"Jon and I have talked about how great it is to play here. He knows that," said Dempster, who pitched 16 seasons in the majors. He will be a special assistant to Cubs president Theo Epstein and general manager Jed Hoyer.
"[Lester] has an extremely tough decision ahead but whatever the decision is going to be, hopefully it's here with the Chicago Cubs. He won't be disappointed. The city of Chicago will embrace him. He's the type of person that could pitch here and do well here and do well in this city."
Dempster pitched for the Cubs for nine seasons (2004-12) and is the only player in team history to have more than 50 wins and 50 saves with the club.
"I'm super excited. This is a great opportunity for me," he said. "The best years of my career were here. When I think about playing baseball, I'm a Chicago Cub at heart."
Now he's hoping to persuade Lester to come aboard. Dempster touted Lester's leadership in addition to his ability.
"A guy like Jon Lester is going to prepare just as hard when times are going tough," Dempster said. "That's when you find out a guy's true colors. He's that kind of guy. It's [leadership] a very valuable tool. It's just as valuable as the performance."
The Cubs have actually made an offer higher than the $130 million to $140 million that has been reported, according to a source familiar with the situation.
Lester is expected to command more than $150 million on the market, and if a team completely blows past that number, the Cubs probably would bow out, just as they did when the bidding for catcher Russell Martin shot up.
"Free agency is important, and you have to be aggressive to get something done in this current landscape," Epstein said Friday. "A lot of teams have money. There's more demand than supply for elite players.
"You also have to maintain some sense of discipline and limits and long-terms perspective. If you go into free agency thinking you're one player away and you need any one player at all costs, you're probably going to end up getting burned."
The two-time All-Star finishes his playing career with a 132-133 record, 87 saves and a 4.35 ERA in 579 appearances. He also played for the Marlins, Reds, Rangers and Red Sox during his career.
"Hopefully I can provide a little bit of insight once in a while," Dempster said of his new position. "I'll do whatever Jed and Theo need me to do."
Dempster also will continue as a commentator on MLB Network.
Dempster Retires, Will Work In Cubs' Front Office
Jesse Rogers discusses the career of pitcher Ryan Dempster, who announced his retirement as a player and his intent to work in the Cubs' front office.