(AUDACY) We know the Jon Lester story.
Back in the 2014 spring training, the Red Sox offered Lester a four-year, $70-million deal that was remarkably under market value. With the baseline set so low, the Lester camp didn't counter, knowing that the number would have to come in outrageously high in order to meet in the middle. The fear was that the overly inflated ask would be leaked out, sending negotiations off the rails.
Ultimately, the veteran left-hander Lester and the Red Sox never came close to finding common ground, leading to him being traded to the Oakland Athletic in exchange for outfielder Yoenis Cespedes. (In an appearance on WEEI the next offseason, Lester revealed he would've taken a contract in the vicinity of six years and $120 million if the Red Sox had offered it that spring training.)
The Red Sox looped back in the offseason, making a bid to re-sign Lester, but he was in a far different mindset then than he had been nine months earlier. That led to him signing a $155-million deal with the Cubs.
Why the change in approach? In an interview with Patrick Mooney of the Athletic in which he shared advice he gave to former Cubs teammate Anthony Rizzo, Lester offered insight into how his view changed once the 2014 trade deadline deal. Rizzo was traded to the Yankees on Thursday ahead of the trade deadline. He'll be eligible for free agency this offseason.
“That probably was the best thing that ever happened,” Lester said. “Because if we don’t come to an agreement — and then I go into free agency without knowing if I can play somewhere else — I may have taken the safe bet and stayed there. Like I said, everything happens for a reason. Maybe (Rizzo) sees the grass isn’t greener and he wants to come back. Maybe he sees something else and wants to play the free-agent (game). I’m excited for him. That weight on his shoulders has hopefully been lifted. He can just go play and not worry about anything.”
Lester added, "Sometimes you have to kind of hit reset and start over. It sucks. But with the ebbs and flows of our game, it happens and you just have to roll with it.”
Lester is now with his fifth team, having been traded from the Nationals to the Cardinals at the deadline. He signed with Washington on a one-year deal this past offseason, having also expressed an openness for a reunion with the Red Sox when talking to WEEI.com in May.
“I was very fortunate that I got to be a part of a great organization for a long time,” Lester told Mooney. “And then I got to pick another great organization. I got the best of a lot of worlds. Obviously, Rizz and I talked a lot more recently. But I told Rizz that when I was there with the Cubs, ‘Hey, man, the grass ain’t always greener, but sometimes it is.’ He’ll find that out. Maybe it works out to where he does come back to Chicago and this is a two-month stint (in New York). We don’t know what the future holds.”