With the front office placing pitching at the top of the off-season wish list, the Cubs will be connected to just about every free agent starter on the market. The Cubs are believed to be looking to add a top of the rotation-type starter, or two, over the next two off-seasons.

The industry buzz, as Ken Rosenthal put it, is that Jon Lester will sign with the Cubs in the off-season. Lester makes sense for the Cubs for more than one reason. Not only is there a connection to the front office from their days together in Boston, but Lester would provide a veteran presence at the top of the rotation that could pitch the first game of a playoff series. Plus, signing Lester would not cost the Cubs a pick in the draft or the allotted slot money. Under the Collective Bargaining Agreement, Oakland cannot make Lester a qualifying offer.

Beyond the big name free-agent starters, Jon Lester, James Shields and Max Scherzer, there are the likes of Justin Masterson and Jason Hammel that could be of interest to the Cubs this winter. The two right-handers have already been connected to the Cubs by the mainstream media and both Masterson and Hammel have a history with the Cubs’ front office.

The Sun-Times reported in late-July the Cubs were having internal discussion about Justin Masterson. And a report from Comcast SportsNet less than two weeks ago indicated Jason Hammel could fit in to the Cubs plan and he would be interested in re-signing with the Cubs.

Justin Masterson was at Wrigley Field this week and Patrick Mooney spoke with him about what he thought about signing with the Cubs. Mooney reported that Masterson sounded “interested in the idea of coming to Chicago.”

Masterson explained to Mooney that he “lives in Indiana, grew up in Ohio, went to school in South Bend, so all of those people love the Cubs. When I came to St. Louis, they were all like: ‘Ugh, this is really hard to deal with.” Masterson said he would sit down with his wife and agent after the season ends to the options. Masterson admitted he likes the Midwest and it would “be nice to be somewhere close to home.”

Justin Masterson has really struggled this season, with both the Indians and the Cardinals. Patrick Mooney reported the oblique injury he dealt with last year might have contributed to the knee and mechanic issues he’s had this season.

After posting a 14-10 record in 32 games, 29 starts, with a 3.45 ERA and a 1.20 WHIP last year for the Indians, Masterson is a combined 6-9 this season in 27 games, 25 starts, for Cleveland and St. Louis with a 5.97 ERA and a 1.65 WHIP. Masterson has really struggled since the trade and pitched his way out of the Cardinals’ rotation (2-3 in eight games, six starts, with a 7.53 ERA and a 1.64 WHIP).

Patrick Mooney posted the disclaimer in his report that “the Cubs are going to kick the tires on just about everyone this winter.”

Masterson has not spent a lot of time thinking about his future. He told Mooney he enjoys the National League and he’s noticed the success other pitchers have had with Chris Bosio. Masterson admitted he is hoping there will be a lot of options for him this winter.

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