I'd say Jefferson Davis, without a doubt. He was outnumbered, fighting a defensive war on multiple fronts, with states who did not have to obey his orders to contribute to the fight. He was President over a loose confederation of states as opposed to a nation like Lincoln, and faced a crippling economic blockade. I think he did a pretty amazing job considering what he was up against. Lincoln's position was certainly no bed of roses, but I'd have to give the edge to Davis in the difficulty department.
I agree with the second answer -- I think it was Davis who had it harder.
First of all, his country barely deserved the name. It had no history as a country and had to try to devise a governmental system while, at the same time, fighting for its life. It was also hindered badly by its doctrine of states' rights. This meant that Davis's government would have a hard time getting states to contribute to the overall war effort.
Second, I disagree that most people in the North thought the South would win easily. One reason people went to watch First Bull Run was they thought it might be the only batttle of the war. People in Europe didn't think the South would win easily either, or France and Britain might have recognized the Confederacy. This was another issue for Davis -- he had to try to get his country acknowledged as a country and to get help from abroad.
To give the other side of it, I would argue that Davis had it tougher, partly because the South was not as unified as some would suggest. There were different factions within the southern states and Davis had to try to hold them together and direct the political efforts as well as the military ones. Add that to the incredible abundance of war-fighting resources that Lincoln and the northern states had at their fingertips and Davis was facing an uphill battle. It did appear to be going the way of the South at the outset of the war and certainly the North struggled at times to maintain the political will to fight, but Davis knew that if they didn't win quickly and force a peace agreement, all was lost.
This is a nice question. I think that both had their challenges. I would side with Lincoln having it tougher for a variety of reasons. At the outset of the war, there was greater and more widespread belief that the South was going to win the war. The early battles of the war helped to give credence to this. At the same time, the objectives of the North were not as clearly defined. Lincoln was not elected into office with an overwhelming mandate and had to hold together a fragmented nation in the Union states as well as counter the unified and cohesive South. I think that Lincoln's poise as President and leader were defined by the early difficulties in the conflict, situations in which a weaker leader would have shriveled. In this light, I see Lincoln as the President who had it tougher. Yet, as I said, I think an equally compelling case could be made for Davis having a tough go at it, as well.
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