This is a term that many people seem to be confused by, please read all of the previous examples to note the confusion. To understand this word you must focus on the word High. What has been lost is the origin of High Yella.
The term was originally High-Falutin Yella.
Well when the French ruled New Orleans there were many, many brothels and the highest priced was paid for the mixed African/European free prostitutes. It is well known that many slave owners raped their slaves and the children often escaped or were freed by the owners (how does one explain little mixed slaves running around the plantation)? This was not always a rule but many mixed slaves made up the population of free Africans in the colonies.
But. . . no matter how light, no matter how blue their eyes were, the High Yella's were still not allowed in the white community and in the black community with their perfumed skin, fine clothes and perhaps slightly uppity attitude the term High Falutin' Yella was coined.
"Damn, if Obama ain't a High Yella (High Yellow) I don't know who is!"