The term "Going Skippy on someone", refers to the action of someone stabbing a boss, or a person of higher rank in the back.

The term refers to an incident involving David Spade, were his assistant name "Skippy Malloy", suddenly and unpredictably attacked the actor in his own home with a taser.
"Damn, I see John always mumbling and clenching his fists every time he talks to the boss, it's kind of disturbing..."

"Yeah, everyone in the office thinks John's gonna end up Going Skippy on his ass..."
by Ecnel Ovelam October 24, 2011

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