Saturday "Morning" Cubs Thinks

Saturday "Morning" Cubs Thinks

Technically, anything before noon is “morning” so this will have to do.  I’ve been very tired slogging through this first semester of teaching and it shows:



Anyway, on with the thinks…

Numerous outlets reported that former Cubs pitcher Ryan Dempster, who I thought had retired earlier this year because he basically took the year off and told the Red Sox to keep their money in the final year of his contract, actually officially retired yesterday.  He did the one-day contract thing with the Chicago Cubs and was subsequently hired to be a special assistant to Theo Epstein and Jed Hoyer, which was spectacular timing since the Winter Meetings start on Monday.  Cubs Twitter was simultaneously amusing and reflective, with many folks remembering Dempster’s long run of solid pitching in Chicago and the various silly things that happened during his tenure, including the “oopsy” celebration, his bad Harry Caray impression, and the trade drama in 2012 that turned Randall Delgado into Kyle Hendricks (not complaining).

The narrative suggests that Ryan Dempster can help convince his former teammate on the Boston Red Sox, Jon Lester, to sign with the Cubs.  They did, after all, win a World Series in Dempster’s only season as a Red Sox, but to be perfectly frank, Dempster didn’t really help much in that campaign.  But I imagine that they formed a friendship, despite Dempster’s reputation among some fans of being annoying.  As a player, Dempster was actually fairly popular in my recollection, and he was involved in a lot of charities and community activities.  I assume that he will get a chance to do at least some of that in between doing the scouting and evaluating that special assistants do.

The Landmarks Commission approved the Cubs’ revised plan to switch up some of the outfield signage on Thursday, and for the conspiracy theorists out there, it seemed that the signs would now be arranged in such a way as to block only the rooftops that hadn’t caved to the Cubs’ demands.  As it is, the lawyer for the rooftops was particularly cranky during the hearing because the rooftops realize that despite their threats to sue and their much more publicized tensions since that hearing, the Cubs have all the leverage.  It sounds like the rooftops are bleeding money as the Cubs continue having their way, which almost reminds me of a tourniquet that is cutting off the circulation of money away from Wrigley Field.

First, the Cubs will have to beat the weather and Opening Day to complete the bleacher rebuild.  We’ll find out sooner than that which team Jon Lester will choose.


Please subscribe to our blogs (info here) and follow us on Facebook and Twitter!


Leave a comment
  • 1. It took me about 4 minutes to figure out the tweet. I guess you now have to go to Aquinas Wired's Chinese prison camp.

    2. Dempster was on with Bruce and Espo and admitted about as much. On the other hand, when they asked Kenny Williams about "a player from Notre Dame," he said "Isn't that unfortunate about Brandon Marshall's broken ribs and punctured lung?" Then said that it was Bruce's best attempt at suckering him.

    3. Does this mean that Dempster's Hall of Fame eligibility has been delayed one year?

    4. The Tribune had an article about the rooftop owners complaining that they were being squeezed out, but only hinted at the point both you and I figured out--the Cubs now have all the leverage.

  • As we wait where Lester signs, lets talk about will happen afterwards.....

    So many pitchers besides Lester than are on the market. Zimmermann, Kennedy, Colon, Jimenez, Hamels to name a few. Then there are the other free agent pitchers like Hammel, Shields, Masterson & Peavy that can help the Cubs.

    I think it is foolish to spend over $150 million for Lester for six or more years. Might be better to sign short term pitchers for far less money. Why make that terrible " I paid too much" mistake for one pitcher and be stuck with him.

    Maybe signing one of the two pitchers, Masterson / Hammel / Peavy, for the short term might be a better pay off for the Cubs.

    If Lester does sign somewhere else, then we can forget about signing Price who will be over $200 million in 2016.

    I am also against trading away the farm for a guy like Cole Hamels.

    So with the Winter Meetings happening this week, lets talk about who might get traded.

    Bryant, Soler, Russell, Baez will NOT be traded. Unless the name of Kershaw or Felix Hernandez is coming back from the other side.

    prospects who might be traded for pitching could be .....Vogelbach, Almora, Edwards, C. Villanueva, Beeler, Candelario, Black.

    If Lester does sign with the Cubs, then expect a T Wood trade and maybe a E Jax trade with prospects or other Cubs players.

    Starlin Castro is not going anywhere....for now. Other players that are in play for a trade could be ....Lake, Valbuena, Watkins, Alcantara, Straily, Parker, Rosscup.

    If there is a player I like to see Theo get, only if we can sign him for an extension, is Matt Weiters. Maybe we take Jimenez also from the Orioles. We can send Castillo, Lake, EJax back to the O's.

  • In reply to CubsTalk:

    The thing with blowing that much money on Lester is that the money actually is there and the short- and long-term impact of just that deal would be minimal given the financial flexibility they've built up. So they can suck up the risk here.

    I liked the idea of trading for Wieters but because he's about to become a free agent after this season, seems like a guy the Cubs would rather wait for unless the trade is favorable.

Leave a comment