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Having graduated first in his class from Howard Law School he was elected Monroe County judge over two white candidates in 1888. Governor Francis P. Fleming removed him from office in 1889 for marrying a black woman and a white man (although the groom said he was mulatto). Fleming replaced Dean with Angel De Lono, who was the first Hispanic judge elected in the Keys (Dean was said to be the first black county judge elected after reconstruction in Florida). Dean sued De Lono and argued his case against removal from office before the U.S. Supreme Court on September 13, 1891 to no avail. He left Key West penniless and disgraced, for Jacksonville where he died a pauper at age 59 in 1914. In 2002 Governor Jeb Bush reinstated his judgeship.