Howard was born in Baltimore and attended college in this city. He moved south, and worked as a newsdealer and then later as a lottery and policy dealer. When the Civil War broke out, Howard's business dealings were described as "obscure" according to a report in The New York Times. At a later point in his life, he claimed to have been a soldier for the confederate side for Tennessee, but this was subsequently disproven. In 1866, he was hired by the Kentucky lottery firm of C. H. Murray & Company to apply for a lottery charter in Louisiana from the state legislature. This effort failed, but after two years, a second attempt succeeded, partially as a result of bribery of key lawmakers in Louisiana. Howard was given $50,000 to apply for a charter and when the legislative grant came through, he refused to turn the charter over to his employers. A member of the firm of C. H. Murray & Co. named Marcus Cicero Stanley filed suit against Howard for being refused his "just share of the profits". The suit alleged that Howard had bribed a "large number of legislators" as well as an ex-Governor of Louisiana. But the lawsuit was dropped because it was decided that, given the nature of the gambling business, that the parties had no legal standing to enforce the contract.
