Given that Vicksburg commanded the water, and that it was practically impossible to come through the swamps and bayous that made up the Yazoo Delta, Grant decided to go down the other, meaning west, side of the Mississippi. He would then cross the big river and come at Vicksburg from its vulnerable, landward side. This sounded very good till one considered that there were practically no supplies on hand and that there was only one road running anywhere near the river on its western side. Moreover, how would Grant get his men from the western to the eastern side?

Admiral David Dixon Porter was confident, supremely so, about his ability to run past the Vicksburg batteries at night, but he warned Grant that it was a decision from which he could not reverse direction. The Mississippi current flowed at about six knots in that area, and to try to fight it, and the Confederate batteries on a return trip, would truly be hopeless. Therefore, it would be an all-or-nothing effort; Grant had always been a gambler, militarily speaking, and he decided to make the attempt.