Boston really did a great job in recognizing a lost season and doing what it can to make sure 2015 can bring a contender. Lester is great, but he will be entering his Age 31 season. Historically speaking, 6-8 year deals for pitchers don't turn out well, especially after 30.
Pitchers generally don't come into their own until around the age of 30. I can name off hundreds, literally, who have pitched well (and improved) into the mid to late 30's.
Lester has been amazingly inconsistent his entire career, only lately coming of age. Every season, prior to this one, Lester started the season in awful fashion. AWFUL. To the tune of 0-3, 0-4, ERA over 6.00 or even 7.00. He would get things straight and then after mid season he would have a stretch where he would bottom out again before getting "right" again. For the longest time he was also a nibbler. Lester could not make it out of the 6th inning to save his life.
Lester threw harder a couple years ago, he has lost a couple MPH on his FB and cutter. He touched 100 a couple times here in Portland, back "in the day." He used to live in the 97-98mph range. He's gone from a thrower to a pitcher. He's only going to get better. Barring injury, Jon Lester is going to be a legit 1 or 2 for the next six to seven years. As he loses a little velocity he keeps finding ways to get people out. His control has become sick.
I didn't really weight in on my opinion on this trade. I'm going to say this, right now:
It sucks. Hard. Here is why.
Each organization should have a philosophy, a "mission statement" as it were. Theo came in and the Red Sox decided their philosophy was a build from within and supplement with occasional free agent signings. Keeping in mind I actually worked in the scouting department in the low A level, here are the key developmental areas the Sox stated were priorities for their "philosophy:"
1: Pitching
2: Pitching
3: Pitching
4: Pitching
5: Pitching
6: Infield
7: Pitching
Now, this was under Theo's watch. He wanted to groom pitching, pitching, and more pitching. He wanted to do it for the following reasons:
1: Organizational growth. When you develop your own front line starters (and bullpen) you become less reliant on the "outside world" on the hardest to find commodity each year. Theo's "grand vision" was to have at least 65-70% of the starting rotation be "home grown" and 40-50% of the bullpen.
2: Export chips. When you place an inordinate amount of resources in one position, other positions are going to suffer. It doesn't take a rocket scientist to understand the Sox inability to draft skillfully at specific positions during a certain period of time. While they hit on some players (Moss, Reddick, Hanley) most were abject failures. Boston could not draft a power bat, or a catcher, to save their lives. The reason why is they didn't have the talent in the field to spot the talent to do so. My assumption is they had a bunch of guys like me out there. I know pitching. I couldn't properly evaluate a major league power hitting first basemen with a gun to my head (Lars Anderson, anyone).
If you have a stable of power arms, however, you can trade some away. Those trades can net you the likes of Victor Martinez, or Mike Lowell. While Justin Masterson is a fine pitcher, he didn't fit into Boston's plans. He would have sat in long relief, same with Sanchez. They turned both "chips" into valuable pieces.
But there are some "chips" you keep. At all costs. I'll discuss two.
Jacoby Ellsbury, one.
There is a massive reason Boston's offense is struggling, and Ellsbury is a really big reason why. This was one rare "hit" for Boston's scouts in the Theo days, and a massive one. Gold Glove caliber defense, impeccable work ethic, doesn't cause any drama in the club house, always hits over .300, and a spark plug on top of your order. When Ellsbury starts to lose his speed he will still be faster than 95% of the league. Unless you've been on the field and watched him sprint (I have) you can't comprehend how fast he is. Potential for 10-15 home runs per year. He has three amazing tools and 2 additional really good ones.
You keep this guy, and you build your defense around him.
Jon Lester, two.
After years of inconsistency (regular season), Lester owns the best ERA in the history of the game in the World Series. He is a beast in the AL East. He is durable. He is money in the post season. He is a club house leader. He is a stable in your community. You've literally scouted the kid since high school. And now, because he is over 30, you've decided to let him walk? This is when you push your chips in. This would have never happened under Theo, and I agree.
Pitching and strength up the middle, with some pop at the plate.
I like Jackie Bradley Junior in center field. On defense he may be the best I've seen since Fred Lynn. He's that good. But he's overmatched at the plate, and he's not ready. He may never be. Owens (currently at AAA) is a beast. Lester came up at 21. Owens is 22. Maybe he will be the guy who will buck the trend and be okay at 22 in the bigs. Or maybe, like all young pitchers, the "old salty vets" will figure him out quickly...just like they do to all the "next big thing."
Why? Because pitchers get better with age.
I don't want a thunder bat in the outfield. I want the players we scouted and spent years grooming and investing in. I want Ellsbury and Lester. It's flat out stupid, and wrong, the Red Sox ownership are trying to play the "small market" game now.