I think the conditional is false. Forget about the death penalty for a moment. I can certainly think of examples in which one might conclude that a punishment that is "deserved" is nonetheless one that "ought not" to be imposed. First consider a CEO of some company who has seven children, a widowed mother whom he takes care of, and who has a total family income of $10,000,000 a year. But he embezzles $1,000,000 from his company and loses it gambling on the internet. It seems to me that a perfectly appropriate penalty for that crime, a penalty that is "deserved" is that, among other things, he be made to pay the money back. That is an appropriate kind of punishment for that kind of crime, and is thus "deserved."
But now consider a lower level manager at the same company who has embezzled $1,000,000 from the company, and lost it on the internet gambling. Having committed exactly the same kind of crime, he "deserves" the same kind of punishment for that crime. But now suppose that manager has seven children, a widowed mother whom he takes care of, and a total family income of $50,000. Even though he "deserves" it, imposing that sentence upon that person would make it impossible for him to fulfill other very important obligations to society, for example, sustaining his family, raising his kids, taking care of his widowed mother, because he would never be able to come out from under the weight of the punishment. Then it seems that judicial authority ought not impose that punishment on that man, even though it is "deserved". Yes, he has committed the same kind of crime. Yes, he "deserves" the same kind of punishment. But no, we ought not impose the same kind of punishment, since punishment must serve the common good.
In other words, imposing a particular penalty that is "deserved" might result in a much worse problem for society in some way. Then one ought not to impose it, but, rather, some other punishment that either meets the qualification of being equally "deserved" (a period of incarceration or house arrest for instance that does not lead to the destitution of his family or his inability to work), or a significant punishment that is also "deserved" but that nonetheless embodies a certain level of "forgiving the debt" that is owed. Recognizing that fact does not imply that he does not "deserve" to be made to pay back the money. It just implies that society need not punish someone in every way he could be punished according to what he "deserves". There may be many alternate ways to punish a crime, all of which taken singly count as "deserved"; in fact any punishment must be "deserved", even if we do not have recourse to it.
Or consider the Church's teaching on the death penalty. If we admit the extreme possibility contemplated by the Pope and the Catechism, namely, that there is no other way of protecting society, the act of putting to death must nonetheless be a punishment that the criminal "deserves". We cannot kill him even in such an extreme situation if he has not committed a crime for which that act of punishment is just "desert". We cannot kill him if his crime is stealing horses, for example, or embezzling money. If we suppose that he has committed a crime that does not "deserve" the act of being put to death as punishment, to say that suddenly he "deserves" it because we cannot protect society is to transform our failure into his "desert", which would be morally and politically reprehensible and perverse. Suppose when he is sentenced we can protect society, and so he is sentenced to life in prison without the possibility of parole because "his crime does not 'deserve' death as a penalty." But then through some societal wide disaster we become incapable of protecting society. Does he suddenly change from not "deserving" death as a penalty for his crime to "deserving" death as a penalty for his crime?
On the contrary, if one is to be put to death for a crime, it is a necessary condition that that act of punishment be a "just 'desert'" for that type of crime. No social need of protecting society can justify killing someone who does not "deserve" to die as punishment for what he has done. However, if there is some other way to protect society from someone who has committed a crime that "deserves" death, life in prison without parole for example, then the Pope exhorts us to use that other way. But again, insofar as life in prison without parole is an act of coercive punishment, that act of punishment must also be "deserved" as a punishment for that crime. So both acts, death and life in prison, are "deserved" as types of punishment for his crime. Yet we cannot do both. And we "ought not" to do one of them except in the most extreme case of not otherwise being able to protect society. If we put him to death, we are not suggesting that he did not "deserve" life in prison for his crime. Similarly, if we put him in prison for life because we "ought not" execute him, we are not saying that he did not "deserve" death for his crime.
Now consider this real case here and here. There are many people who think that if any heinous crime "deserves" the death penalty, killing a police officer certainly does. Policemen literally place their lives on the line for civil order and the common good. Their sacrifices are the means by which sufficient civil order is maintained such that we live in a society in which we need not have recourse to the death penalty. Without them, what the Pope writes is moot. In that case their lives "deserve" special protection in the law in order that one recognize the great sacrifice they are willing to make on a daily basis for the common good. Consistent with what the Pope teaches about the extreme situation in which one might have recourse to the death penalty, if they come under attack, the very means of protecting society, then it seems that death is certainly a penalty that is "deserved" for such an attack on civil order and the common good.
Supposing that to be the case, is it possible that someone may "deserve" the death penalty for what he has done, and yet society ought not to execute him? Well consider Ricky Ray Rector who killed a policeman. Governor Clinton left the campaign trail in 1992 to oversee his execution in Arkansas. Rector was not mentally deficient when he killed the policeman. But having killed him, he turned his gun upon himself and shot himself in the head. The subsequent brain surgery left him so mentally impaired that as he went off to his execution he saved his pecan pie from his last meal for "when he got back," and seeing Governor Clinton on television, said he intended to vote for him for president in the Fall. It is plausible to claim that given his mental competency in killing a policeman his crime was of a kind that "deserved" death as an act of punishment, and yet given his mental incompetency subsequent to his crime, he "ought not" to have been executed.
So what is going on here? That an act of punishment is "deserved" is a necessary condition for what society does to criminals. It is not a sufficient condition for doing something to a criminal. Nor is it necessary in the sense of "required."
This is a common moral phenomenon. One "deserves" to have returned to one one's property. A man asks me to hold his gun for him. It is his property. He "deserves" it back. But he is suicidal when he asks for it back. Then I "ought not" to give him what he "deserves". The discharging of such debts must serve the common good. The fact that there are circumstances in which, and goals for which we "ought not" discharge a debt that is "owed", doesn't imply that my friend doesn't in fact "deserve" his gun back. The fact of "desert" does not of itself imply the way in which such "desert" is to be discharged since any discharging of the "desert" must serve the good of the individuals involved and the common good. Just as there can be kinds of acts that are good that ought not to be done in particular (having sexual relations with one's wife (kind) on the courthouse steps (particular)) there are kinds of acts of punishment that are "deserved" and yet ought not to be done in particular.
The reason why an act of punishment can be both "deserved" and one we ought not to do is because like any act, it has many features that enter into its moral evaluation. If we distinguish between a) kinds of acts, b) the circumstances in which instances of those acts are to occur, and c) the goals for which instances of those acts occur, then we have to ask when we say that a "punishment is 'deserved'" what feature of an act of punishment we have in mind when we say so, a), b), or c)? It seems to me that there is certainly a sense in which the question of "desert" comes in to play with a). If a necessary condition for an act of punishment to be deserved is that it involves redressing the wrong at which it is directed, then one must ask of certain kinds of acts whether they are the kinds of acts that do in fact redress the wrong involved in the crime. To take an easy case, ten years of imprisonment, or hacking off a hand for stealing a loaf of bread would not be appropriate kinds of acts of punishment for redressing the wrong involved in the crime. Those kinds of acts would not be "deserved". Community service and a period of probation might be a kind of act that is deserved, but so might all sorts of limited others. But I would think at the very least, when talking about kinds of acts of punishment that are "deserved", one could never impose a kind of punishment that is not "deserved".
However, saying that such a kind of act is deserved does not entail that it is required. Take the death penalty. As a kind of act it may well be deserved for certain crimes, and yet it be the case that, as the Pope says, the only circumstance in which it is "required" is one in which there is no other way to protect society from the wrongdoer. (Given the fact that such an extreme circumstance is contemplated as possible, it follows from a) above that such a punishment must also be "deserved". One cannot use the death penalty to protect society even in an extreme situation, if that punishment is not also "deserved" qua redressing the wrong that was committed.)
In any case, when we bring in considerations of circumstances, that is, b), we might end up saying such things as that while a certain punishment is "deserved" it need not be required. In addition, we might even say that it is "deserved" but in certain circumstances we ought not to pursue it at all, as for example, if our means of carrying out the punishment are particularly brutal, or dehumanizing of the agents of the punishment, or that in these circumstances such a "deserved" kind of penalty would actually undermine the common good, or any number of other circumstances. Think of "truth and reconciliation commissions" throughout the world that are often used in lieu of judicial proceedings that might stand in the way of healing a brutalized society. Those who have brutalized the society certainly deserve punishment of some sort, and yet for the good of the society in the circumstances it is judged that they "ought not" to be so punished.
So with regard to b), I wouldn't think that b) bears upon "desert" but upon a prudential political and judicial judgment. Consistent with the point made above, any alternative punishment that might be imposed when making a prudential judgment about circumstances must be an act of punishment that is also "deserved". Life in prison without possibility of parole must be "deserved" if it is going to be used in such and such circumstances, rather than the death penalty. If it is not "deserved", one cannot impose it just to protect society from possible future harm. But given the brutality of our prison system, perhaps we ought not even impose life in prison without parole, but, rather, some limited time in prison, and so on. These are questions of prudence, not "desert".
I would say much the same about c) as b), namely, that here we have questions of prudence rather than "desert". One "ought not" to impose a punishment even if it meets a) as far as "desert" goes, and meets b) as for circumstances, if one is simply hoping to discharge and thus calm the blood lust of one's community, for example. And to pursue certain social goals, one can "forgive the debt" that is owed, and so on. But, of course, one can only forgive a debt that is actually "owed". It is neither forgiveness nor mercy to claim to forgive what is not "owed" or what is not "deserved". Such a claim is a kind of self deception on the part of governing authority.
Thus, insofar as there are cases in which one would judge that a punishment "ought not" to be employed and yet is deserved, it is clear that the conditional--if one ought not to employ some act of punishment to redress a wrong, then that act of punishment is not deserved--is false. Insofar as it has been explained above how such a state of affairs could obtain, we know why the conditional is false.
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