This weekend, Chicago Cubs’ Chairman and Owner Tom Ricketts took the bold step of extending the contract of the Cubs’ Director of Player Development, Oneri Fleita, for four years, despite the team’s ongoing General Manager search. The step, of course, was bold because that is a position you would think a GM would expect to fill on his own.

Would Ricketts take an even bolder step and extend the Cubs’ Scouting Director, Tim Wilken, too?

Sources tell Bruce Levine that Ricketts will be meeting with Wilken over the weekend of September 16 to discuss the state of the Cubs’ farm system and Wilken’s current contract, which takes him through 2012. Given what just happened with Fleita, and given Wilken’s standing within baseball (read: other teams would gladly hire him), it’s fair to wonder whether Ricketts will offer Wilken an extension as an enticement to pass up other opportunities.

If Ricketts did so, he would have filled two of the most important positions in the new GM’s regime before the new GM was even hired. It would be even more evidence that the Cubs don’t believe they can actually land an Epstein/Cashman/Friedman type.

But, you know…

A part of me does wonder whether these kind of moves aren’t as bold or suggestive as I think. Consider this: we fully expect the Cubs to dump Alfonso Soriano and Carlos Zambrano this Winter, eating tens of millions of dollars in the process. Would it really be so shocking for Ricketts to be willing to eat these personnel extensions, too, if the new GM wants to bring in his own guys?

I actually think the answer is yes, despite the apparent bent of my rhetorical question. Sure, the financial cost would be relatively low – I have hard time imagining that Fleita and Wilken, combined, make more than $1 million per year. But the personal cost would be quite high. What kind of name do you make for yourself when you sign guys – expressly so they don’t take opportunities with other clubs – and then can them a couple months later, knowing all the while that it was how you expected things to play out?

As cold and calculating as Ricketts might be (and that’s a compliment), I don’t think even he wants to start out in baseball with that reputation – it remains a “people” business.

Then again, Levine notes that Fleita’s deal – and whatever deal Wilken might get – will be structured to include flexibility (including healthy buyouts), should the Cubs want to make a change before Fleita’s four years are up. So maybe Ricketts can have it both ways.

  • Mike Foster

    Cold is one thing, shrewd is another. For a small cost he’s keeping options open. I like shrewd.

  • Jeff

    I think signing Wilken to an extension would send up a completely different message than the Fleita signing did.  Fleita is integral to the Dominican project, he leads one of the biggest international scouting departments in baseball, and has been working with many of these countries to scout and develop players since 95.  It always seemed to me that Wilken was the one working closely with Hendry, while Fleita was off in South America or Korea or somewhere working to sign some more hard to pronounce prospects.  I think the track record and the current projects that the team has so much money and time sunk into involve Fleita too much for them to let him walk.  I think Wilken is the more easily replaced guy, and besides, Brett is right.  If Ricketts signs a new gm and then decides he wants someone other than Fleita running international scouting, it won’t be too hard to let Fleita go, especially if they make that decision right after the season ends and give him plenty of time to revisit Detroit and other places that were showing interest.

  • RoughRiider

    I would think that if Wilkin is under contract for 2012 it’s a non issue. Of the 2 I would prefer that Wilkin is retained. Both Wilkin and Fleita have done a terrific job. If it didn’t work out with the new GM they could be assigned other duties and still be paid. Vice President in charge of (insert title here).

    • Brett

      It’s an issue because other teams will over him more years/more money, and the Cubs would likely grant him permission to talk to other teams, given the turnover.

      • RoughRiider

        It’s said that baseball is a business. If it’s in the best interest of the team, the Cubs should not grant permission for other teams to talk with him. The hiring of a new GM should be relatively quick after the season is over. It won’t hurt Wilkin to wait for a decision especially considering his background. If he is as sought after as much as you and I think, he will be retained and if not the offers will still be there 2 or 3 months or even 13 months down the road.

        • Brett

          Thing is, it IS in the best interest of the Cubs to grant permission for other teams to talk to Wilken. An organization with a new “president” (Ricketts) that develops a reputation for being dicks (deny Wilken the right to look around given the Hendry turnover would be dickish) will not get the best people to sign up down the chain. And every employee matters.

          • RoughRiider

            I disagree. A contract is a legally binding agreement that 2 or more parties receive something in return for that agreement. He’s under contract and has agreed to work for the Cubs for a period of time that includes 2012. He hasn’t been told his services aren’t needed and if he is, he will still be paid for 2012. In spite of the way things have changed in the world a MAN lives up to his word and expecting a person to hold to a pact is not being a “dick”. Calling people names is not in my nature but I would and do consider people who do not live up to an agreement akin to your descriptive term. However, if I were Ricketts and Wilkin came to me and said he wanted to resign in order to pursue other opportunities, and he had not been tampered with, I would not hold him to that contract and would wish him well.
            I don’t expect Wilkin to be going anywhere.

            • Brett

              This isn’t about the contract – or about Wilken not living up to the contract (I’m a former lawyer, I understand the contract angle). Baseball is a “people” business, and is a relatively small community. We’re just going to disagree – given the way things have played out, the right thing to do is to let Wilken explore other options if he wishes to. And if other teams want to talk to him, the Cubs should allow that, too. I’m sure he’d be a real happy employee if the Cubs slammed the door on them, and told Wilken: “sorry, we know you don’t want to be here, and we know you had better opportunities, and we know we changed things up by firing your boss… but do a good job for us this year, k?” He probably would do a fine job. And the Cubs would probably struggle to hire top-level good people for the next 10 years. It’s just not the way you do things. It’s neither nice, nor smart.

              • RoughRiider

                I’ve known for some time you are a lawyer.

                As GM I’m not letting Wilkin leave unless he really want’s to and he comes to me and says he want’s to. To my knowledge he hasn’t done that.

                • Brett

                  That’s not the order of things. Team X comes to you first and says, “hey, as a professional courtesy, can we talk to Tim Wilken about his future and a possible job with us?”

                  What do you say?

  • LouCub

    i find it hard to believe that given the money and green light that Ricketts gave Wilken over the last draft that Wilken is going anywhere and since he’s highly respected, I believe the new GM would be foolish not to keep him, especially with the system on the brink of becoming highly productive.It is a big position but like I said there are at least 25-30 more immediate positions that the GM needs to fill so 1 or 2 hires especially considering who they are won’t be a deal breaker..Do you guys actually think that Brian Cashman has 100% say in who’s in the Yankee hiearchy??? Did Theo Epstein replace every single person in the BoSox front office upon taking over?? Hell Andrew Friedman has been getting babysat by Gerry Hunsicker since day 1…Some of you guys are blowing this out of proportion,,,If Ricketts extends, Bush, Quade, Littlefield, Kravec , Gary Hughes etc that’s one thing..2 top guys who gotr the system going up the charts is a no brainer.

  • MichiganGoat

    I’m in agreement that signing Fleita and Wilkens does not directly mean that Ricketts isn’t considering the premier GM names.  Fleita and Wilkens are highly respected and desired by multiple teams and maybe desired by one of the prospective GMs. Regardless I think this is the right organizational decision and if a new GM wants to bring in other people that move can still be made without catastrophic consequences.

    • hansman1982

      MG, its posters like you that have kept me here – thoughtful, reasoned and not immediately Bashing every move that Ricketts makes.

      I agree with you that this means very little in terms of who Ricketts will hire/will be able to hire…

      This may have been more of a message sent to the prospects (that after Hendry was fired were upset that he was let go after negotiating with them) that the Org will have some continuity going forward.

      • MichiganGoat

        Shucks, thanks.

  • pfk

    I think he should indeed sign Wilken. Its nothing more than an insurance policy. This way if the new GM likes them they are on board. If not, they are let go with a buyout and will clearly catch on with another club. I don’t think its unethical at all and baseball people will totally relate to Ricketts’ predicament. He’s caught in a position of not having a new GM yet and 2 important contracts were coming up.

    • Cheryl

      Agree he should be resigned. Wilken could be given a bonus because of this year’s work and told that they have every intention of extending his contract after the new GM is hired. Still, I’d go ahead and sign him and extend his pfk says if holding off a month or two causes a problem..

  • NL_Cubs

    I can’t believe Ricketts would sign Fleita (and possibly Wilkens to follow) without talking with other owners and MLB execs and not understanding the risk/reward impact of such a decision prior to seating a GM.

    Good businessmen, particularly in a small, tight community such as MLB just don’t operate that way IMO.

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