Jon Lester announced his retirement Wednesday after 16 seasons in Major League Baseball worthy of Cooperstown consideration.
Since then, he’s been reminiscing on those years, most of which he spent between the Boston Red Sox (2006-2014) and Chicago Cubs (2015-2020). Oddly enough, his winning percentages and ERA were identical with both teams, showing how dominant and reliable he was throughout his tenure.
Boston came close to benefitting from a lot more of what the five-time All-Star had to offer. Lester was a free agent at the end of 2014 for the first time in his career, and told the Barstool Sports “Section 10” podcast he potentially wanted to go back to the team that drafted him.
“I would say a high percentage,” Lester told host Jared Carrabis. “I mean it was up there and you know, we wanted them to be the first to come in. So they came in the whole crew came in and sat in my living room and we talked and and I thought after that meeting and after seeing the offer and them leaving, feeling really good about it.”
Lester continued on, explaining that when the Cubs came into the picture, everything changed.
“We all want to feel wanted, right? Like you always want to feel like they’re not just signing me because the fans want me back. Like they actually want me to be a part of this rotation — and not to say that they didn’t. But I feel like the Cubs really made me feel wanted.”
Things turned out well for Lester, of course, who helped bring another historic club to dominance for the first time in 108 years and etched another part of his legacy.
But for Boston fans, there will always be that, ‘oh what could have been.”