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Halleck himself was never in a position to attack Lee.
When he was appointed General-in-Chief in July 1862, he summoned McClellan back to Washington and ordered him to attack Lee in the Shenandoah. Lee defeated part of the Union army before McClellan was able to reach the spot. Next came the unexpected Union win at Antietam, but Halleck and the whole of Lincoln's cabinet criticised McClellan for failing to pursue and destroy Lee's army, and McClellan was replaced.
Halleck then supervised the two further failed attacks on Lee (Fredericksburg and Chancellorsville), and the successful one at Gettysburg. The next campaign involving Lee was not till May 1864, by which time Halleck had been replaced.
What else can I help you with?
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