I think the sleaziest lawyer in Classic H50 was Tosaki, played by Kwan Hi Lim. In S04E18, Skinhead, he hassled the rape victim, bringing up the fact that she had sex with other men before she was raped, including with her boyfriend, who is present in the courtroom. The judge, played by Yankee Chang, warns Tosaki that he is "on thin ice."

This character also appeared during the Vashon episodes where he was a "fixer," sort of like Rudy Giuliani.

Ironically, Kwan Hi Lim was a judge (and presumably a lawyer) in real life. At the 1996 Five-O convention, James MacArthur said, "Kwan Hi Lim is a saint, he was the lawyer for my second divorce."

The reboot of H50 had an actor playing oily lawyers as well. In S01E16, E Malama (To Protect) one such lawyer was played by Michael Green, a real defense lawyer in Honolulu who described himself in a video on his WWW site as "dedicated" and "aggressive." Green also appeared as a different, but recurring, character in S03E08, Wahine'inoloa and S04E15, Wahine'inoloa.