On Aug. 1, 1863, Judge Lewis Dent returned to Union lines, escorted by Confederate 1st Lt. Jesse Sparks. He was being exchanged under an agreement between Confederate general Paul Octave Hebert and Union general U.S. Grant. In return, a “civilian” staff officer was to be released to Hebert, as soon as the man could be returned from the Northern prison at Johnson’s Island.

Dent was a civilian, not a soldier, and though he often was referred to by the title, “Judge” – that was a leftover honor from when he was an attorney and legislator in California during its formative years. In Louisiana, sometime in the spring of 1863, he leased a plantation from the U.S. government, though this was not his only connection to the region. His wife was from Mississippi, and two of his uncles lived there, too.

It’s not clear when Dent was captured, though it may have been during Parson’s Raid in late June. He apparently became good friends with Hebert, though it is uncertain if they had known each other prior to the war, or formed their friendship while Dent was in Hebert’s custody. In any case, Hebert had bargained in good faith to exchange Dent for Maj. M.W. Sims, and on Aug. 1, all seemed to be proceeding as planned. Dent returned to his plantation and resumed operations. Military officials would criticize his work, condemning the conditions as excessively exploitative, though he would soon become a plantation commissioner, essentially gaining a promotion, supervising the leasing of plantations in the area.

Months passed, and summer turned to fall. By November of 1863, Sims had still not returned to Confederate lines. Hebert was beginning to worry, and queried Dent. Had Sims been released? Was he on his way? What had happened, and why the delay? Hebert asked Dent to investigate – not only because of their friendship, but also because Dent knew U.S. Grant personally. The general had married Julia Dent, Lewis’s sister.

Dent was probably as far in the dark as Hebert was, and it is not clear if he had any involvement in aiding Sims’s return to Confederate lines. However, after the war, Dent ran on the National Union Republican Party ticket for governor of Mississippi in 1869, and some supporters claimed he had “extended charity” to Confederate prisoners. One wonders if perhaps this is a reference to his aid to M.W. Sims or Gen. Hebert.

Dent lost his bid for the governorship, and died in 1874. At the special request of then-President U.S. Grant, former Confederate general Paul Octave Hebert served as a pall-bearer at his funeral.