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Herbert "Herb" Powell is the older half-brother of Homer Simpson. Illegitimately born to Abe Simpson and Gaby, he was raised by the Powell family and created immense wealth thanks to his car company.
The product of a short-lived affair between Homer's father, Abraham Simpson, and a female carnival worker, Herb was adopted by Edward Powell and Mililani Osler. He put himself through Harvard by working odd jobs because his adoptive parents refused to pay for his admission (or may not have been able to afford his college tuition). He then founded Powell Motors, a car company based in Detroit. Herb was overjoyed to learn that he had a birth family and bonded with his nieces and nephew, and - in his role as CEO - allowed Homer to design a car. However, Homer's car was a failure and it bankrupted the company. Herb ended up becoming a street vagrant. He prefers to be called "Unky Herb" by his nieces and nephew, because he thinks the term "uncle" is too formal.
He briefly settled in the Simpson household, despite his intense continuing antipathy toward Homer. Homer loaned Herb $2000 (from the power plant, as compensation for making him sterile from radiation), which Herb used to build an invention that translated infantile speech into comprehensible English, based on observations he made of Maggie Simpson. He proceeded to mass-produce his new product and regained his fortune. He then proceeded to pay back the Simpson family the $2,000, but also bought Homer a vibrating chair, Marge a new washer and dryer set, Bart a life membership in the National Rifle Association, Lisa a monthly set of classic novels, and a promise that he will buy something nice for Maggie. (It is also believed Herb did something for the Flanders family to show his gratitude to them for giving him a suit and not making look like a bum anymore). Most of all, Herb ends his antipathy towards Homer and is happy to call him his brother once again...
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