General Gregg in Raymond receives word that the main Federal force is approaching Edwards, Mississippi. But he also knows, finally, that there are Federal troops approaching his own position. He logically assumes this latter group must be a mere raiding party. Just after dawn he parades his men through town and conceals them in fields at the edge of Fourteen Mile creek, with 35 men picketed on the bridge over the creek itself. When the Federal raiding party charges across the bridge Gregg intends to pin them against the river with a furious and overwhelming charge of his own.
Just as Gregg expects, about 10AM, Federal skirmishers appear at the tree line South of Fourteen mile creek. But to his surprise they are supported by Union artillery, which begins to shell his picket guard with canister. Clearly this is more than a mere raiding party. But Gregg now assumes it is merely a brigade. So he moves his 3,000 men out of canister range behind some low hills, where they can remain hidden, ready to fall upon the Union Brigade after it crosses the bridge. Gregg also moves two regiments into woods to his left where they can quickly slip across the creek and capture the Union artillery.
What Gregg does not know it that he is facing General John Alexander “Black Jack” Logan’s entire Third Division, advance guard for McPherson’s 17th. Corps of 16,000 men. Logan may look like a wild man with his intense jet black eyes and tosseled hair but he is a surprisingly good soldier - even if he is yet another of those Stephen Douglas Democratic generals. But the difference between the political generals Logan and McClernand, is that Logan is a charismatic leader of men with no dreams of higher command. And he smells Gregg’s trap to his front. Logan allows his men to take a meal break while he posts cavalry on his flanks.
It is after noon before Logan orders his men to advance. But what follows would be a comedy of errors if men were not dieing. On the Union right the 23rd Indiana regiment crosses Fourteen Mile Creek above the bridge, and stumbles sideways into a Texas Regiment that punishes the Hoosiers and sends their survivors scampering into retreat back the way they came. Then the Texans charge across the creek and are caught in a cross fire between an Ohio and an Illinois regiments. They also fall back in retreat. On the opposite flank, the two Confederate regiments step out of concealment to discover what looks like the entire Federal Army in line of battle in front of them, with another two full Union Regiments outflanking the rebel position at that very moment. In a flash the tables have been turned, and suddenly it is the Confederates who had been suckered into attacking a far superior force. The best that Gregg can now do is to fight a series of desperate delaying actions while he withdraws, covered by the Third Kentucky Mounted Infantry which has just arrived from Jackson. Raymond is abandoned as Gregg falls back on the Mississippi capital.
The Union casualties at this "Battle of Raymond" are 68 killed, 341 wounded, and 37 missing. Rebel losses are reported as 100 killed, 305 wounded, and 415 captured. But the Union Army reports burying many more Rebel dead than the 100 officially listed, indicating the almost haphazard nature of the force that was quickly thrown together at Raymond. McPherson senses this and notifies Grant.
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