A profound turning point unfolds as a young man is handed over to strangers, setting in motion a chain of events that will ultimately draw an entire family down into Egypt. The narrative presents a complex web of actors—brothers, Ishmaelites, and Midianites—leaving the exact sequence of the sale open to deep exploration. The central mystery revolves around who actually pulled the youth from the pit and who executed the sale.
The primary approach among commentators suggests that the brothers themselves actively drew him up from the depths and sold him [רש״י, ספורנו, אור החיים]. However, an entirely different perspective argues that the brothers were completely unaware of the transaction. Having moved a distance away to eat and avoid hearing his cries, they were absent when passing Midianites stumbled upon the pit. According to this view, it was the Midianites who pulled him out and sold him to the Ishmaelites, while the brothers only discovered his absence later when Reuben returned. When the youth later confronts his brothers about selling him to Egypt, he either means they were the indirect cause by throwing him into the pit, or he mistakenly assumed they had orchestrated the sale [רשב״ם, שד״ל, רבנו בחיי, חזקוני, מלבי״ם].
The presence of both Midianites and Ishmaelites in the narrative raises questions about their respective roles. Some scholars view the two groups as part of the same extended family, descending from Keturah and Hagar, with their names used interchangeably [אבן עזרא, רד״ק, רלב״ג]. Others distinguish between them, explaining a division of labor: the Ishmaelites owned the caravans and funded the purchase but lacked expertise in the slave trade. The Midianites, acting as expert brokers, facilitated the deal, which is why the sale is attributed to both [ספורנו, אור החיים, תולדות יצחק]. A third perspective suggests this multiplicity of names reflects a tragic chain of successive sales, passing the youth from the brothers to the Ishmaelites, then to the Midianites, and finally to the Egyptians [רש״י, חזקוני, דעת זקנים].
This complex transfer creates an apparent contradiction later on when the Egyptian official Potiphar is said to have purchased him from the Ishmaelites, even though the Midianites brought him to Egypt. To resolve this, commentators explain that when Potiphar saw dark-skinned Midianites selling such a remarkably handsome, light-skinned youth, he suspected the boy had been kidnapped. Demanding security for the transaction, he required guarantors. The Ishmaelites stepped in to guarantee that the youth was not stolen property, and thus Potiphar is recorded as purchasing him from the legal guarantee of the Ishmaelites [חזקוני, הדר זקנים, רא״ש].
The transaction was finalized for a mere twenty pieces of silver. Such a low price for a handsome youth is attributed either to his face turning pale from the terror of snakes and scorpions in the pit, which diminished his market value [הדר זקנים, חזקוני, שפתי כהן], or simply because the sellers sought no profit, desiring only to be rid of him at any cost [ביאור יש״ר]. This specific sum resonates deeply in later Jewish law and practice. Twenty pieces of silver equate to five shekels. Because the youth was his mother's firstborn and was sold for this exact amount, God later established the Commandment to redeem a firstborn son for five shekels as a permanent atonement for this sale [רבנו בחיי, חזקוני, תורה תמימה]. Furthermore, dividing those twenty silver pieces among the brothers yielded exactly half a shekel each, forming the spiritual basis for the later Commandment to donate a half-shekel to the Tabernacle [תורה תמימה, הדר זקנים]. Even the physical act of pulling him from the pit serves as the legal foundation for the principle that ownership of an item is acquired through a physical act of pulling [תורה תמימה].
Stepping back, the entire sequence reveals a masterclass in Divine providence. The gradual distancing of the youth—from his own brothers, to distant relatives, and finally to foreign Egyptians—ensured his complete removal from Canaan. This journey fulfilled God's earlier decree of exile while simultaneously sending him ahead to build a survival infrastructure for his family's impending descent [גור אריה, ביאור יש״ר]. Yet, this bitter fraternal conflict and the resulting subjugation serve as a somber historical prototype. It stands as an early warning that internal strife and civil disputes within the nation of Israel inevitably pave the way for national subjugation and exile [ספורנו].