Cubs expected to heavily pursue Jon Lester this offseason

With a treasure trove of talented position players and very little guaranteed salary on the books, the Chicago Cubs are expected to be major players in the free agent market over the next few offseasons, as the club looks to supplement a core of very talented young players in order to finally return to the postseason. According to Patrick Mooney of CSNChicago.com (writing for NBC's Hardball Talk), current Oakland Athletics' left-hander Jon Lester is expected to be among the players pursued this offseason, as sources tell Mooney that the club is currently "targeting" Lester and intends to "make a run at him this winter." Indeed, the Cubs had pro scouting director Joe Bohringer watching Lester during Tuesday's start against the White Sox, just across town from Wrigley.

While Lester has been continuously linked as a possible candidate to return to the Boston Red Sox this winter, it's not surprising that Chicago would have such an interest in adding the three-time All-Star, as he so clearly fits a need and already has an established relationship with Chicago's front office.

Cubs have Pro scouting director watching Jon Lester pitch . Not that the front office needs too know much about the pitcher .

— Bruce Levine (@MLBBruceLevine) September 10, 2014

Originally drafted by Boston in 2002, Lester's tenure with the Red Sox organization overlapped for nine years with that of former GM Theo Epstein, who left the Red Sox following the 2011 season to take the reins in Chicago. The familiarity between Epstein (along with GM Jed Hoyer and vice president of player development and amateur scouting Jason McLeod) and Lester is clearly evident. They won a World Series together in 2007, and Epstein signed Lester to a $44 million extension in 2009. In 2006, Lester successfully battled non-Hodgkin Lymphoma, and returned just a year later, starting game four of the World Series.

Even with a plethora of highly regarded young hitters that includes names such as Anthony Rizzo, Javier Baez, Addison Russell, Kris Bryant, Starlin Castro, and more, the Cubs are still lacking in high-quality pitchers, especially after dealing away both Jeff Samardzija and Jason Hammel this summer. While Lester is not young (he's 30), he's been about as reliable as they come over the past seven years, logging at least 190 innings every year since 2008, and posting an ERA+ of at least 110 all but once during that time. Adding Lester would give the Cubs' some certainty atop their rotation, while also providing them with the ace that they so clearly lacks.

For a rebuilding club, Lester's freedom from draft pick compensation (due to July's trade to the Oakland Athletics) is another huge plus, and although that may lead to an increase in his total payday, there is little doubt that the Cubs can afford to pay him. As it currently stands, the Cubs have less than $30 million in guaranteed salary committed for 2015, so pricetag shouldn't be a problem.

Some may also question the timing of a Lester signing, as the Cubs are probably not going to be contending next season. However, with a number of top prospects debuting this year and next, it shouldn't be long before Chicago is a winning ballclub again, and if the Cubs view Lester as the GUY, then this is their chance to go and get him.

Of course, it's easy to see Lester landing in Chicago on paper. Realistically, the Cubs will be just one of many teams vying for a pitcher who is currently fourth in the majors with a 5.6 fWAR, and that will certainly be a major obstacle. Among the clubs that are likely to pursue Lester are the Yankees and Red Sox, both financial powerhouses who could engage in a bidding war that makes Lester no longer worth signing for the Cubs. There is also the oft-rumored possibility of Lester returning to Boston, a city which he has called home for the last nine years prior to this July.

If the Cubs are unable to land Lester, they could turn their attention to Tigers' right-hander Max Scherzer, though he will certainly cost more than Lester (having already rejected a six-year, $144 million offer from Detroit) and force the Cubs to surrender a draft pick (though only a second rounder since they will likely finish with one of the ten worst records in the league).

The Cubs aren't out of the woods just yet, as there is plenty of development still to come on the position player side of things, and Theo and co. still have to accumulate the necessary pitching to contend. Jon Lester could be the solution.