What counter-arguments can be advanced against Socrates's claim that death is not to be feared in Apology 39a-42a?

Socrates's larger argument, that death is preferable to abandoning one's principles, is a matter of personal conviction, not some universal truth.

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Socrates says, as he awaits his own death, that death has to be one of two things: either it is "like being nothing, and the dead man has no perception of anything," or it is a "sort of change and migration of the soul" to another place.

The first proposition...

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Socrates says, as he awaits his own death, that death has to be one of two things: either it is "like being nothing, and the dead man has no perception of anything," or it is a "sort of change and migration of the soul" to another place.

The first proposition can be disputed on the grounds that life is good—that being human is about perceiving and feeling and that an end to that would be tragic, something to be dreaded. In short, if to die is really to sleep forever, it is hardly the self-evident good that Socrates attempts to portray it as. Some people could reasonably not see it that way.

His second possibility is even more contentious, for he is assuming that he will be judged after his death and that his judgment will result in his fellowship with other good men. In other words, he assumes that, if his soul survives his death and he is still conscious in the afterlife, that it will be pleasant. It assumes that the injustices of the world are not present in the afterlife, that "there is nothing bad for a good man" after death, and that the "gods are not without care for his troubles."

This is, of course, entirely a matter of faith on the part of Socrates and cannot be defended by any rational argument. Beyond that, Socrates is assuming that he is good, that his death is unjust, and that he will be rewarded. What if he is fairly judged to be a bad man, worthy of punishment in the afterlife? This thought does not seem to occur to him. Ultimately, his larger argument, that death is preferable to abandoning one's principles, is a matter of personal conviction, not some universal truth.

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Here as elsewhere, Socrates bases his argument on the assumption that nothing bad can befall a good man. In other words, a good man remains good whatever troubles he might endure throughout his life, yet this assumption seems questionable at best. A good man may not necessarily become evil due to his misfortunes, but that doesn't mean he isn't changed by them. Socrates seems to assume a rather crude dichotomy between good men and bad, which simply isn't validated by real-world experience.

He therefore assumes that applies here on earth also applies to the afterlife. Just as the soul of the good man in life may be changed by his experience of evil, so too may his soul undergo a profound transformation after death in ways that neither Socrates nor any mortal could possibly foresee. Socrates's unwarranted assumptions lead him to conclude that death will mean the end of all worldly troubles. As well as raising the question we've already discussed—whether a good man's soul is really able to remain unchanged in the face of evil—this assumption can also be challenged on the grounds that Socrates, contrary to what he and his acolytes might think, may not actually be a good man in any case. Surely that's a matter for the gods to decide, and no one on this earth can possibly interpret their will, no matter how skilled they may be in the arts of soothsaying or prophecy.

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The first counterargument you could advance is based on Socrates' assumption about the facts of the afterlife. He argues that either it is like a deep sleep and thus pleasant or that he will meet the famous dead and converse with them. He does not raise the possibility that he may go to an unpleasant afterlife.

The other possible counterargument is one that Plato puts in the mouth of Crito in the dialogue Crito, namely that Socrates' arguments are entirely selfish. Is Socrates shirking his duty to care for his wife and his children? By not arguing more strongly against his accusers (or perhaps accepting the help of the famous speech writer Lysias), did Socrates endanger his followers who had put there trust in him?

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