Lester talked specifically about the impact of being traded after he signed with the Cubs. It didn't enrage him, but it opened his eyes to the fact that he could play for another team/city and it wouldn't be the end of the world. Up until then he assumed he'd be staying a Red Sox, because that's what he wanted and was willing to be flexible about it. Then he was traded, and once that mental threshold was crossed, he was open to the idea of exploring the free agent process to its fullest.
A lot of truth in what you say. It's like being dumped by a girlfriend who demands you stay in her life, and you're down and out about it, and then you end up meeting someone else.
The timeline
10/13 = Red Sox win World Series. JL is the best Sox pitcher in the mix.
3/14 - :JL declares his love for Boston and the Red Sox and states he'd like to negotiate a future long-term contract. Red Sox counter by making an offer he can't accept.
4/14 - as the regular season beings, JL states that he will put the negotiations off until season's end. Avoid the distraction.
7/14 - comes the All Star break. Widely reported = Red Sox are desperate to have him sign a contract. Widely known = Red Sox are having a season in which they will end up in the cellar, and the only proven pitching performer is .. JL.
Widely reported = JL says "no means no. Let's talk in November."
mid 7/14 - JL pitches his last victory for the Sox a 6-0 gem against the Royals at Fenway. Later in the week he has a 2-0 lead to be blown by the pen, vs. the Rays, a no-decision for JL. His last Red Sox appearance.
late 7/14 - Sox 13 games out, having lost 9 out of 11, down from 7.5 down at his last win. and on their way from a first-to-worst classic season, trade JL to Oakland for their best player (Cespedes), a move that Sox fans understand, Athletics fans are riled over it. Classic scene has JL and wife Farrah leaving Fenway in their SUV, John Henry wishing him luck and expressing wishes that he'll be back next year.
10/14 - JL loses WC game in KC. Oakland is out. After the WS, JL is a free agent.
11/14 - Discussions ensue with several teams, including the Red Sox. Comparable offers, allowing for tax differences, are made by the Giants, Cubs, and Red Sox. Others make offers, but the Lester camp concentrates on these three.
12/6/14 - John Henry is reported, by multiple sources, to travel to Lester's Georgia home for a 1-on-1 session to try to convince him to stay. Offer now is supposedly six years, and in line with what other teams are proposing. Lester had his Newton home on the market, but even if it sold, he now has the money for an upgrade. The ESPN story reports =
"After meeting with the Red Sox last week, Lester's agent, Seth Levinson, noted the "great respect" the team accorded Lester, who has repeatedly said he is not necessarily signing for top dollar but looking for the place he finds most comfortable."
This gives the Sox, and their fans, some hope that the hatchet from bad negotiations in March are buried. It could also lead to something more ominous.
12/15/14 - Lester signs with the Cubs, opting to rejoin Theo Epstein and Jed Hoyer, favorite catcher David Ross goes with him.
12/16/14 - Christmas at Fenway is a completely depressing event. Instead of greeting fans inside the Royal Rooters club, team officials opt to conduct their interviews outside, out of view and avoiding those who chose to attend.
October 2015 - Cubs finish 90-72, 3rd, winning record. Win wild-card, NLDS, but lose in four straight in the NLCS to the Mets. In the meantime, the Sox finish 78-84, in the cellar again, and replace GM Ben Cherington in August.
October 2016 - Cubs win World Series. Red Sox finish 1st in the AL East and take an immediate dixie , 3-0, to the Indians.
Note the most significant report above =
"looking for the place he feels most comfortable."