In his case going to prison isn't a deterrent. It is the punishment set by the law and is the path he chose (regardless of the circumstances that led to that decision.) You seem to have compassion for him so if you can safely share that with him then consider doing that because forgiveness can make a difference in people's lives. Many people have never been shown that kindness and sometimes it's enough to motivate a person to change their path.
Take into consideration that there are far too many people who have their paths severely limited for them. Also, just because it's the law doesn't make it right. Prison is a convenient way to brush problems under the rug and to allow the deterioration of social skills and a healthy mind and body to run rampant, for the soul to wither away. It's just that, convenient, and it doesn't do anything to solve the problem. If you want justice, educate people, otherwise "punishment" won't have any effect or significance if people never come to see anything wrong with their behavior/if the punishment never means anything to the individual because they see it as unwarranted, and thus they lash out, or because they simply don't care. Wasted time, wasted resources, and wasted human potential. I agree with your definition of fairness, and what you described doesn't exist, unfortunately, but I suppose that's why we have to strive towards making it reality rather than an ideal. There isn't enough rehabilitation offered, punishments are not appropriate and humane (prisons are noxious institutions, you cage an animal and see how their situation improves), and I believe that there is insufficient mercy.
I live in an incredibly damaged society that does little to actually help people,
especially given the resources it has, where the notion of a community of support has largely disintegrated, where fear and anger constantly threaten to (or actually do) overtake unity and understanding, and it's a damn shame. With how much I know humans are capable of doing, and with the resources at our disposal, it's a damn shame that we allow conditions to persist as they have. It's as if the humanity has been drained from many, and an emphasis on intense individualism (at the expense of the community) and greed has become the standard.
It isn't fair that someone would get better medical care here than someone else because they have more money, but it's true. They don't deserve it any more than the individual who's low-income, every life is of equal importance, but that's how our society is structured. It isn't fair that all the gains in wealth have gone disproportionately to extremely small fraction of the population while the majority works their asses off and makes far less than they deserve. Social and economic justice are constantly compromised because those in power naturally favor their own interests, which are the interests of the wealthy.
Fairness would be in a higher degree of self-autonomy and more power to shape policies, to have a voice in how one's life is forcibly shaped by external forces. A rule can't be fair if it neglects the voice of the people, if it indirectly serves to suppress social and personal advancement. In this country, it would be erroneous to say that "every man is born equal," because the vastly differing environments and unequal opportunities that abound change one person's prospects from birth. It shouldn't be that way, but it is.
Fairness, then, is also equal opportunity, which is in short supply.
