now, which seems to be the plan. The only way he gets less than 20 million per is if they sign him long term (6 years or more). If they go 4 years or less, the average annual value will likely be around 23-25 per. I'd be willing to bet on it.