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I saw this character in a Batman comic in either late 80's/early 90's. The character is a child or teenage crime boss who fancies himself a general/strategist; early in the comic Batman tries to "save him from thugs" only for the brat to hit him with a hammer when his (Batman's) back is turned.

Later, thinking he killed Batman, the crime boss addresses his goons and tells them Batman is dead (he's wrong of course, but doesn't know that yet) then interrogates two of Black Mask's men (who are both dressed up as clowns for some reason) and executes one for talking back at him.

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    Anarky? He often worked alone, but iirc he did rely on goons. dc.fandom.com/wiki/Anarky He is a teen wiz at strategy, who fancied himself as Batman’s intellectual equal. He was debuted in 1989 and active in 1990s.
    – Silly but True
    Commented Dec 2, 2021 at 18:39

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Ulysses Hadrian Armstrong, also known as the General and later the second Anarky, fits your description. He's a young military genius who first appeared in 1992, uniting Gotham's gangs as his own personal army during a three-issue arc in Detective Comics.

The General introducing himself.

The scenes you describe happen in the middle issue, Detective Comics #655. Batman saves the General when another gang leader drops him off a roof, re-opening a previous wound and allowing the General to hit him from behind:

The General striking Batman while his guard's down.

Later, he captures two of Black Mask's men and executes one:

The General interrogating and executing Black Mask's henchman.

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Could be Ulysses Hadrian Armstrong, known as The General. He later became the second Anarky.

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  • Much shorter, but 8 seconds quicker!
    – Paul D. Waite
    Commented Dec 2, 2021 at 22:08

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