You know, I used to think it was awful that life was so unfair. Then I thought, wouldn't it be much worse if life were fair, and all the terrible things that happen to us come because we actually deserve them? So, now I take great comfort in the general hostility and unfairness of the universe.

Life is unfair. Death is unfair.

The most unfair thing about life is the way it ends. I mean, life is tough. It takes up a lot of your time. What do you get at the end of it? A Death! What’s that, a bonus? I think the life cycle is all backwards. You should die first; get it out of the way. Then you live in an old age home. You get kicked out when you’re too young, you get a gold watch, you go to work. You work forty years until you’re young enough to enjoy your retirement. You do drugs, alcohol, you party, you get ready for high school. You go to grade school, you become a kid, you play, you have no responsibilities, you become a little baby, you go back into the womb, you spend your last nine months floating …and you finish off as an orgasm.

La fortune ne paraît jamais si aveugle qu’à ceux à qui elle ne fait pas de bien.

From time to time in the years to come, I hope you will be treated unfairly, so that you will come to know the value of justice. I hope that you will suffer betrayal because that will teach you the importance of loyalty. Sorry to say, but I hope you will be lonely from time to time so that you don’t take friends for granted. I wish you bad luck, again, from time to time so that you will be conscious of the role of chance in life and understand that your success is not completely deserved and that the failure of others is not completely deserved either. And when you lose, as you will from time to time, I hope every now and then, your opponent will gloat over your failure. It is a way for you to understand the importance of sportsmanship. I hope you’ll be ignored so you know the importance of listening to others, and I hope you will have just enough pain to learn compassion. Whether I wish these things or not, they’re going to happen. And whether you benefit from them or not will depend upon your ability to see the message in your misfortunes.

Misfortune is not fair, fate is not just, but they exist just the same.

...but think how mysterious and often unaccountable it is — that lottery of life which gives to this man the purple and fine linen, and sends to the other rags for garments and dogs for comforters.

Our system of justice should reflect an understanding that any of us could have been dealt a very different hand in life. In fact, it seems immoral not to recognize just how much luck is involved in morality itself.

People don't always get what they deserve in this world.

Mankind accepts good fortune as his due, but when bad occurs, he thinks it was aimed at him, done to him, a hex, a curse, a punishment by his deity for some transgression, as though his god were a petty storekeeper, counting up the day's receipts.

There will always exist inequalities which will appear unjust to those who suffer from them, disappointments which will appear unmerited, and strokes of misfortune which those hit have not deserved. But when these things occur in a society which is consciously directed, the way in which people will react will be very different from what it is when they are nobody's conscious choice.

We grossly overestimate the length of the effect of misfortune on our lives. You think that the loss of your fortune or current position will be devastating, but you are probably wrong. More likely, you will adapt to anything, as you probably did after past misfortunes.

Talk about how various people have been “winners” in “the lottery of life” or have things that others don’t have just because they “happen to have money” is part of the delegitimizing of property as a prelude to seizing it.
Luck certainly plays a very large role in all our lives. But we need to be very clear about what that role is. Very few people just “happen” to have money. Typically, they have it because their fellow human beings have voluntarily paid them for providing some goods or services, which are valued more than the money that is paid for them. It is not a zero-sum game. Both sides are better off because of it — and the whole society is better off when such transactions take place freely among free and independent people.
Who can better decide the value of the goods and services that someone has produced than the people who actually use those goods and services — and pay for them with their own hard-earned money?
Luck may well have played a role in enabling some people to provide valuable goods and services. Others might have been able to do the same if they had been raised by better parents, taught in better schools or chanced upon someone who pointed them in the right direction. But you are not going to change that by confiscating the fruits of productivity. All you are likely to do is reduce that productivity and undermine the virtues and attitudes that create prosperity and make a free society possible.

The cult of individuals is always, in my view, unjustified. To be sure, nature distributes her gifts unevenly among her children. But there are plenty of the well-endowed, thank God, and I am firmly convinced that most of them live quiet, unobtrusive lives. It strikes me as unfair, and even in bad taste, to select a few of them for boundless admiration, attributing superhuman powers of mind and character to them. This has been my fate, and the contrast between the popular estimate of my powers and achievements and the reality is simply grotesque.