Pleasants died on March 1, 1846, after participating in a duel with Thomas Ritchie, who was the editor of a rival newspaper, the Richmond Enquirer.

While Pleasants was able to open his own practice, his fear of public speaking and lack of conversational skills kept him from succeeding in the profession.

While Pleasants did lobby for the freeing of slaves he took issue with being called an abolitionist, a term that was seen as an insult in slaveholding states.

Some allege that Pleasants had loaded his pistol with blanks, as he had only wanted to frighten his opponent, while others state that he fired into the air.

Despite his early vehemence towards the other man, Ritchie was greatly remorseful for his actions and later left Pleasants's daughter a large sum of money in his will.