Modifiers matching shyster:

• resourceful,
• opportunistic,
• affable,
• unethical,
• optimistic,
• frank,
• cynical,
• alcoholic,
• manipulative,
• amoral,
• exploitative,
• witty,
• unscrupulous,
• shrewd,
• conniving,
• crafty,
• inept,
• incompetent,
• cunning,
• deceitful,
• wily,
• devious,
• materialistic,
• easy-going,
• psychopathic,
• quick-witted,
• Machiavellian,
• upbeat,
• entertaining,
• hugely-quotable,

Simple categories matching optimistic:

• shyster,
• child,
• poet,
• person,
• duck,
• director,
• warrior,
• lawyer,
• boxer,
• hero,
• philosopher,
• guru,
• lover,
• scholar,
• sidekick,
• soldier,
• billionaire,
• politician,
• writer,
• clown,
• invalid,