Scout from Pine Bluff to Simpson’s Plantation (December 27–28, 1864)

The December 27–28, 1864, scouting expedition from Pine Bluff to Simpson’s Plantation was undertaken to find cattle to feed the soldiers and civilians at the Union base at Pine Bluff (Jefferson County) but also involved several altercations with bushwhackers.

Captain Guernsey W. Davis of the Thirteenth Illinois Cavalry Regiment led 100 men from the Union garrison at Pine Bluff south from the base on December 27, 1864, “in search of beef cattle.” They soon encountered a group of bushwhackers who fled at the Federals’ approach.

Davis “ascertained” that three of the guerillas were Kit Flyn, James Bloom, and John T. Brent, and that “they, with others of the same profession, make a kind of headquarters” at the home of one of John Brent’s relatives. Davis arrested the latter Brent along with “another suspicious looking man found at his house” and sent them, along with a Confederate soldier whom the scouts had captured, to Pine Bluff aboard Union boats on the Arkansas River.

The Federal officer noted that Brent had denied seeing Flyn and the other bushwhackers “since his [Flyn’s] former capture”; he thus may have been the same as Private F. H. Flyn who was captured in the December 16, 1864, skirmish near Dudley Lake.

The Union troops rode another twenty miles before stopping for the night at Henry Simpson’s plantation. They headed back to Pine Bluff the next day, “driving cattle as we found them,” and as they neared McDaniel’s place in Richland Township, the advance troops saw a woman running from a house waving a hat, which led several men to flee to “an old gin-house in the field” as the Illinoisans approached.

Though the woman denied knowing of the men in the gin-house, Davis’s rear guard was fired on by five men located in the same area as the men who had run before the Federal advance. “The rear guard returned a few shots and the party fled back into the brush,” Davis reported; the party caused no injuries.

The scouting expedition returned to Pine Bluff, driving seventy-eight head of cattle before them, with Davis noting that “I prevented as far as possible the driving milch cows and work oxen.” Following Brigadier General Eugene A. Carr’s edict that payment receipts should be given to anyone from whom cattle were seized “unless…notorious rebels,” the Federal troops gave receipts totaling $442 to seven people for fifty-one cows weighing an approximate total of 11,050 pounds.

The two-day scout to Simpson’s Plantation not only highlighted the ongoing struggle to feed the population of the Union base at Pine Bluff, but also the ubiquitous presence of Confederate guerrillas in the countryside around the Jefferson County town.

For additional information:
The War of the Rebellion: A Compilation of the Official Records of the Union and Confederate Armies. Series 1, Vol. 41, part 1, pp. 977–978. Washington DC: Government Printing Office, 1893.

Mark K. Christ
Central Arkansas Library System