A new book claims Jewish scholars guided the Tudor king in his row with Rome
March 28, 2025 12:27It’s a familiar mnemonic to anyone who has ever had difficulty in remembering what happened to the six wives of Henry VIII: “Divorced, beheaded, died; divorced, beheaded… survived.”
What’s perhaps not so familiar to many is the role played by Jews in Henry’s efforts to divorce his first wife, Catherine of Aragon, so that he could marry the Tudor harpy Anne Boleyn. He grew sick of Anne, in the end, and when she failed to produce a male heir, concocted a dubious case of multiple adultery against her and had her beheaded.
Now the retired lawyer Jerry Rabow has written a dense but vastly entertaining book, Henry VIII and His Rabbis, which examines in forensic detail how Henry, in his desperation to marry Anne, sought Jewish advice to find a legal loophole to extradite himself from his marriage to Catherine.
It took six years of wheeling, dealing, bribery and backstage machinations – but despite all the foregoing, Henry was still not able to invoke Jewish law as a reason for obtain a divorce.
Even if anyone agreed that Deuteronomy trumped Leviticus, there was no one at Henry’s court to tell him the unpalatable truth: these strictures did not apply to Christians
Rabow, a lawyer from Encino, California, first became interested in Henry’s marital angst when he was working on his first book, Fifty Jewish Messiahs. He admits that he didn’t choose to write the Henry book. “It chose me. It pursued me over some decades,” he says.
He learnt that the pope at the time of Henry’s problems, the somewhat hapless Pope Clement VII, had entertained in his Vatican court at least two Jews who claimed to be the Messiah. The 16th century, it turns out, was littered with dodgy individuals insisting that they were the Messiah, only for it always to end in tears.
But Clement, who was absolutely determined not to give Henry an agreement that he should divorce Catherine, was enchanted by the Messianic pretenders David Reuveni and Shlomo Molkho – and they, in turn, played a pivotal role in a dispute between two leading rabbis in Italy, both of whom had been approached to secure a definitive get-out clause for Henry.
The central problem for Henry, according to Rabow, is that when he first decided to seek a divorce from Catherine, “he had no local Jewish community to consult”. Jews had been expelled from England in 1290 and were not formally allowed back until around 1656 under Oliver Cromwell.
Rabow acknowledges that there was probably a tiny group in Britain in Henry’s time, a handful of Sephardi Jews, living anxiously below the radar in order not to be noticed by the authorities.
For all intents and purposes, Henry, a staunch Catholic until his fight with Pope Clement, had to rely on Christians who had limited knowledge of Jewish law. Some, Rabow makes clear, had scholarly interchange with rabbis in Europe but “they were not mirror images. The Christian scholars were mainly interested in debating with Jewish thinkers for the purposes of converting them to Christianity. The Jewish scholars wanted to preserve their local Jewish community by remaining on good terms with Christian authorities.”
Divorce, as such, was not permitted in 16th-century England. Instead couples would seek an annulment, which meant obtaining a ruling that their marriage had been invalid. And it was on a legal question of this that the Henry/Catherine/Anne triangle rested.
Catherine of Aragon arrived in England in 1501 to marry not Henry, but his older brother, Prince Arthur. She was young, beautiful, fiercely Catholic and extremely popular with the public. But five months after their marriage, Arthur died of an unspecified condition. Rabow speculates it was from “the English sweating sickness”.
Seven years after Arthur’s death, Catherine and Henry married, having been given formal permission to do so – necessary because Henry was Catherine’s brother-in-law – by Pope Julius II, Clement’s predecessor.
From 1509 to 1533 Catherine and Henry remained married, but as Rabow reports, despite about seven pregnancies she only succeeded in successfully giving birth to one child, the girl who grew up to be Queen Mary. This, combined with Henry’s apparent insatiable passion for Anne Boleyn, made him desperate to be rid of his wife.
The problem was the interpretation of two biblical injunctions, one in Leviticus and one in Deuteronomy. The Leviticus verse said: “If a man marries his brother’s wife, it is an act of impurity. He has violated his brother, and the guilty couple will remain childless”.
Henry began to argue that he and Catherine had never been legally married, and that the “violation” had incurred Divine punishment, resulting in no male heir. But then came the Deuteronomy ruling, a loophole known as the “levirate” marriage. It meant that the brother of a man who died without children would be obligated to marry the widow. If he did not want to marry his late brother’s wife, there was a somewhat humiliating ceremony known as “chalitzah” in which she had to remove her brother-in-law’s shoe and then spit on the ground in front of him.
Needless to say, even if anyone agreed that Deuteronomy trumped Leviticus, there was no one at Henry’s court to tell him the unpalatable truth: these strictures did not apply to Christians.
Rabow paints a fascinating picture of the to-ing and fro-ing of Tudor courtiers, flitting between England and Italy, trying to find a compliant rabbi who would support Henry’s interpretation concerning his marriage to Catherine.
In 1530, an excited courtier reported that he had feedback from a physician/rabbi, Elijah Menahem Halfan, supporting Henry’s case. He also found support from a convert from Judaism to Christianity, former rabbi Mark Raphael, who, Rabow tells us, “became Henry’s most important and longest-serving authority on Jewish law and practice for the dispute”. Henry went so far as to bring Raphael to London in 1531, but once Raphael had advised the king that he could simply go ahead and take Anne Boleyn as his second wife – bigamy in Henry’s eyes – the king was outraged, and Raphael was discredited.
Also offering different kinds of advice to both Henry and Pope Clement were two other rabbis – Rabbi Jacob Mantino and Rabbi Jacob Rafael of Modena.
But Rabow makes it clear that it was impossible for Mantino and Halfan to have agreed on what became known as “the King’s Great Matter” because they were so fundamentally opposed – “locked in deep and permanent enmity”, says Rabow – over the fake Messiah, Shlomo Molkho.
And in the end, after six fruitless years of argument, and six years of hold-out from Anne Boleyn insisting that she would not be intimate with the king unless the couple were married and she was made queen – Anne fell pregnant, necessitating a hasty divorce and an equally hasty wedding.
Henry had made the scholar Thomas Cranmer archbishop of Canterbury, to near universal astonishment. Rabow writes: “Archbishop Cranmer was ready to use the authority of his new office to implement Henry’s wishes. On May 23, 1533… Cranmer annulled Henry’s marriage to Catherine. Five days later, Cranmer ruled that Henry’s previous private wedding to Anne Boleyn was valid and effective. Finally, on June 1, 1533, Archbishop Cranmer crowned Anne as Queen of England at a formal public ceremony at Westminster”.
Cranmer might have thought he knew on which side his bread was buttered – but he was later burnt at the stake in 1556 on the orders of Queen Mary… Catherine of Aragon’s daughter with Henry.
Henry VIII and His Rabbis by Jerry Rabow is published by Amberley Publishing