There are two main modes of moral reasoning. One of them is based around rules, and the other is based around relationships. The simplest version is process vs. outcome: Some people feel that justice has been done tolerably if the rules are followed and equally applied, while others feel that justice that rewards and punishments fall on the right heads.
These two different ways of looking at the world create a real moral and social (and political) chasm. E.g., Dana Goldstein and Jack Healy have written an essay in the New York Times based on the premise that paying to prepare your children for college applications is somehow morally equivalent to bribing admissions officers. To me, that seems like obvious moral illiteracy, but there are many people who see the world that way.
I tend to agree with Michael Oakeshott that ideology is for the most part reverse-engineered to suit preexisting preferences, and there seems to me some of that at work here, the arguing being: “Process-oriented models are inadequate in conditions of inequality, because some people have more resources to throw at the problem than others, which ensures inequality in competitive situations.” That is, of course, true, and it is true in contexts that matter a lot more than elite college admissions: If you get charged with a serious crime, you want a good lawyer, and those cost a lot of money.
The idea that the unequal distribution of money or other endowments renders morally perverse any system based on equally applicable rules is the stuff of Harrison Bergeron, an example of a modern error described by C. S. Lewis: selecting one truth from a body of moral truths and elevating it above the others as a kind of master-truth rather than engaging in the difficult and necessarily ad hoc business of relying on prudence and wisdom to balancing out things whose relative weight in any given context almost never is really self-evident.
Leaning too hard on the rules-based version of truth can produce outcomes that seem to us manifestly unjust: That’s the story of Les Misérables, in part, and it is why we have things like pardons and extraordinary clemency, as well as discretion in prosecution and sentencing. That the rules may produce imperfect outcomes is something we should expect and plan for—not something that should cause us to abandon the rules-based approach in toto. Leaning too hard on the relationship-oriented mode ends up as Lord of the Flies, Us-and-Them tribalism. And I think that’s partly what’s at work in the Times essay: The well-off and privileged need to be taken down a notch, even if that means attempting to create a crude and silly equivalence between paying bribe and enrolling your kids in SAT-prep classes that some people can’t afford.
The idea of a “level playing field” in the sense that the rules are applied to everybody equally is ordinary liberal rule-of-law stuff, the shortcomings of which we can deal with reasonably well through processes that are themselves also rule-constrained, e.g. pardon and parole procedures; the idea that a “level playing field” is meaningful only when naturally unequal endowments are forcibly made equal is fanaticism, and it is hostile to the organic quality of life in actual human societies as opposed to the ideological and utopian models of what those societies should look like.
Which is to say: If you really believe that society will never be just until it no longer is the case that some people have advantages relative to others, then you have no real alternative to Harrison Bergeron — and non-fiction totalitarian models of the familiar kind.