Jon Lester

Jon Lester: Trade to A's 'broke that barrier' about leaving Red Sox as free agent

December 15, 2014 - 9:50 am

Jon Lester, at the press conference introducing him with the Cubs upon the completion of his six-year, $155 million deal, said that the Red Sox' decision to trade him to the A's at the July 31 deadline (along with Jonny Gomes in exchange for outfielder Yoenis Cespedes) did impact his view of the free agent process. Lester said that it became easier to imagine changing organizations once he experienced success with a new club. (After going 10-7 with a 2.52 ERA in 21 starts with the Red Sox, Lester went 6-4 with a 2.35 ERA in 11 starts for the A's.) "I think so," Lester told reporters of whether being traded impacted his approach to free agency. "We were traded. That was the unknown of going to a whole different coast, a whole different organization, a whole different philosophy. I think going there prepared us for this time. I think if we finished out the year in Boston and you get down to this decision, I think it would be a lot harder. Not to say it wasn't hard as it was, but that broke that barrier of, 'I wonder if I can play for another team.' I think we answered those questions." Still, Lester acknowledged that he agonized over the decision-making process, particularly the final determination about whether to return to Chicago, return to Boston (which offered a six-year, $135 million deal) or consider the interest of West Coast suitors (most prominently the Giants). He fielded countless calls from teammate Dustin Pedroia (among others) before coming to terms with his decision. "I kind of describe the process in two different forms. I think when you're sitting there meeting with people, we got to come to Chicago, meet with these guys, enjoy dinner. We had some other teams that came into our house, meet with those people. I think that's kind of the fun, exciting time. You get to hear different philosophies. You get to meet different people that you probably won't get to be around. And then you have kind of the second phase where you have to sit down and make a decision. That part, for us, was not fun," Lester said at the press conference. "That was a lot of phone calls, a lot of minutes sitting down and thinking about what we were going to do. But as far as the decision-making, we made it literally hours before it was probably announced. Just sitting down with these guys, sitting down with my wife, trying to iron it out, it came down to that final moment where we just put our fist down, said, 'This is it. This is where we're going to go. This is where we feel the most comfortable.' We're not people that are going to put one foot in the pool. We're going to dive in. That's what we did. "Any time you're at a place for a long time, it's obviously a difficult decision," Lester added. "I just believed, like I said, I believed in the plan these guys have. It felt like the right fit for us at the right time. That took a lot of time for us to get to. A huge process that me and my wife and family went through. ... Any time you change something that drastic, it's going to be difficult. But we fully buy in and we take on the responsibility of trying to bring this city a World Series." Lester didn't feel the need to duck either the pressure of that charge nor the target that comes with his new contract, which represents the second highest AAV ever for a free-agent multi-year contract. "I played in Boston for eight years. I think I'm pretty prepared for a lot of things," Lester grinned. "I mean that for the guys here as kind of a joke. I relished my time in Boston. You just have to accept it. I can't change it now. It's next to my name. It will always be next to my name, whether it's a good start or a bad start. ... I just have to believe that I'm going to be prepared every start." The Cubs trust that Lester will be just that, viewing the 30-year-old left-hander as a top-of-the-rotation linchpin for the team's efforts to end a championship drought that dates to 1908. "This is a very, very significant day for the Cubs for a lot of reasons, a lot of great reasons," said Cubs president of baseball operations Theo Epstein. "Obviously we get better on the field. Jon is the perfect pitcher to lead our rotation for where we want to go. We get better in the clubhouse with Jon's character, with Jon's work ethic and his ability to perform at his best when the games matter the most. That sets a great example for other players. We get better in the community. '€¦ Beyond that, this signing really marks a transition of sorts for the Cubs, the start of a period where we're clearly very serious about winning a World Series and bringing a World Series to the Cubs and the people of Chicago."