Original Word: שֵׁשַׁי
Part of Speech: Proper Name Masculine
Transliteration: Sheshay
Pronunciation: SHAY-shay
Phonetic Spelling: (shay-shah'-ee)
KJV: Sheshai
NASB: Sheshai
Word Origin: [probably for H8343 (שָׁשַׁי - Shashai)]

1. Sheshai, a Canaanite

Sheshai

Probably for Shashay; Sheshai, a Canaanite -- Sheshai.

see HEBREW Shashay

Word Origin
of uncertain derivation
Definition
a son of Anak
NASB Translation
Sheshai (3).

שֵׁשַׁי proper name, masculine a son of Anak (Aramaic form, compare GFM^Ju); — Numbers 13:22; Joshua 15:14 (both J E), Judges 1:10; Σες(ς)ει, Σουσαι, Σουσει.

שִׁשִּׁי, שִׁשִּׁים, שִׁשִּׁית see שֵׁשׁ below שׁדשׁ.

Biblical Occurrences

Sheshai appears three times in Scripture, always in connection with the Anakim of Hebron: Numbers 13:22; Joshua 15:14; Judges 1:10. In each verse he is named alongside his brothers Ahiman and Talmai. Numbers 13:22 introduces them as formidable inhabitants of Hebron discovered by the Israelite spies: “When they went up through the Negev, they came to Hebron, where Ahiman, Sheshai, and Talmai, the descendants of Anak, lived” (Berean Standard Bible). Joshua 15:14 recounts Caleb’s conquest of Hebron, and Judges 1:10 records Judah’s participation in the same victory.

Historical Background

Hebron, originally Kiriath-arba, was already ancient by the Exodus era, predating Zoan in Egypt (Numbers 13:22). Occupied by the Anakim—giant warriors whose very stature struck fear into Israel (Numbers 13:28, 33)—the city represented entrenched Canaanite power in the hill country. Sheshai, as one of Anak’s sons, embodied that intimidating presence. Yet Hebron also holds patriarchal significance: Abraham dwelt there, and the cave of Machpelah is located nearby (Genesis 23). Thus the Anakim controlled ground already promised to Abraham’s seed; their removal fulfilled both covenant and conquest.

Theological Significance

1. Fulfillment of Divine Promise: The expulsion of Sheshai and his brothers by Caleb illustrates the certainty of God’s oath to give the land to Israel (Genesis 15:18–21; Deuteronomy 1:36). What humanly appeared impossible—overcoming giants—proved entirely possible when the LORD fought for His people.
2. Vindication of Faith over Fear: Ten spies magnified the Anakim’s stature and minimized God’s power (Numbers 13:31–33). Caleb and Joshua trusted the promise instead. Decades later, Caleb personally drove out Sheshai, a living rebuttal to unbelief.
3. Typology of Spiritual Warfare: The Anakim prefigure formidable spiritual strongholds that confront believers. Caleb’s victory models persevering faith, reliance on God’s word, and patient endurance (Hebrews 6:12).

Character Study and Typology

Although no personal deeds of Sheshai are recorded beyond his occupation of Hebron and subsequent defeat, his name stands as a symbol for:
• Obstinate opposition to God’s people.
• Fleshly intimidation that must yield to obedient faith.
• The transient nature of worldly strength in contrast to the enduring kingdom purposes of God.

Lessons for Ministry

1. Giants still fall: Obstacles that appear insurmountable—cultural, ideological, or personal—cannot thwart God’s commission.
2. Wholehearted obedience receives inheritance: Caleb at eighty-five still “followed the LORD wholeheartedly” (Joshua 14:8–14). Ministry success is never age-bound.
3. Corporate cooperation: Judges 1:10 shows Judah joining Simeon to confront Hebron. Kingdom victories often require united action among believers.

Cross-References

• Genesis 23; 35:27 – Hebron’s patriarchal roots.
• Deuteronomy 9:1–3 – Assurance of victory over nations “greater and stronger than you.”
• 1 Samuel 17 – David’s triumph over Goliath, another giant, echoing Caleb’s earlier faith.
• 2 Corinthians 10:3–5 – Spiritual strongholds demolished by divine power.

Archaeological and Geographical Notes

Modern-day Hebron (Al-Khalil) lies about nineteen miles south-southwest of Jerusalem at roughly 3,000 feet elevation, a strategic height commanding southern Judah. Excavations reveal continuous Bronze and Iron Age occupation layers, corroborating its antiquity. While no direct inscription naming Sheshai has surfaced, large fortifications from the Late Bronze Age align with a city capable of housing warrior clans of extraordinary stature.

Summary

Sheshai, though only briefly mentioned, represents the imposing Anakite resistance confronted and overcome by faith-driven obedience. His demise under Caleb’s hand testifies that God keeps His promises, rewards steadfast trust, and empowers His people to inherit all He has pledged.

שֵׁשַׁ֣י שֵׁשַׁ֤י שֵׁשַׁ֥י ששי šê·šay šêšay sheShaiInterlinear Greek • Interlinear Hebrew • Strong's Numbers • Englishman's Greek Concordance • Englishman's Hebrew Concordance • Parallel Texts