CSF77
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You can't go back in Cubs history and talk about who spent for what. Different ownership, different front office. That being said I believe they will overpay to get Lester but if they don't land him they won't overpay to get Shields. I can't see them even getting into the Scherzer derby where Scott Boras has set the opening bell at 7 years/$230 million. The most likely scenario is that they get Lester and also sign a mid tier guy out of the bunch of Masterson, Liriano, Brandon McCarthy or Ervin Santana with McCarthy or Masterson being most likely due to the lack of qualifying offers. I think they'll make a run at Martin but unless his market value ends up less than what everyone thinks they won't land him. They're not going to give him 5 years/$75 mil I don't think but the money is there and I could be wrong. Now the entire thing changes if the Yankees are really going to stay out of the top 3 pitcher market. If that's the case all of Boras' Scherzer bluster of 7/$230 is wasted on deaf ears because only the Yankees would even start a conversation there. So if they're out and Scherzer could be had for 6 years $175 I think the Cubs could very well bid on both he and Lester landing at least one. Or they could still focus on Lester, let Boston or Texas grab Scherzer leaving Shields who I could see them looking at if he'd sign in the 4 years $85 mil range. Bottom line I think the Cubs are going to spend $60-$70 million maybe a little less the chips don't fall their way. They're never going to spend like Anaheim, LA or NY. I don't see the payroll exceeding $110 million this year and then holding steady at around $120 mil until the TV contract kicks in around 2019 at which time they'll be signing their own guys. Still $60 plus mil buys you guys. If you figure Lester will sign for about $26-$27 mil per, 2nd tier guys at $9-$11 per, Martin at about $13-$15 per then you can see a clear path to what they want to do. In the non-Yankees scenario they could sign Scherzer at $28 mil per and Shields at $20 per without batting an eye. You have to watch the guys with qualifying offers, the money involved and who's bidding on whom before you can get a clear picture but the Cubs will spend.
You ned to paragraph this out more. Hard to follow your line of reasoning with the points all jumbled in a big paragraph.
That said yes I agree target 1 is Lester. Back up plan is Shields. Scherzer I doubt they will but the Cubs have a few players under Boras right now so there is a connection going in place.
I would put it as: Lester. Max they go 150 mil. Shields no more than 60 mil 3 years. 3rd option would trade for Cole Hamels.