First, Lee had put all his brigade & divisional commanders under strict orders NOT to engage the enemy. The fact that AP Hill, and Henry Heth (the corps & divisonal commanders that started the skirmish respectively) weren't flogged and court martialed afterwards is amazing.
Anyway, in the first day, the CSA could have and should have won it outright. When the Union cavalry pickets finally did break, the CSA had some tremendous, though short lived, tactical advantages. However, for some reason, Old Baldy, Robert Ewell, decided to hold up at Cemetary Hill and would not press the attack. Had he, O.O. Howard's 12th corps almost certainly would have been overrun, putting Ewell on Hancock's 1st corps rear flank. The Union would have had to have withdrawn. Instead, Ewell ordered Early and company to hold up, allowing Sedgwick to come in and bolster Howard, ensuring the CSA didn't get any of the highlands to the south and east of town.
On the 2nd day, the day Lee sent Longstreet to charge the roundtops, you have to look at just how good that terrain was. IF Longstreet had taken it, and the CSA could have mounted their Parrott guns up on top of those hills, the Union would have been in serious trouble. What's more, there's no reason to believe that if Longstreet hadn't delayed and stalled that he couldn't have actually taken it. He whined about about it for so long, his glum assessment became a self fulfilling prophecy.
On the 3rd day, Pickett's charge defies logic. It's almost as though Lee was possessed. It was very uncharacteristic for him, as he was painfully aware of the numeric advantages the Union possessed and just how dear each and every casualty was to the CSA.
On the Union side, there's a whole hatful of stupid things that they did. First, O.O. Howard, on the first day... Who orders their men to enter a densely wooded grove, then just stop? He's damn lucky he and his men survived that day and he very easily could have been wiped out. On the 2nd day, Sikes' adventures in the Peach Orchard border on criminal stupidity and disobediance. Meade had a fairly strong defensive line set up and Sikes decided to open a huge hole right at the lynch pin, because he wanted to impress some journalists he had along with him. He was damn lucky to have lost only his leg... McLaws and Lafyette had him surrounded on 3 sides and came this || close to pinching his entire corps off from the main union line. Not reinforcing the roundtops was incredibly stupid, and it's amazing that Chamberlain was able to hold.
On the 3rd day, the Union sat back and waited. Given their shortsighted offensive maneuvers up until then, this was probably their wisest move thus far in the war. The only thing I don't understand is why they didn't have a counter-strike prepared for Pickett's charge. They knew it was coming for close to an hour, and once the 1st corps turned the tide at the bloody angle, they should have sprung... The CSA would have been divided in half and possibly the entire ANV would have been destroyed. They had to settle for chasing the hospital trains the following day, slim pickings at best.
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