expression
person who never learns their lesson; persistent jerk
Used to describe someone, typically male, who repeatedly makes the same mistakes or misbehaves without showing remorse or improvement. Often carries a tone of exasperation or criticism.
また遅刻か。あいつは本当に懲りない奴だな。
Late again? That guy really never learns, does he.
何度注意しても同じ失敗をする。懲りない奴だ。
No matter how many times you warn him, he makes the same mistake. He's a persistent jerk.
The verb meaning 'to learn one's lesson' or 'to be chastened'. 懲りない is its negative form, meaning 'not learning one's lesson'.
A casual, often derogatory term for a person, usually male. 懲りない奴 combines this with the negative of 懲りる to form a set phrase.
A set phrase combining the negative form of the verb 懲りる (to learn one's lesson) with the casual noun 奴 (guy, person). The expression is straightforward and its meaning is transparent from its components.