Ryan Dempster appears to be recruiting free agent Jon Lester to Chicago

Former Chicago Cubs pitcher and recently hired front-office assistant Ryan Dempster appears to be working on recruiting free agent Jon Lester according to ESPN Chicago’s Jesse Rogers.

Dempster, 37, retired as a member of the organization earlier today and accepted a position beside Cubs’ president Theo Epstein. It’s no secret that Chicago is willing to spend a truck load of money for top-notch pitching, and Lester is at the top of their wish list.

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The two won a World Series together as members of the Boston Red Sox just last year. Dempster told reporters that he mentioned to Lester how great it was to play in Chicago – a place where he was loved by everyone.

There are multiple teams in the hunt for Lester’s services this off-season but a decision regarding where he will land won’t be made anytime soon according to a couple of sources across the league.

“He knows that. He 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.” Dempster via ESPN Chicago.

Theo Epstein’s assistant went on to tell reporters that the city of Chicago will embrace him and that he’s (Lester) is the type of person that could not only pitch here, but do well with the organization and the city.

You would have to think that the price tag for Lester’s new deal could be $150 million or a little bit beyond that figure considering the offer that was submitted by this organization.

It was reported a week ago that the Cubs extended a “significant offer” to Lester and his camp that was somewhere around $135 million or more.

Although the contract does sound like a mouth-watering deal, the Boston Red Sox could find a way to one-up the hopeful North Siders after finding a way to land both Hanley Ramirez and Pablo Sandoval within days from each other.

Not to mention the Los Angeles Dodgers looking to add another pitcher to their rotation to compliment back-to-back NL Cy Young winner Clayton Kershaw.

Even if the Cubs missed out on Lester, don’t be surprised if another piece of the Tampa Bay Rays’ past catches wind of what’s going on in Chicago.

James Shields went toe-to-toe with Lester in that extra innings AL Wild Card game in Kansas City on September 30 and rejected a qualifying offer from the club.

Shields spent some time with both Joe Maddon and Dave Martinez in Tampa Bay before finding himself with the Royals from 2013-2014.