Between Wars
O'Hara was a firm believer in American expansion, in the form of filibustering. He joined others from Kentucky in an expedition to Cuba in 1850, after spending much of 1849 recruiting Kentuckians to the filibuster cause. Under the command of General Narciso López, O'Hara commanded a regiment, with the rank of colonel, in the hopes of removing Spanish rule from Cuba. In the battle of Cárdenas on May 18, 1850, he suffered a severe injury. After Lopez failed and died in his Cuba position in 1851, O'Hara returned to Kentucky, after fellow Kentuckians serving in Cuba took him with them as they escaped, returning to the United States at Key West, Florida.
O'Hara returned to journalism, first working for the Frankfort Yeoman of Frankfort, Kentucky, and then helping to found the original Louisville Times of Louisville, Kentucky in 1852, which became an organ for spreading Democratic Party propaganda. O'Hara left the Louisville Times in 1853 to join General John A. Quitman's filibuster expedition to Cuba. After Quitman's efforts failed, O'Hara attained a commission in the United States Army, was appointed captain of the Second Cavalry on March 3, 1855, and returned to Louisville as a recruiter for the Army. He was reassigned to Indian fighting on the prairies of Texas. On December 1, 1856, he was forced to resign by Robert E. Lee (then Lt. Colonel), as Lee brought up charges of drunkenness against O'Hara, and threatened him with court martial.
When John Forsyth Jr., editor-in-chief of the Mobile Register of Mobile, Alabama became minister to Mexico in 1856, O'Hara took his place in the newspaper. He continued to follow government orders, such as his diplomatic mission into the Tehuantepec grant debate. It has been speculated but never proven that he was involved with William Walker's filibuster expedition to Nicaragua.
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