CHICAGO -- Ryan Dempster knows how good of a pitcher Jon Lester is, and he has already talked to the free agent about how fun it is to pitch at Wrigley Field for the Cubs. Whether that helps Lester make a decision remains to be seen.
Dempster, who was Lester's teammate in Boston in 2013, made his recruiting pitch to Lester before joining the Cubs' front office as a special assistant to president of baseball operations Theo Epstein and general manager Jed Hoyer, which was announced Friday.
"Jon and I have talked about how great it is to play here," Dempster said at the Cubs' offices near Wrigley Field. "He knows that and he's got an extremely tough decision ahead. But whatever the decision is, hopefully it's here with the Chicago Cubs because he won't be disappointed. I know the city of Chicago would embrace him. He's the type of person who could pitch here and do well here. Hopefully, we're lucky enough to have him here with us."
Lester, 30, is weighing offers from at least four teams -- the Cubs, Red Sox, Giants and Dodgers -- and talks between his agents and those teams were expected to continue into the Winter Meetings.
Epstein would not comment Friday on any specific negotiations, but he did say the Cubs were not delaying any other talks with free agents or teams regarding possible trades while waiting for Lester to make a decision.
"We're working on a lot of fronts," Epstein said. "When there's a potential impact player involved, it does shape a little bit the course of your short-term thinking. If you get a player who makes a significant difference in the standings, you prioritize creating a winning roster immediately around that player.
"If the offseason goes in a slightly different direction, you would continue to build more organically and continue to think a little bit longer term."
Dempster said he was impressed by how prepared Lester is before his starts.
"Here I was, a guy who played 16 years in the league, and I'm supposed to be the veteran leader, and I watched him and felt like I wasn't doing enough," Dempster said of their days together with the Red Sox. "If we could add him here, he'd step in front of everybody, and all the young guys could sit and watch and learn from him. He's just a tremendous pitcher and a tremendous human being and would be a great addition to any team."
And now, Dempster said, Lester is seeing the reward of all that hard work by being offered lengthy contracts that will likely top $130 million.
Epstein noted there is more demand than supply for elite players, and said teams need to maintain "some sense of discipline and limits and long-term perspective."
"If you go into free agency thinking you're one player away and you need one player at all costs, you're probably going to end up getting burned and be an organization that's not as healthy down the line," Epstein said. "That said, there are players who are important and there's a time to be aggressive and a time to know what you want and do everything within reason to get it. You have to balance those interests."
The Cubs were aggressive in their bidding for free agent Russell Martin, who took the Blue Jays' offer. As Epstein has said repeatedly, free agency is not for the faint of heart.
"I think we've done a nice job of building up the organization to a really healthy place where we can be aggressive, and we are being aggressive and we'll continue to be aggressive," Epstein said, "but we're not going to enter into any one negotiation as if it's do or die.
"The Cubs are in a really nice spot compared to where we were a few years ago. I think we'll continue to get healthier and healthier as an organization. If we're successful in one or two of the things we're trying to do this winter, we'll be very competitive very soon ... and there are great times ahead."