Green’s Dictionary of Slang

(US) having worldly or criminal experience.

1950		Goldin et al. DAUL 118/2: Knock-around. Sophisticated, as a result of long underworld experience; belonging to or connected with the underworld. [...] Knock-around broad. Any girl belonging to, connected with, or experienced in the ways of the underworld [...] Knock-around ghee. Anyone belonging to, connected with, or experienced in the ways of the underworld.
1956		‘Toney Betts’ Across the Board 103: Knock-around guys shouldn’t do them things.
1975		E. Torres Carlito’s Way 9: I could take a knock-around broad but so long.
1985		N. Pileggi Wiseguy (2001) 64: She knew he was a knock-around guy.
2001		C. Stella Eddie’s World 45: An incident in a Queen’s Boulevard nightclub[...] changed him from a knock-around guy to a connected guy.
2010		Codella and Bennett Alphaville (2011) 29: The knock-around, mobbed-up guys I knew growing up were [..] just plain dumb.
2017		T. Pluck Bad Boy Boogie [ebook] ‘[A] knockaround guy who said he could call a hit on you in Rahway’.