The generation that departed Egypt was destined to end their days in the wilderness following the failure of the spies. Out of that entire population, only a remnant earned the privilege of stepping into the Promised Land. Highlighting the specific names of these survivors emphasizes the profound reward granted for absolute loyalty to God and the strength to withstand immense social pressure. With the exception of Caleb and Joshua [ביאור שטיינזלץ], no one else from their peer group survived, as these two men remained entirely devoted to Him.
Caleb is identified by a dual title, referred to as the son of Jephunneh the Kenizzite. This combination raises a natural question regarding his ancestry: if his biological father was Jephunneh, why is he associated with Kenaz? The primary approach among commentators explains that Jephunneh was indeed his biological father. Following Jephunneh's death, Caleb's mother married a man named Kenaz. From this second marriage, Caleb's half-brother, Othniel the son of Kenaz, was born. Therefore, Caleb honors his biological father through the title "son of Jephunneh," while the Kenizzite title refers to his stepfather who raised him.
Identifying Caleb and Joshua as the sole survivors presents a historical difficulty, as another individual from that generation, Jair the son of Manasseh, also entered the land of Israel before eventually falling in battle at the city of Ai. To resolve this apparent contradiction, commentators explain that the decree of death in the wilderness did not apply to the entire nation indiscriminately. Rather, it targeted only men eligible for the army, specifically those between the ages of twenty and fifty. Jair was spared from this fate because he fell outside this age bracket, being either younger than twenty [פענח רזא, דעת זקנים, הדר זקנים] or older than fifty [חזקוני] at the time of the decree. Caleb and Joshua stand out because they were the only men from the military-aged population who merited entry into the land through their unwavering faithfulness.