As a sports fan for the most part over the last thirty years I have learned to root for the laundry but in some cases there are players I really pull for and like and Jon Lester was/is one of those. As a Red Sox fan I do not blame him for going to Chicago. I blame the Boston ownership.
They had a homegrown player, who not only grew up here in the system but met his wife while rehabbing from cancer down in A ball, they saw him beat cancer, get married, have kids, win championships and evolve into a first a class person. In the spring they decided they were going to be slick when he said he would do/consider a hometown discount in the contract extension talks and low balled him at 4/70. They took a player willing to negotiate and killed it with a stupid first proposal. I believe Jon was hurt. Then they traded him because deep down they understood they may not now be able to do enough to make up for that snafu to Jon and his family. They made their bed.
Lester said he would make his decision based on comfort. I believe for him and Farrah comfort = trust. After the spring training offer, the trade, seeing how Theo and Tito and several of his friends like Jacoby Ellsbury were treated on their way out I believe they could not trust John W Henry, Tom Werner and most of all, Larry Lucchino. I think Theo and Jed played this up and to the hilt, there were probably even a few gorilla suit jokes.
I'm also sure Theo and Jed repeatedly asked him and his reps why he thinks the Red Sox ownership has done a brutal job retaining free agents. since they took over in 2002 the list of guys who were lost to free agency or traded just prior to it are staggering: Ellsbury, Damon, Bay, Beltre, Garciaparra, Mueller, Papelbon, Martinez, Ramirez, Youkilis, Nixon the list probably goes on.
Now he is on that list and gone for good and it's really too bad but that all said as a Jon Lester fan I am happy for him and his family. I hope he finishes his career strong.