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On May 5–6, 1864, during the Battle of the Wilderness, Robert E. Lee came closer than ever to crushing Ulysses S. Grant and the Union Army of the Potomac. Trapped in the burning forests of Virginia’s Wilderness, Grant’s 100,000+ men were disoriented, divided, and vulnerable. Lee deployed five key commanders—Richard S. Ewell, A. P. Hill, James Longstreet, and John B. Gordon—in a daring plan to split and destroy Grant’s army before it could fully concentrate. For a few critical hours on May 6th, 1864, it almost worked. Hill’s collapsing center was saved at the last second by Longstreet’s arrival. A hidden railroad flank attack nearly rolled up the Union line. Gordon’s dusk assault shattered the Union right. And then — hesitation, exhaustion, friendly fire, and missed opportunities changed everything. In this episode, we break down: • Lee’s high-risk trap in the Wilderness • Hancock’s devastating dawn assault • Longstreet’s brilliant flank attack — and his shocking wounding • Gordon’s near breakthrough at dusk • Why five Confederate generals failed to stop Grant’s relentless advance The Wilderness ended as a tactical draw — but strategically, it marked the beginning of the end for the Confederacy. Grant didn’t retreat. He moved south, launching the brutal Overland Campaign that would grind Lee’s army down through Spotsylvania, North Anna, and Cold Harbor. This is the story of the crossroads moment that changed the Civil War forever. #CivilWarHistory #BattleOfTheWilderness #OverlandCampaign