Obama characterizes him, generally, as a loser, and yet he's the one (in the book, at least) who introduced Obama to what little there was of black "culture" in Honolulu -- taking an 11-12 year old to a bar frequented by hookers in the "red-light district," as well as taking him along to visits with Frank Davis. Stanley's also the one, according to O, who was so upset when Madelyn told him the story of the threatening black panhandler at the bus stop (for which she got thrown under the bus by Obama in his now-forgettable speech about race).
Stanley's a disturbing character -- he found his mother dead of suicide when he was eight, was known as tough guy in Kansas, marched across Europe with Patton's army without ever seeing battle in WWII (could any soldier have actually done that?), didn't seem able to settle down in one place for long until they reached Hawaii, and comes across as a white man obsessed with race, but totally devoted to his bi-racial grandson, who generally dismisses/ridicules him -- in the world according to Obama.
he certainly was.