I just finished one of the most interesting books I've ever read. If you can get past the boring cover and equally boring title, I guarantee that this book is a roller coaster ride from start to finish.
In it, R’ Louis Jacobs presents a survey of a uniquely Jewish form of literature: the Responsa, otherwise known as the She'elos u'Teshuvos. From time immemorial, Jews have written letters to great (and less than great) Rabbis asking for their advice and guidance on every conceivable issue. While these questions generally pertained to matters of Halakhic practice, this book presents those that involved theological matters.
The book begins with the Gaonim in the 10th century and ends, with very few notable omissions, with the most recent Teshuvos written at the time this book was published (1975).
All in all, the book discusses well over 500 Teshuvos written by nearly 100 Rabbinic figures across 11 centuries.
Here are some of the Teshuvos that stood out to me:
In a question on whether one can bow respectfully to a Christian wearing a cross, the Terumas haDeshen (1390-1460) writes about a high-ranking Christian dignitary he knew as a young boy in Vienna who used to cover his cross whenever he saw a Jew in deference to their religious sensibilities.
The Maharit (1568-1639) discusses the case of a respected man in a community who admitted publicly that he had committed all three cardinal sins - he had been a highwayman who killed his victims, had slept with married women, and denied God. Among other fascinating things in that Teshuvah, the Maharit rules that although this man must confess his sins publicly, he must not confess the details of his adultery so as not to embarrass the adulterous women or their children.
On a similar note, the Noda b'Yehudah (1713-1793) discusses the case of a community Rabbi (unnamed to protect his reputation) who committed adultery with a certain married woman for three years and then married her daughter. He rules that this Rabbi must tell his father-in-law about what he did. A century later, the Divrei Chaim (1793-1876) and later the Ben Ish Chai (1835-1909) ruled the opposite, that an adulterer ought not to inform the woman's husband.
The Maharam Schick (1807-1879) discusses the case of a shul that demanded its rabbi (one of his students) remove the Mechitzah or else they would keep their businesses open on Shabbos. Maharam Schick instructs his student to remain firm. Several other cases of religious blackmail are also discussed in the book.
The Netziv (1816-1893) was asked whether one can sell their spiritual rewards in the world to come. A man with a great reputation for learning and piety sold a half share of his spiritual reward for a great sum, but that night the buyer had a dream where he was informed that the seller didn't amount to much in Heaven. Before explaining how it's not possible to make such a transaction and that the sale is invalid, the Netziv sardonically remarks that the very act of selling his spiritual reward proves his unworthiness in and of itself. Hai Gaon (939-1038) also has a shorter but similar Teshuvah.
In a remarkable Teshuvah, the Mateh Levi (1844-1910) was asked whether one ought to donate money to the building of a Church. He replied that not only is this not prohibited (provided that none of the Church goers are Jewish apostates) but that doing so constitutes a fulfillment of the great Mitzvah of Kiddush haShem. A contemporary of his, R' Dovid Tzvi Hoffmann (1843-1921), disagrees and says that one ought not to donate to a Church unless forced.
The Avnei Nezer (1838-1910) was asked whether a Baal Korei who was rumored of being a fornicator should be ousted from his position. He responds (sarcastically, I think) that not only is a mere rumor not enough to remove him from his post, but that the community ought to give this man a lot of money to invest in business and that would keep his mind off of sex.
If you ever wondered whether a brothel could be converted into a shul, the Machazeh Avraham (1847-1928) writes that although he can't find a specific objection in the Gemara or Halakhic literature, such a thing would be extremely offensive and distasteful and therefore he can't allow it.
There are literally dozens of other examples that stood out to me. I'm a huge fan of this book and highly recommend you check it out.
