It's a gamble. I would have made the bet with odds (like you give $750 if the Cubs finish .500 or below, you get $1000 if they finish above). There are too many variables, too many young players who we don't know how long it will take them to adjust to bigs, injuries, the possibility of the Cubs starting off slow and Theo deciding to be sellers at the deadline one more time, etc. Nope. And that last part is definitely not happening. With Lester, I don't think he needs odds on that. I think he probably should give odds, if anything. Then again, teams never project for more than like 85 wins so what do I know. The fact that they will be relying on multiple players who "haven't done it yet" and that they have to be above .500 to win means no possible way should he be laying odds, with or without Lester. I still think they could easily be sellers if they have a rough start. These guys aren't going balls out to get to 82 wins. If Arrieta goes down and the team is scuffling, they won't hesitate to ditch a shot at .500 for a shot at a top ten pick. They will get the credibility they want with the Lester signing (reassuring season tickets holders and whoever they sign a tentative TV contract with) and will have much less to lose by losing in August and September.