Glyndwr Michael didn’t make much of a mark in his lifetime. But once he was dead, he really stepped up.

Glyndwr was a tramp who died in London when he ingested rat poison. Shortly after his passing, he joined the Royal Marines and sailed by submarine to the southern coast of Spain, where he heroically influenced the Allied victory of WWII.

The operation I speak of was approved by no less than Winston Churchill and Dwight D. Eisenhower, and executed by British Intelligence. It involved borrowing Glyndwr from the morgue and dressing him up as the fictitious Captain William Martin. Various items were placed in Glyndwr’s pockets, including a photo of his imaginary girlfriend, Pam. But most importantly, Glyndwr carried correspondence between two British generals that suggested the Allies planned to invade Greece and Sardinia, with Sicily as merely the target of a feint.

Glyndwr was released from the submarine near the shores of Spain, where a local fisherman recovered the body. The Spanish government shared the discovered documents with German intelligence, who sent reinforcements to Greece and Sardinia, but none to Sicily, setting the stage for success in the Allied invasion of Sicily.

Now, you might be thinking to yourself, while there is never a bad time for a good espionage story, why is there one at the opening of a Rosh Hashanah essay? Certainly, there can be no correlation between this holiday and bold acts of deception.

Alas, there is.

Rosh Hashanah kicks off the annual trial of every Jew, determining our fate for the coming year. And in a crafty effort to influence the outcome, we deploy a string of bold acts of deception, designed to confuse the prosecuting angel into missing our court date and thereby inadvertently throwing the case.

We sound the shofar every day of the month of Elul, the month preceding Rosh Hashanah, to lead the prosecuting angel to believe the trial has gotten underway earlier than expected. We don’t sound the shofar on the morning preceding Rosh Hashanah, to lead the prosecuting angel to believe the trial has wrapped up.

Rosh Hashanah coincides with the start of the month of Tishrei, yet on the Shabbat preceding Rosh Hashanah we omit the customary prayers heralding the forthcoming new month, and on Rosh Hashanah we omit the prayers customary at the start of a new month—again, you guessed it, to wreak calendar confusion upon the prosecution.

And we delay rewinding the Torah back to the beginning with Bereishit until the end of the month of holidays, when logically it ought to be read at the outset of the new year, for the very same reason.

But, alas, our strategy is far from sound, as our prosecuting angel is not earthbound but heaven-found, and as such cannot be misled as to when Rosh Hashanah comes around.

So buckle up, as we’re about to explore a number of fascinating facets fueling our High Holiday season scheduling shenanigans.

Also during WWII, in the Pacific Theater where the Allies were battling the Japanese, the US Navy deployed a previously unheard of vessel, which, without ever firing a single shot, contributed meaningfully to a decisive victory.

The craft I am speaking of was an ice cream barge, capable of producing 10 gallons of ice cream every 7 minutes, and 500 gallons in a shift. During the prohibition era, ice cream had surged in popularity as an American treat and the ice cream barge raised morale amongst sailors by delivering large doses of deliciousness.

But it also played an important role in demoralizing the Japanese. The message it sent was that the Americans must really have the war under control if they can dedicate extensive resources to ice cream production.

And so it is in our war of wits with the prosecuting angel: We’re so confident of a positive verdict that we can forgo announcing the arrival of the new month, sounding the shofar on the eve of Rosh Hashanah, and drawing the inspiration associated with restarting the Torah from Bereishit. Our barrage of inaction can be compared to the ice cream barge, and our bullishness is too much for the prosecuting angel to bear, sending him into a tailspin of despair and depriving him of motivation to press his case.

But this explanation doesn’t compute. If our misdirection signals confidence in our spiritual perfection, the language used to describe it ought to allude to this dimension of inspiration and positivity as opposed to merely characterizing it as the exploitation of timeline uncertainty.

Which brings us to an inverse explanation: By failing to deploy the full array of spiritual tools at our disposal during this crucial moment of judgment, we signal to the prosecuting angel that our cause is a lost one and won’t necessitate a full court trial.

Yet this strategy appears to be faulty. A rudimentary cost-benefit analysis reveals that any profit incurred as a result of a loss of interest by the prosecutor is outweighed by the loss of Divine favor resulting from our neglect of essential rituals.

Which brings us to a fascinating twist.

What if it turns out that inaction is actually our most inspiring option?

To understand how this could be possible, we must explore the concept of extrinsic vs. intrinsic inspiration.

On Rosh Hashanah, we endeavor to bridge the gulf that has emerged between humankind and G‑d over the course of the prior year. This can be achieved by performing sacred actions or by stirring soulful emotions.

Were we to mark the new month, blast the shofar, and chant Bereishit, these righteous actions would fuel extrinsic inspiration, which would help us bridge our gap with G‑d.

Yet the realization that we’ve allowed our relationship with G‑d to slip away to the point where we are forced to run a no-mitzvah play in the hope of eluding prosecutorial sway triggers deep emotions that produce intrinsic inspiration, propelling us to bridge our divide with the Divine.

And it gets wilder still.

In addition to our inactions generating intrinsic inspiration, with the ancillary benefit of wreaking calendar confusion, there is furthermore the tertiary benefit of said inactions functionally factoring as actions.

This is because over time our annual repertoire of deceptions have been codified as Jewish customs. And so, our failure to show up in a variety of ways doesn’t signal our neglect of tradition, but our dutiful adherence to it.

Which reminds me of one of my favorite stories.

In the olden days, there were two brothers, named R. Zusha and R. Elimelech, who were great Chassidic Masters. At an early stage on their trajectory to vast renown, while disguised as beggars to keep a low profile, they once found themselves tossed in jail on fallacious charges.

On their first morning awakening in a cell filled with unsavory characters, R. Elimelech discovered his brother R. Zusha weeping silently. Asked why, R. Zusha explained there was a bucket in the corner that was serving as a latrine, which, in accordance with Jewish law, made it impossible for him to pray.

In an effort to comfort his brother, R. Elimelech posited as follows. We pray to connect with G‑d. Yet the same G‑d who invites us to connect with Him via prayer instructs us that under foul circumstances we mustn’t pray. So whereas ordinarily we connect with G‑d by praying to him, today we will connect with G‑d by not praying to him.

This unexpected perspective unleashed a storm of joy in R. Zusha’s heart. So relieved was he that his inaction constituted an action that he started to sing, following which he began to dance.

His fellow prisoners laughed uproariously at this scene, but soon their laughter morphed with Zusha’s melody and their feet were swept up by his ecstasy.

Sensing a disturbance, the warden came running. He shouted for an explanation, but his voice was drowned out by the jubilation. So he plucked a prisoner from the swirling circle and begged for clarification.

“It’s the Jews,” the prisoner exclaimed.

“But what inspired them?” the warden wondered.

“You’re not going to believe this,” the prisoner assured, “but it has something to do with the bucket.”

As any self-respecting antisemite knows, Jews must always be deprived of their joys. And so without further ado, the warden scooped up the bucket and whisked it from the cell. Noting this development, R. Elimelech turned to R. Zusha and gleefully exclaimed, “And now, my dear brother, you may pray.”

Inspired by Likkutei Sichot Vol. 24, pages 222-228.