I'm fine with all of this, and confused at why when Ellsbury took $153M 12 months ago we were all fine with it because we liked the player but hated the contract, but now so many think it was a messed up situation and a huge loss.
The difference in perception is that Boras was always going to take top dollar in free agency, and Lester wanted to come back at a discount. But I'm unclear where the missed opportunity/offer is.
I would have gone higher than 4/70 last off season, and maybe something like 5/100 would have gotten it done, but I would have hated 6/135 then. He had a whole year less of proving that his career was back on a dominant sustainable track (I'm still uncertain that 2014 isn't somewhat of an outlier on his overall trend line). So more than 4/70 is fine, but not a lot more.
Should we have signed him during the season? It was his choice not to negotiate, and going around that might not have continued the good will. But I suppose we could have said "we aren't negotiating, but wanted to throw out a 6/120 deal ready to sign if want" at the All Star break. I'm not sure he would have liked that or signed that, or if that would have been reinforcement that pitching well and waiting was increasing his value and waiting would be best.
Should we have gone 6/135 on the first day of free agency? I don't see any reason given the time they took now to think that a quick move would have gotten anything done. He was not in a rush. Maybe the Cubs wouldn't have been mentally prepared to make a blow you out of the water offer and we could have gotten him signed before the competition over bid. I still don't think so.
Should we have gone higher than 6/135? A lot of people seems to think that once you are there, what are a few more millions. But maybe that was a carefully calculated ceiling for the Red Sox in how much they thought he was worth optimistically, and rather than toy around in negotiations, they went right to their ceiling and made it clear they couldn't go up from there. If that is your ceiling, you don't go up more or you ensure you get the Winner's Curse that the Cubs have now ensured themselves.
In terms of what the Cubs actually got, maybe it nudges them onto competitiveness, and the overpay happens before the young players all reach arbitration, but it seems like a big risk. I don't buy that they are in it this year. They are a 73-win last place team who replaced Shark with Lester and will replace rookie call ups with sophomore slumps. I really like the 2016 Cubs, but I don't think they combine the run scoring and run prevention this season to do more than stay within sight of the second wild card.
So they waste the best value of Lester's contract on a potentially non-competitive 2015. I think it puts them in great shape for 2016 and 2017, but then by 2018 the contract starts to weigh just as they need the extra dollars to lock up their young hitters, and the results are that they can't improve the team elsewhere. If they go to the 2016 or 2017 World Series it likely is an overpay they can live with, and if they win it they won't have any regrets. But I still think this deal makes it tough to add more value to your ballclub then you pay for over the term.
Maybe a risk worth taking for a team that has waited 100 years, but one I'm glad the team with three shiny trophies avoided it. I wish Lester well and will miss him, but I have the same sigh of relief I did when Ellsbury left.