I get that, they have been burned by bad contracts and some of them were not even that great of players over the years like Heyward, Soriano, Edwin Jackson, Chatwood, Fukudome, Milton Bradley, etc. But they need to be more heavy into that 2nd tier level contracts where you can get good return on guys with shorter and more reasonable deals that won't cripple you for 7 or more years if they flop.
The thing that frustrates me the most is the double talk by the ownership and front office denying that is is a full on rebuild when that is exactly what is it. They didn't make any splashes in free agency or trades in the offseason to give this team any chance to compete and it will become obvious by the deadline they are going to sell off any tradable asset that will bring back some value in prospects. You are going to have to pay Heyward what is left on his deal regardless and he has been garbage this year so they need to swallow their pride and DFA him as he's had plenty of consistent playing time over the years we know he is not going to get any better than he is now. Simmons has been useless too, he's only on a 1 year deal so not sure why he hasn't been DFA yet too but apparently they must think eventually he'll stop hitting weak grounders if they keep him around. There are guys at AA and AAA that you may as well start giving looks to as I would rather see the Cubs get their teeth kicked in playing them than guys that won't be around next year or the year after.