Obama seems to have an admiration for Lincoln, but I think there's another Civil War figure Obama resembles much more closely: George McClellan. The parallels are there: McClellan was handed an overwhelming advantage in force and materiel, and squandered it, fighting a series of defensive battles, while the smaller force of Lee seized the initiative and repeatedly dictated the terms of battle. There's even a regional thing at play, as the same regions are at political war against each other, North vs South, as were at real war with each other then. Like Obama now, McClellan's heart never seemed to be much in the war back then, which is one reason he wasn't a very good soldier. It all came to a head at Antietam, when McClellan could have ended the war two years and hundreds of thousands of casualties before it did end, but, well, he was McClellan, and the George McClellans of the world don't end wars, they just make brilliant maneuver after brilliant maneuver until their opponents decide it's time to fight. This time, there is no Lincoln around to give our McClellan the sack. We're stuck with him for the duration.
Some quotations about George McClellan:
If General McClellan does not want to use the army, I would like to borrow it for a time. -- Abraham Lincoln
In making his battle against great odds to save the Republic, General McClellan had committed barely 50,000 infantry and artillerymen to the contest. A third of his army did not fire a shot. Even at that, his men repeatedly drove the Army of Northern Virginia to the brink of disaster, feats of valor entirely lost on a commander thinking of little beyond staving off his own defeat. -- Steven Sears
The long inactivity of so large an army in the face of a defeated foe, and during the most favorable season for rapid movements and a vigorous campaign, was a matter of great disappointment and regret -- General Henry Halleck, Battle of Antietam after action report