(670 The Score) As Cubs left-hander Jon Lester worked in Chicago's eventual 3-2 win against Cleveland on Wednesday evening, it didn't dawn on general manager Jed Hoyer that it could be Lester's final start at Wrigley Field.
It wasn't until Hoyer stopped by manager David Ross' office after the game and heard a few individuals discussing it that it hit him. With the Cubs on the road for Lester's next turn in the rotation and then the final three rounds of the playoffs being held at neutral sites, Lester might not pitch again at Wrigley Field. Lester is in the final season of his contract.
"Who knows what future holds," Hoyer said on the Danny Parkins Show on 670 The Score on Thursday afternoon. "There's no way to be able to forecast it in this year of having things be so difficult to forecast. If it actually was (his last start at Wrigley), he's the biggest and best and most impactful free-agent signing in club history. His influence and his impact on this organization is sort of beyond reproach. It's very rare that you set a plan and it works out almost exactly as you want. But in the case of Jon, what we signed him to do both in the clubhouse and on the mound, I mean you can't deliver more than he did. We wanted a guy who could come in here and change the mentality of the organization. We wanted a guy who could pitch in huge games for us and have that experience and a guy that's sort of the ultimate competitor that we knew would bring that fire and change the way the clubhouse acted every fifth day. And he did that and then some.
"If it was, certainly he goes down in Chicago history for all of the best reasons."
With Lester on his mind, Hoyer reflected back to when the Cubs pursued and eventually signed Lester to a six-year, $155-million deal back in December 2014. Did the Cubs feel they had a "real shot" at signing Lester as they walked into that pivotal meeting coming off a 73-win season in 2014?
"We felt like we had a great pitch and we felt like the relationships in the room were strong, both with his agency and also with Jon," Hoyer said. "We'd known Jon since we drafted him in 2002 (in Boston). And so that familiarity certainly helped. And I don't think there's any way he signs here without that. Because he had to put a lot of trust in Theo (Epstein) and being able to execute the plan that he laid out. I don't know that he would've put that kind of trust in just anyone, but he did. I remember it vividly. I remember how much was prepared for that pitch and exactly where it was and going through it and telling him that we felt like in 2015, we could be starting to be competitive but he probably needed to wait a year until we got really good. And it happened faster than we thought – in large part because of him.
"I feel like in some ways we were – I don't want to say pessimistic – but we did not over-promise as far as the team. We said, 'Hey, I think a year from now you'll be really glad you signed here' when you walk through all of our plans and young talent."
After the Cubs broke through and reached the National League Championship Series, they won the World Series in 2016, when Lester was sensational with a 2.44 ERA for the season while finishing second in the NL Cy Young race. Lester made 31 or 32 starts for the Cubs every season between 2015 and 2019.
Hoyer believes the allure of being a leading figure for the Cubs as they aimed to break their championship curse was attractive to Lester, who understood well the story of the Red Sox breaking their title drought in 2004 – when he was in the organization but not on the big league club. Lester later won championships with the Red Sox in 2007 and 2013.
"We sold him hard on being the guy that could break the curse," Hoyer said. "I think it meant a lot to him because in Boston he wasn't there and wasn't part of 2004. He was part of 2007, he was part of 2013 in Boston, but he sort of heard and came up hearing from all the guys about what it was like in 2004. I think he wanted to be part of his own, and I think that meant a lot to him."
What lies ahead for Lester is uncertain. He called the Cubs organization and Wrigley Field home, but he's set to enter free agency at a time when the pandemic has created upheaval with MLB's financial structure.
"There are many conversations to be had in the future," Hoyer said. "It feels very premature to have those, but I am glad people are talking about him today and what he has meant, because he certainly deserves all that praise."
