To go bankrupt a person has to go deep into dept that they cannot repay. This is generally something that can happen to rich people when they make extravagant investments or when something goes wrong in their business. Thus, it’s very hard for a bagger to end up bankrupt, but it’s not at all impossible for a bankrupt businessman end up a beggar.
People who have a lot to lose have a lot of worries, but if you are poor you might sleep better. The rich man contemplating financial disaster or about to take a major risk might quote this out of bravado, but only to focus his mind on the consequences of failure.