Strong, where he remained, except for a brief absence, until he was called to the bar of New York City in 1827.
At the age of twenty, Stephens sought to satisfy his wanderlust by making a journey with a cousin to visit his aunt, who lived in Arkansas, then virtually a terra incognita. Having safely accomplished this visit, the two cousins decided not to return directly home and instead took a voyage down the Mississippi in a flatboat heading for New Orleans. After a few months Stephens returned from New Orleans by sea and resumed his study of law. He passed the bar examination in New York and practiced law there for eight years. He developed an ardent interest in politics, was a supporter of the Democratic Party, and gained a reputation as an occasional Tammany Hall speaker at Democratic Party meetings. He was noted for his strong advocacy of free trade and his strong opposition to monopolies. Stephens's earnest manner left no doubt of the courage of his convictions.
Stephens found the practice of law less than stimulating, however, and in the autumn of 1834 journeyed to Europe to improve his ill health.
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