撑死胆大的，饿死胆小的

撑死胆大的，饿死胆小的

Literally means:

the gutsy get stuffed while the gutless get starved

Actually means:

撑死 means stuffing someone to death, here means having a lot of money; 饿死 means starving someone to death, in this context means not being able to earn money.

This phrase means that the fearless can gain a lot of advantage or resources because they are reckless, even daring to do something illegal, while the timid cannot have anything, for they are always in caution, let alone doing anything beyond the bounds of their normal life.

It is often used to describe that where the legal system is not complete, or where the law enforcement is in mess, bad people tend to get out of control in amassing filthy riches, and in contrast, honest and law-abiding fellows are left in a disadvantageous situation.

撑死，此处指钱财很多;饿死，此处指赚不到钱。

撑死胆大的，饿死胆小的，指胆子大的人做事无所顾忌，甚至连违法的事都敢做，因而可以捞到很多好处或钱财，而胆子小的人做事谨慎，更不敢做越轨的事，什么好处都得不到。

常用来指法制不健全，法纪混乱，坏人胆大妄为，大发不义之财，相对而言则守法的老实人吃亏。