The Cubs believed in Lester enough to give him the richest contract in team history. Lester bought into what the Cubs’ front office was selling: the chance to break a 106-year championship drought.
“As soon as we left the meeting [with the Cubs], we had a good feeling about what they were bringing to the future of this organization,” Lester said at a Monday news conference. “The belief they have here made us believe they aren’t going to be in last place for very much longer.
“I don’t like to lose. You can call it arrogant or cocky or whatever you want. I like to win. That’s what I’m here to do.”
If nothing else, you come away with the impression that Lester is a serious man and that he wasn’t just signing on with the Cubs because of the $155 million they’re paying him. The money certainly doesn’t hurt, but the commitment might have sealed the deal.
“Theo [Epstein] and Jed [Hoyer] were relentless, detail-oriented and sincere,” said Lester’s agent, Seth Levinson. “They demonstrated their vision of success in a manner that gave Jon great comfort. In the end, Jon placed great faith in his relationship with them and was confident in the plan.”
It was a perfect storm for the Cubs. Consider all the following that played a part in their favor:
Lester was given a lowball offer by the Boston Red Sox last spring, which enabled him to eventually become a free agent. He says he holds no grudges, but it set the stage for his entry into the market.“When you sit down at the beginning of the season, you think, can we get an extension done with this team? And if we don’t, what are some teams you would be interested in going to?” Lester explained. “The Cubs were on that list.”
Lester was traded for the first time in his career last season, as the Red Sox moved him to the Oakland Athletics in July. He admitted it might sound silly, but leaving your comfort zone isn’t easy for a baseball player. When it happened once, it led to happening again. This more than anything might have paved the way for the Cubs.“When I got to Oakland it was good,” Lester said. “It helped prepare me for this situation. That broke that barrier of, ‘I wonder if I can play for another team?’”
The Athletics never had any intention of re-signing him.
Being traded to the Athletics brought him together with former Cubs Jeff Samardzija and Jason Hammel. They and former teammate Ryan Dempster had a big impact on Lester.“[Dempster] had nothing but great things to say,” Lester stated. “Obviously, I wouldn’t be here today if those guys didn’t speak highly of Chicago.”
“As far as winning, are these guys close? That was my question to Jeff. Are they there?”
Again, it went back to a belief and a trust in Epstein. He had built a winner in Boston, and Lester thinks he can do it again in Chicago.
“I believe in the plan they have in place right now for the future of the Cubs,” Lester said. “Leaving a place where you’ve already won is difficult, but I also relish in the chance of winning a world series for a franchise that never has [in a long time] adds a little extra for me.”
Epstein said the feeling was mutual.
“It was about belief,” he said. “We knew early on if we signed Jon Lester, it would be about belief. He would believe in us, believe in our future and believe in winning a World Series -- [it] would be a unique opportunity.”
What about Cubs ownership? Tom Ricketts had to sign off on the $155 million deal with a no-trade clause. It took one meeting with the pitcher to convince him.
“I had dinner with Jon and got 100 percent comfortable with the person,” Ricketts said. “I don’t have any real concerns. Jon has earned the right to have that kind of contract.”
Once both sides believed in each other, it came down to the contract. Epstein says the Cubs made an offer hoping a deal could be struck with the “turkey in the oven” around Thanksgiving. They adjusted it leading into the winter meetings and fine-tuned it once in San Diego. Then the waiting began. The decision came late on Dec. 9.
“We made it hours before it was announced,” Lester said.
Ricketts said the deal went into the wee hours.
“It was really late at night,” he said. “It wasn’t 100 percent until 2 a.m. It was good. I don’t think there was anyone out there we would have made this commitment to.”
Epstein was confident and was even ready for a hunting trip with Lester, if it was needed.
“I was prepared to,” he joked. “I was ready to soak myself in deer urine, if necessary.”
At the end of the day, all parties got what they wanted. The Cubs got their ace. Lester got security and a promise from his new team that they were playing to win. And Ricketts might even have shed the “cheap” label he’s worn since buying the Cubs.
“Maybe that’s nice,” he said with a smile. “I don’t have to read it.”
For Lester, there were two parts to the whole process. Meeting with teams was the fun part; making a decision was much tougher.
“It felt like the right fit for us at the right time,” he said. “I’m going to put my head down and go to work and do everything I can to succeed.”