Sirach 27:22–24

In three sharp verses, Ben Sira portrays the hypocritical flatterer whose outward sweetness conceals a calculating malice — a man who winks, smiles, praises, and then destroys. The passage moves from behavioral description to moral verdict, culminating in the stark declaration that both the sage and God himself hold such a person in contempt. These verses form a concentrated moral portrait of duplicity as a spiritual evil, not merely a social vice.

Verse 22 — The Winking Eye and Deliberate Distance

Ben Sira opens with a culturally loaded gesture: the wink (Hebrew qāraṣ, "to narrow or pinch the eyes"). This is not an innocent signal of familiarity; in the wisdom tradition (cf. Prov 6:13; 10:10), the winking eye is consistently associated with the plotting schemer — someone whose face performs one thing while the mind engineers another. The very physicality of the gesture matters: the body itself becomes an instrument of deception. The second half of the verse is equally precise — "those who know him will keep their distance." The Greek hoi ginōskontes auton implies not strangers, but those with experience of him. Ben Sira is describing social wisdom learned through painful familiarity. The double-tongued person is eventually unmasked, but only after damage is done. The wise response is deliberate avoidance — a prudential, not merely emotional, withdrawal.

Verse 23 — Sweet Speech as a Weapon

Verse 23 anatomizes the method of the hypocrite with clinical precision. The temporal contrast is the rhetorical hinge of the verse: when you are present he speaks sweetly (glukainei to stoma autou, "makes his mouth sweet") and admires your words — but afterward (meta tauta) he twists his speech (diastrephei to rhēma autou) and uses your own words as a snare. Ben Sira here anticipates what modern readers might call "intelligence gathering under the guise of friendship." The flatterer does not merely insult behind one's back; he weaponizes what was spoken in trust. The word "trap" (skandalon) carries particular resonance in the Greek tradition — it is the same word used for the stumbling block placed before the blind (Lev 19:14) and for spiritual ruin in the New Testament. The hypocrisy here is not passive dishonesty but active predation.

Verse 24 — A Double Condemnation

The final verse escalates dramatically from social observation to moral verdict. The sage steps out of the third person and speaks autobiographically: "I have hated many things, but nothing like him." This is a wisdom teacher wielding the rhetorical device of climax — after cataloguing many wrongs throughout his book, Ben Sira singles out the double-tongued hypocrite as uniquely contemptible. The Hebrew wisdom tradition reserves strong language about hatred precisely because it is not deployed casually. The final line — "The Lord will hate him" — is the theological capstone. This is not merely Ben Sira's personal revulsion transposed onto God; it is a claim grounded in the consistent biblical teaching that God, who is truth itself, is fundamentally opposed to deception (cf. Prov 12:22; Ps 5:6). The verse implicitly frames duplicity not as a personality flaw but as a theological offense — a violation of the divine order of speech, trust, and covenant fidelity.

Catholic tradition illuminates this passage on several interlocking levels.

On the nature of the tongue: The Catechism of the Catholic Church treats sins of speech with remarkable seriousness. CCC 2475–2487 identifies lying, flattery, and duplicity as violations of justice and charity that corrupt the social fabric — not merely private failings but sins against the community of truth in which human beings are called to live. CCC 2480 specifically warns against "flattery" (adulatio) as a grave fault when it confirms another in wrongdoing or serves one's own advantage. Ben Sira's hypocrite is the paradigmatic flatterer.

On integrity of speech: St. Augustine's treatise De Mendacio (On Lying) and Contra Mendacium (Against Lying) establish that any bifurcation between inward intention and outward expression violates the nature of the rational soul made in God's image. For Augustine, the lie is ontologically disordered because it sunders the word from the truth it is ordered to communicate. The hypocrite of Sirach 27 commits this offense with calculation and relish.

On God's hatred of duplicity: St. Thomas Aquinas in the Summa Theologiae (II-II, q. 111) treats simulation and dissimulation as species of lying, arguing that hypocrisy — presenting an exterior that contradicts the interior — is contrary to the virtue of truth (veritas), which obliges a person to make their outward presentation correspond to their inward reality. Aquinas notes that hypocrisy is especially grave because it corrupts the very signs by which human community is sustained.

On God as Truth: The declaration "The Lord will hate him" is grounded in God's own nature. Vatican I's Dei Filius (1870) and the Second Vatican Council's Dei Verbum §2 both underscore that God's self-revelation is an act of absolute truthfulness — God communicates himself without shadow of deception. The hypocrite thus places himself in radical opposition not merely to a moral rule but to the very being of God who is Veritas itself.

Ben Sira's portrait of the double-tongued man is searingly contemporary. In digital culture, the bifurcation between public persona and private intent has never been easier to maintain — a person can write warmly in a message thread while composing a denunciation in another window. The flattery Ben Sira describes has found new instruments in social media affirmation, professional networking performance, and the carefully curated "supportive" response that actually serves self-interest.

For the Catholic today, these verses offer three concrete applications. First, a call to self-examination: am I praising someone's work or words in their presence while undermining them elsewhere? The examination of conscience must extend to our digital communications. Second, a call to prudent discernment: Ben Sira does not counsel paranoia, but he does commend the wisdom of those who, having come to know the double-tongued person, keep their distance. Charity does not require continued vulnerability to a proven manipulator. Third, a call to cultivate integrity of speech as a spiritual discipline — letting what we say publicly match what we think privately, and choosing silence over flattery when we cannot speak truthfully. St. Francis de Sales in the Introduction to the Devout Life (III.30) identifies detraction and flattery as twin enemies of genuine charity and urges the devout soul to make their "yes mean yes."