### Core Meaning & Semantic Range
The Hebrew name **Sheshai**, represented by `{{H8344}}`, identifies a specific Canaanite figure. The name, which is probably for שָׁשַׁי, appears 3 times across 3 unique verses. In each instance, **Sheshai** is presented as part of a particular family group residing in Hebron.
### Biblical Occurrences & Contextual Analysis
The biblical narrative places **Sheshai** directly in the path of the Israelite conquest of Canaan. He is first mentioned when the spies sent by Moses `ascended {H5927}` and `came {H935}` to Hebron, where they found **Sheshai** along with Ahiman and Talmai, identified as "the children {H3211} of Anak {H6061}" [[Numbers 13:22]]. Following the initial exploration, Caleb `drove {H3423}` these same three sons of Anak from the land [[Joshua 15:14]]. The final account of **Sheshai** records that the men of Judah `slew {H5221}` him and his brothers in Hebron [[Judges 1:10]].
### Related Words & Concepts
The identity of **Sheshai** is always connected to a few key figures:
* `{{H289}}` **ʼĂchîyman** (Ahiman): Defined as "brother of a portion," Ahiman is always listed as one of the three Anakite brothers, alongside **Sheshai** and Talmai, who occupied Hebron ([[Numbers 13:22]], [[Joshua 15:14]]).
* `{{H8526}}` **Talmay** (Talmai): The third brother in the trio of Anakites. His story mirrors that of **Sheshai**, being seen by the spies, expelled by Caleb, and ultimately killed by the tribe of Judah [[Judges 1:10]].
* `{{H6061}}` **ʻÂnâq** (Anak): The progenitor of the clan. **Sheshai** and his brothers are explicitly referred to as the `children {H3211}` or sons of **Anak**, establishing their lineage as formidable Canaanites ([[Numbers 13:22]], [[Joshua 15:14]]).
### Theological Significance
The role of **Sheshai** is significant within the context of Israel's conquest.
* **Embodiment of Opposition:** As one of the children of Anak, **Sheshai** represents the powerful inhabitants the Israelites were afraid of and commanded to dispossess. Their presence in Hebron was a primary obstacle to taking the land [[Numbers 13:22]].
* **Fulfillment of Conquest:** The actions taken against **Sheshai** directly illustrate the fulfillment of the command to possess the land. He was first `drove out {H3423}` by Caleb and later `slew {H5221}` by Judah, with these verbs signifying dispossession and destruction ([[Joshua 15:14]], [[Judges 1:10]]).
* **Symbol of Overcome Fear:** The Anakim were a source of great fear, prompting the question, "Who can stand before the children of Anak!" [[Deuteronomy 9:2]]. The defeat of **Sheshai** and his brothers by Caleb and Judah serves as a testament to their eventual victory.
### Summary
In summary, `{{H8344}}` **Sheshai** is a figure whose importance is tied entirely to his identity as an Anakite in Hebron. He is never mentioned alone, but always with his brothers Ahiman and Talmai. His narrative arc—from being a feared inhabitant to a defeated foe—functions as a concise and potent example of the biblical account of the Israelite conquest of the promised land.
TRV