While searching for something else, I came upon a 1533 sermon from Luther in the eighteenth century Walch collection of Luther's writings:
I suspect most of the visitors here are not able to read German, especially in an old font! With the helpful use of AI, one can see a basic English translation:
Did you catch it? Luther once again says "sin boldly." Perhaps you're skeptical of an AI translation. Here's the English translation from The Complete Sermons of Martin Luther vol. 7, 140-141:
26. We also hear about this wicked servant that, after he had experienced grace at the hand of his king, he became proud and obstinate, stirring up the king's wrath once more. That's the way the godless world is which horribly misuses the doctrine of the forgiveness of sins. Some refuse to admit that their sins; even though they are wallowing in sin over their heads, yet they refuse to admit that they are sinners. For such people there is no forgiveness; for as we said earlier, if there is no sin, neither can there be forgiveness. Some keep right on sinning after receiving forgiveness, believing that the gospel allows everyone to do as he pleases. But the gospel is a message for the depressed, for the people with a guilty conscience, not for those who keep on defending their sins, nor is it for those who deliberately sin against a gracious God.
This English translation says, "keep right on sinning" rather than "sin boldly." Same thing. Here's how Google AI translates the phrase in question from the German text:
Conclusion
This is perhaps one of the clearest statements from Luther explaining what he means by "sin boldly." The statement isn't from an obscure private letter to someone struggling with scrupulosity over sin published long after his death. Rather, it is from a publicly preached sermon.... that was published during Luther's lifetime! There Luther lays out exactly what he means by "sin boldly." Rome's defenders need to be challenged to go deep into history. If you come across one of them using "sin boldly" confront them directly that they are maliciously spreading false information.
Addendum #1: Rome's Double Standard
The sentiment as it stands, and the interpretation attached to it by the rev. gentleman, forcibly remind us of the present teaching and practice of the Roman Church in their doctrine of "Penance," called a Sacrament, which I have already hinted at in a preceding page, and as an essential part of the Romish Sacramental system. Their catechism points out, "that there is no sin, however grievous, no crime however often repeated, which Penance does not remit,"(1) be the sin murder, fornication, adultery, incest, or sacrilege, (2) though a thousand times in every day we should commit fornication and adultery." I have shown that perfect repentance or "contrition" is not only not required in order to obtain remission of these sins in the Sacrament of Penance, but is declared to be absolutely a hindrance. This is effected by the absolution of the Priest, which follows the remission of the sin itself, and of the eternal punishment due to it, leaving a temporal punishment due, which can also be relieved by indulgences, and that indulgences extending to 10,000 or 20,000 years are specially reserved by the Popes for those who had "accustomed themselves to perjury and blasphemy almost every moment, and frequently committed murders, thefts, sacrileges, and adulteries." There is a remarkable similarity in the language as well as identity of sentiment. But Luther places faith in CHRIST, the Romanist places his faith in the PRIEST. The Roman Priest, in hearing sacramental confession and giving absolution, professes to represent the person of Christ himself!1 See "Catechism of the Council of Trent," Donovan's Translation, p. 278. Dublin, 1829.
2 Ibid., p. 278.
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