Taking responsibility for another person's living property carries significant weight. When an animal is stolen from a guardian's watch, the guardian must face the consequences and compensate the owner. The primary approach among commentators is that this law deals with a paid guardian, contrasting with an unpaid guardian discussed in other contexts. Because the guardian receives payment for the work, there is an expectation to be extra alert and careful. Consequently, the guardian bears full responsibility in the event of a theft [מלבי״ם, ביאור יש״ר, בכור שור, חזקוני]. The law specifically uses the examples of an ox or a donkey because it is common practice to guard these animals for a fee, whereas items like money or tools are typically guarded without charge [מלבי״ם].
If the thief remains undiscovered, the guardian is required to pay the owner the value of the animal. However, if the thief is caught, the thief alone is obligated to pay double the value [קאסוטו]. While most commentators rely on traditional teachings to apply this strictly to paid guardians, an alternative perspective suggests that this liability extends even to an unpaid guardian. Because animals naturally wander and are highly susceptible to theft, anyone who assumes the responsibility of watching them is deemed negligent if they fail to prevent a theft, and therefore must pay [שד״ל].
The scope of the guardian's responsibility is deliberately broad, encompassing not only theft but also situations where the animal is simply lost [תורה תמימה, מלבי״ם, רש ר הירש]. This expansion stems from straightforward logic: if a guardian must pay for a theft, which resembles an unavoidable accident outside their control, they must certainly pay for a loss, which is much closer to direct negligence [תורה תמימה]. The concept of theft here also captures any secret disappearance, including instances where the animal wanders off and becomes lost on its own [רש ר הירש].
A paid guardian's responsibility is absolute, covering events that happen while they are absent or asleep. Even if the theft is carried out by a powerful force the guardian could not possibly overcome, payment is still required. The underlying assumption is that had the guardian been present and awake, the thieves might never have attempted the crime in the first place [רש ר הירש]. The disappearance of the animal from the guardian's possession is ultimately viewed as a direct result of their negligence [ביאור שטיינזלץ, קאסוטו].
The law precisely defines who carries this burden within a working chain of command. Liability falls specifically on the chief shepherd, who watches the flock either personally or alongside younger assistants. If the chief shepherd delegates the animal to the care of his young assistants and it is stolen, he is exempt from payment, as it is standard practice for a chief shepherd to entrust the flock to subordinates. However, if the animal is handed over to a different chief shepherd, who does not typically transfer guarding duties to others, the original liability to pay remains fully in effect [תורה תמימה, מלבי״ם].