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I think the biggest reason was Stuart's recent near-defeat at the battle of Brandy Station in early June. His cavalry was completely surprised by the yanks that they had ridden circles (literally in some cases) before and he had to save face and his honor by doing something spectacular. This led to Stuart's suggesting another ride around the Union army to Lee, who (demonstrating one of his few command faults) declined to give Stuart clear guidance. There was plenty of blame to go around. Hope that helps.
I disagree with this statement. He was doing what General Lee ordered him to do.