Yaakov's essential bond to Hashem through the bris

במדרש עשו אחי איש שעיר שמתלכלך בעונות ואין לו במה להתכפר.

In the Midrash: "Esav my brother is a hairy man (ish sa'ir)" — that he becomes soiled with sins and has no means by which to gain atonement.

The Midrash reads Yaakov's words as a contrast: Esav is "hairy," stained by aveiros, with no avenue available to him for kapparah.

ואנכי איש חלק שיש לי במה להתכפר ולהתכבס.

"And I am a smooth man (ish chalak)" — that I have a means by which to gain atonement and to be cleansed.

Yaakov, "smooth," does have a path to kapparah, a way to wash away whatever stain may cling to him.

ד"א איש חלק חלק ה' עמו.

Another interpretation: "ish chalak" — "the portion (chelek) of Hashem is His people."

A second reading of "chalak" links it to "chelek": Yaakov is the very portion of Hashem.

כבר כתבתי במ"א כי ב' הפירושים אחד הם לפי שיש בו דביקות בעצם באלקות מצד ברית מילה.

I have already written elsewhere that the two interpretations are really one, for he has an essential attachment (deveikus) to the Divine by virtue of the bris milah.

The two readings of "chalak" merge: Yaakov can be cleansed precisely because he is Hashem's "chelek," bound to Him essentially through the bris milah.

לכן אין העונות נדבקין בו בעצם רק במקרה.

Therefore the sins do not cling to him essentially (be'etzem), but only incidentally (be'mikreh).

Because his bond with Hashem is intrinsic, any sin remains external and accidental — it never penetrates his true essence.

לכן מתכבס במהרה.

Therefore he is cleansed quickly.

Since the stain is only superficial, it can be washed away with ease.

ועשו איש שעיר שערות הם המותרות.

And Esav is "ish sa'ir" — hair represents the surplus matter (mosaros).

Esav's hairiness symbolizes the excess, waste matter of the body — that which has no inner holiness.

ועיקר מותרות הגוף הוא הערלה שניתוסף ע"י החטא.

And the primary surplus of the body is the orlah (foreskin), which was added through the sin.

The chief example of this superfluous matter is the orlah, an excess that entered the body as a consequence of the original sin.

לכן מתדבק בו החטא שא"י להתכבס.

Therefore sin clings to him in a way that cannot be washed off.

Because Esav remains in the state of "orlah," sin attaches to his very essence and cannot be cleansed.

וגם פי' המדרש איש שעיר גבר שידין כי הרוחות ושדים נתדבקו בערלה.

And the Midrash also explains "ish sa'ir" as "a man of demons (sheidim)," for the spirits and demons attach themselves to the orlah.

The Midrash reads "sa'ir" as alluding to demons, since the forces of impurity cling to the uncircumcised state of the orlah.

לכן ונשא עונותם איש תם שנולד מהול ומתכבס מן העונות ונותנו לאיש שעיר:

Therefore "he shall bear their sins" — the "ish tam" (wholesome man, i.e. Yaakov, who is associated with one born already circumcised) is cleansed of the sins and places them upon the "ish sa'ir."

Like the sa'ir la'azazel that bore Yisrael's sins, the "wholesome" Yaakov — essentially pure as one born mahul — sheds his incidental sins onto Esav, the "ish sa'ir."

Summary: Reading Yaakov's "I am a smooth man" together with "the portion of Hashem is His people," the Sefas Emes teaches that Yaakov's essential deveikus to Hashem through the bris milah means sin clings to him only incidentally and is quickly washed away. Esav, the "hairy man," embodies the body's surplus — the orlah added by sin — to which impurity and sin attach essentially, so that the wholesome Yaakov can shed his incidental sins onto the "ish sa'ir."