Cubs Expected to Be Aggressive as Main Focus Shifts to Pitching

The front office has already started planning out the off-season and what lies ahead for the team in what should be an important winter for the Chicago Cubs. Theo Epstein and Jed Hoyer have talked about the team being ‘aggressive’ with adding pitching and it will be the front office’s main focus this off-season and for the next 12-24 months.

Many are expecting the Cubs to target Jon Lester as soon as he hits free agency. Lester will have a hefty price tag, think in the six-year and $140 million range, but signing him would not cost the Cubs a second round selection in next year’s draft or the assigned pick value.

Lester is familiar with the Cubs’ front office, obviously from their days together in Boston, but despite Ken Rosenthal’s report that Lester’s former teammates think he will end up with the Cubs, there will be a lot of competition to sign Lester.

The Cubs have been linked to other free agent starters by the mainstream media, such as Max Scherzer, Justin Masterson and Jason Hammel. And while James Shields will also be high on the free agent starting pitcher list throughout baseball, Shields turns 33 in December and would seemingly not fit the Cubs plan based on both his age and workload. Lester will pitch next season as a 31-year old and two years with an additional 300-plus innings in the regular season is a lot when a team is looking at the type of long-term contract both pitchers will demand, and receive.

PrintThe Sun-Times reported that the comments Jon Lester made to the Boston Herald about his comfort level being more important than signing the biggest contract this winter “seems to put the Cubs and Red Sox in the front-runner positions” for Lester.

According to a report from Bruce Levine, Darnell McDonald, Lester’s former teammate in Boston “will be used in the recruitment process.” McDonald was added to the Cubs front office as a Baseball Operations Assistant in April.

Travis Wood

The Cubs reportedly approached Travis Wood last off-season about signing a long-term extension with the Cubs before his first year of arbitration eligibility. But as quickly as those reports surfaced, they went away with reports prior to Spring Training suggesting that Wood decided it was best for him to go year to year. Wood was coming his best season in the majors and according to a report earlier this week from the Sun-Times, Wood decided to wait on signing an extension.

According to Bruce Levine, Wood’s agents “may rekindle talks with the Cubs this off-season” after tabling those discussions in the spring.

Travis Wood, like Jake Arrieta, sees what the Cubs are building and understands baseball is a business. Wood acknowledged he’s “not had the best season” and wants to “finish strong.”

Rumors and Notes

The Sun-Times reported the Cubs might not be done making trades this season. According to the report, Jed Hoyer said there could be “some action at the end of the month” as teams put players on waivers that they did not try to send through in early August.

Jed Hoyer told David Kaplan and David Haugh Friday during his weekly segment on the Kap & Haugh Show that the team is working on its plans for the final six weeks of the season and the Cubs will do different things with the rotation in September. Hoyer did not expand on what those “different things” may be.

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  • Jeff Wilson

    “and the Cubs will do different things with the rotation in September. ”
    With the upcoming tight schedule, I imagine this means going to a 6 man rotation maybe?

    • Jeffrey Rogers

      Yes…. and / or skipping some of Edwin Jacksons starts and possibly taking Wood or Arrieta out of games early.

      Not sure how many inning Hendrix has pitched this year but I would guess they would not want to push him much past his personal high.

  • redlarczykg

    The Cubs could do “different things” with their rotation if Edwin Jackson suddenly pulled a hammy getting out of bed or slipped in the shower.

    • Jeff Wilson

      “had an accident, so to speak”!
      If you took out every start that Jackson made this year, not counting the wins, not counting the losses, I wonder what our W-L record would be.
      Might be something that I do tomorrow when I’m off work…

      • Sahm

        War would tell that right

  • Jim Canavan

    Theo has been hit or miss on pitching. At the major league level, He has missed on Ejax and Veres Big Time. He has hit on Feldman, Hamel, Wright and done a decent job on acquiring minor league talent.

    • Jeffrey Rogers


      If they are as successful at overhauling the pitching rotation as they have been at acquiring minor league talent it will be a very exciting brand of baseball at Wrigley in the near future.

    • Tony_H

      I would love to see what the farm system would look like today if you were to think it was just a good job. #1 system already.

  • Roe Skidmore

    Move Jackson to the bullpen, he doesn’t deserve any more starts. Maybe he can pitch an inning or two and thrive, like Dennis Eckersly? Who knows?

    • J Daniel


  • baseba11fann

    “but signing him would not cost the Cubs a second round selection in next year’s draft or the assigned pick value.” In the current CBA any player traded at mid-season the team that traded for him gets no compensation so it would only cost money

    • Neil

      Thank you for reiterating the point about not costing the Cubs a pick in the draft.

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