Henry VIII’s Secret Mission to Rome: How He Went Behind Wolsey’s Back

Henry VIII’s secret mission to Rome in 1527 marked a dramatic turning point in both his personal life and English politics. As his marriage to Katherine of Aragon grew increasingly untenable and his relationship with Anne Boleyn intensified, Henry began to doubt Cardinal Wolsey’s ability—or willingness—to secure the annulment he so desperately wanted.

In a bold and highly confidential move, Henry bypassed his chief minister entirely, sending his trusted secretary William Knight on a covert diplomatic mission to the Pope. This secret effort to obtain a papal dispensation, hidden even from Wolsey himself, revealed Henry’s growing mistrust and marked the beginning of the Cardinal’s slow fall from grace. The mission may have failed in Rome, but it succeeded in reshaping the power dynamics at the English court.

Transcript of Henry VIII’s Secret Mission to Rome: The Plot That Even Wolsey Didn’t Know About

Today, we’re going to talk about Henry VIII’s secret mission—a covert diplomatic move that he deliberately hid from Cardinal Wolsey early on. As Henry pursued his divorce from Katherine of Aragon, he began to suspect that Wolsey might not be the best man for the job. So he launched a quiet diplomatic effort that completely skirted around Wolsey’s authority.

In September 1527, Henry VIII quietly sent his newly appointed secretary, William Knight, on a highly sensitive mission to Rome. It was so secret, in fact, that he explicitly ordered Knight not to inform Cardinal Wolsey—the very man who had, until then, controlled every detail of Henry’s diplomatic and religious affairs.

Knight’s mission was to secure a special dispensation from the Pope—one that would allow Henry to marry a woman whose sister he had previously slept with. It was a legal sleight of hand designed to undo his marriage to Katherine without challenging the validity of the original papal dispensation that had allowed that union. So why did Henry go behind Wolsey’s back?

By the autumn of 1527, Henry’s confidence in Wolsey was faltering. Despite more than 20 years of loyal service, the Cardinal had failed to deliver an annulment. Worse, Henry began to suspect that Wolsey’s loyalties leaned more toward Rome than toward the king’s personal desires.

His relationship with Anne Boleyn was growing more serious—Henry wasn’t just trying to escape Katherine anymore. He was planning a future with Anne. That meant action—not delays, excuses, or papal hesitation. So he made a secret move.

William Knight, newly appointed as secretary, was discreet and still operating under Wolsey’s radar. The instructions were incredibly specific: travel to Rome, but stop first in France—because Wolsey was in France at the time. Henry wanted Knight to lull the Cardinal and others into a false sense of normalcy.

Then, once in Italy, Knight was to request a papal dispensation—not for a divorce, but for remarriage on the basis of affinity: in other words, permission to marry a woman whose sister he had previously had relations with. The woman, of course, was Anne Boleyn. The sister was Mary Boleyn.

And so Knight did as instructed: he traveled first to France, where he stayed just long enough to maintain the illusion. Then he continued on to Rome, carrying with him one of the earliest—and most secret—moves in Henry’s campaign to remarry.

Then, once the coast seemed clear, he headed toward Rome—but it didn’t stay quiet for long. Rumors began swirling, and Wolsey got wind of the plan—perhaps through court gossip, perhaps through his network of informants.

Either way, Henry panicked. He blamed the leak on someone close to him and ordered Knight to take an entirely revised version of the document instead—one that was even more explicit and more confidential.

Henry instructed that the new dispensation be shown only to Pope Clement and his most trusted advisors. No one else—not Wolsey, not any other cardinal—was to see it. He even insisted that it be delivered only to men whom he was certain would “never disclose it to no man living, for any craft, the Cardinal or any other confined.”

But even with this new version, things didn’t go as planned. Knight struggled to gain access to the Pope. Political pressure in Rome was intense—Clement was essentially being held hostage by Emperor Charles V after the Sack of Rome. Granting any dispensation, especially one so clearly engineered, was extremely risky.

Knight alone couldn’t get the job done. So by December, Wolsey finally realized the scope of the situation. Knight’s mission had stalled, and the Boleyns were making end runs around him. So Wolsey inserted himself—but not by removing Knight. Instead, he brought in reinforcements.

He turned to Gregory di Casale, an Italian diplomat born in Rome who had lived for a time in England and was now stationed at the Vatican. Casale had the charm, the connections, and the political savvy to succeed where Knight had not. He used both diplomacy and bribery—offering 10,000 ducats and a 3,000 crown salary (more than some bishops earned) to help open the right doors.

Meanwhile, the Boleyns continued their own maneuvering. John Barlow, Anne’s chaplain and a fiery reformist, tracked Knight down in Parma and acted as a courier between Knight and the English court.

Around the same time, they also turned to Robert Wakefield, a Hebrew scholar from Cambridge fluent in Latin, Greek, and Aramaic. Wakefield argued forcefully that Henry’s marriage to Catherine violated divine law, not just church law, and that the Levitical prohibition was binding on Christians. It was precisely the sort of scriptural support Henry needed.

Crucially, Wakefield had been identified and promoted—not by Wolsey, but by Thomas Boleyn. Wolsey’s grip on power was slipping. Ambassadors like the Spanish ambassador, de Mendoza, were already reporting that Anne Boleyn had overtaken Wolsey’s influence. Mendoza even noted that Anne was answering the king’s summons for visitors—a role that Wolsey once controlled.

Reformers and evangelicals were also beginning to suffer under Wolsey’s harsh measures, including Robert Barnes, who had already been punished once for preaching. This time, he was imprisoned for distributing Tyndale’s banned New Testament—and then staged a dramatic escape, leaving a pile of clothes and a suicide note beside the River Nene, before joining Luther in exile.

So, Knight’s mission had ultimately failed. By early 1528, Pope Clement had fled Rome for Orvieto, and no formal decision was forthcoming. But the real result had already happened: Henry acted without Wolsey. Anne was asserting herself politically, and the entire operation—though unsuccessful in Rome—marked the beginning of Wolsey’s slow and irreversible fall.

By the way, that whole story of Robert Barnes I found fascinating. I just kind of skipped over it with one sentence. Unfortunately, the historical record is really sketchy on how he escaped, because he was supposedly in custody—and then he got out of custody, left this pile of clothes and a note saying he was ending his life, and slipped across the Channel.

He made it to Antwerp, and then all the way to Wittenberg, to Luther himself. But how he got out of custody to leave those clothes and that note is something historians still don’t know. At the time, the record was more concerned with painting him as a heretic and less concerned with how he managed to escape the authorities.

Some scholars suggest that he wasn’t locked in a high-security prison like the Tower. He might have been just under scrutiny somewhere—a more relaxed area of confinement, maybe at a university or a religious house in Cambridge. He was apparently in Cambridge at the time, and that might have allowed him a bit more movement—at least enough to slip away.

It’s also possible he had help. He still had supporters, and Cambridge was a major hotbed of reform. So people might have helped him—and it’s even possible the authorities were complicit, or at least indifferent.

That’s Robert Barnes—and of course, he escaped to Wittenberg and became something of a Protestant celebrity there. And so, the English government wasn’t exactly keen on broadcasting the details of how he got out—but he did. I find it fascinating.

So, that’s a little bit about these early political maneuverings that were happening around the time Henry stopped trusting Wolsey completely and tried to go around him a bit. It was also the earliest inkling for Wolsey that he might be starting to lose his grip on power.

Heather Teysko is the creator, writer, and producer of The Renaissance English History Podcast, the original Tudor history podcast, started in 2009. She's been writing about history online for over 25 years, since her first site on Colonial American history became number one in history on Yahoo in 1998. In 2019 she created Tudorcon, which is now a yearly event, in addition to writing books, and running TudorFair.com - a whimsical Tudor Merch shop.

She has been passionate about Tudor England since she first read Alison Weir's The Six Wives of Henry VIII 30 years ago, and subsequently moved to London after college to spend her time immersed in Tudor history (how exciting when she got to interview Alison for the first time!). In addition to history, she is passionate about travel, and has lived in 3 countries and 4 states (not counting her perpetual state of confusion), and her family (who help her host her YouTube channel occasionally).

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