After the brothers castigate Yehuda for not having advised them to return Yosef to his father, and instead suggested they sell him, they depose him from his position of leadership.

The Torah reports how in dejection Yehuda 'went down' from his brothers — both literally and figuratively — meeting up with Chirah.

He marries a daughter of a prominent merchant, and she bears him three sons.

He names his first son ער alluding to notion of עוררה — 'arousing' one's might, holding out hope that this child will bring forth the purpose of creation. (רמב"ן)

Yehuda takes Tamar as a wife for Er. Er dies prematurely for wasting his potential to father a child, out of fear a pregnancy would diminish her beauty.

Yehuda encourages the second son Onan, to take Tamar in fulfillment of the custom then to perform a levirate marriage. He too, ruins his capacity to allow a child to be conceived and dies in his iniquity.

Shelah, the third son, is withheld from marrying Tamar, as Yehuda fears that he too, may follow suit in his brothers' fate.

The frustrated Tamar in her sincere desire to be the mother of royalty disguises herself as a harlot. Not recognizing her, Yehuda is drawn to her but being empty-handed he promises to send her a kid of the goat later. She only consents if he leaves her an ערבון — pledge, to guarantee he will deliver on his promise. She requests the accoutrements of his status as nobility — his signet ring, his royal wrap, and the symbol of authority — his staff. (רמב"ן)

When Yehuda sends through his friend a kid of the goat to keep his promise and retrieve his pledge, she is nowhere to be found.

Through that union she became pregnant. Word spread that Tamar had committed harlotry and was with child. Yehuda sentenced her to be burnt. As she was being taken to her death she displays the ring, wrap, and staff, stating הכר נא — "recognize these items," revealing that to whomever these belong to is the one who impregnated her.

Yehuda awakens to the new reality, readily taking responsibility for his choice rather than denying, declaring, צדקה ממני — "she is more righteous than I," allowing her to live, eventually giving birth to twins, one of them destined to become the progenitor of the Mashiach. 

The Talmud mystically states that despite the troubles they were enduring as a family, with the sale of Yosef down to Egypt, and the terrible rift that existed in the family, it was within this event that the 'light of Mashiach' was being created.

What transition took place that catalyzed the hope for the future of our people?

There are two glaring parallels in this story with two other related episodes in this broader tale.

When Tamar procures the items of Yehuda's pledge, she states הכר נא — "recognize these items," echoing the words the brothers used — when they displayed the blood-stained tunic before Yaakov, deluding him into believing that Yosef was killed by a wild animal — saying הכר נא, "Identify, if you please, is it your son's tunic?"

Is this coincidental, or was she conveying a deeper message?

Tamar, knowing it was Yehuda, certainly did not need a guarantee to ensure that Yehuda would keep his promise.

Why did she insist on soliciting an ערבון — a pledge of these items specifically?

Ironically, much later in the story of the brothers, when Yaakov is reluctant to permit Binyamin to be taken down to Egypt, lest harm befall him, it was Yehuda who undertook the role of an ערב — guarantor, declaring before his father, אנכי אערבנו — "I will personally guarantee him."

It was this pledge and Yehuda's unwavering determination that indeed reunited the family.

What is the secret to this sequence of events that are clearly threaded together?

The Talmud discussing the role of an ערב — a guarantor, questions how is it possible that one can be bound by a commitment to guarantee a loan on behalf of the borrower?  Commitments must be implemented through the agency of an act of קנין — formal transaction. One takes a vessel or garment — often a handkerchief or yarmulka — from the party one is obligating himself to, and upon 'accepting' it 'gives' in return his commitment.

Yet when guaranteeing a loan, merely stating one is willing to before the loan takes place, concretizes the obligation.

The Talmud explains it with the following idea.

בההוא הנאה דקא מהימן ליה גמר ומשתעבד נפשיה — In consideration of the satisfaction that he is deemed trustworthy he obligates himself wholeheartedly.

We live in a world that lures us with its bait of happiness and success. After the sin of Adam and the breakdown of relationships, and the reality of temptation, man rationalizes his behavior with myriads of excuses and self-deceptions.

We have lost our trust in others and trust in ourselves.

There are moments when a person realizes he is being counted on to emulate G-d's trait of being the ultimate נאמן —trustworthy.

When one awakens to that reality — the need to be loyal, consistent, totally trustworthy, it is a moment of revelation that brings us back to the essence of man before the sin.

We recite each morning a series of blessings on Torah.

One paragraph begins, והערב נא — which is often translated as a request that the Torah should be sweet, tempting us to taste from it.

The teacher of Nachmanides, Rebbi Yehuda ben Rebbi Yakar, understands this blessing to be praying that the Torah within me should serve as my security, in my mouth and the mouths of your nation Israel, so that it shall never depart from my descendants, so that we shall all be יודעי שמך — who know Your Name. And knowing Your Name means to follow in Your ways…

Initially, Yehuda succumbed to the inclinations of man that are governed by selfish desires and deceptions.

When Tamar confronts Yehuda, she knows well his qualities of leadership, but she sought to teach him the lesson of נאמנות — unbending and unconditional loyalty to the will of G-d. By requesting his instruments of royalty, she was already plotting to present it to him in a moment of extreme challenge, when his reputation would be on the line, testing his נאמנות — his loyalty.

She conjures up his former moment of vulnerability when he rationalized the sale of Yosef and resorted to deception by presenting the blood-stained tunic.

With the same words ringing in his ear, הכר נא — do you recognize, she proverbially throws down the gauntlet of his 'accoutrements of royalty', challenging him to awaken to that higher awareness of absolute loyalty with no excuses, hoping he will cast aside self-interest, rising to his role of as the father of royalty, a king who will defined by his loyalty to his subjects with a total negation of self. Yehuda got it. In that moment the rays of Mashiach shined forth.

When later undertaking the role of ערב — the guarantor supreme, he lives up to his greatness, selflessly and confidently challenging without fear the 'viceroy', knowing that loyalty to the mission means there is no compromise or retreat. Nor fear for one's own welfare.

In the face of that clarity, Yosef submits in reverence to Yehuda, the paradigm king, knowing that the flaw that led to his journey was on the way to eternal repair.

It has been suggested that the word ערב — is a contraction of ער רב — greatly aroused and attentive.

A guarantor of G-d's will, will faithfully remain acutely aware of his responsibility, knowing that one is privileged to be the loyal guarantor of the Torah and G-d's will in this world.

באהבה,

צבי יהודה טייכמאן