The answer is Yes and No with a heavy dose of hell no.

So basically without getting into too many details the south had

1. Home field advantage since the Union had to go into the southern states to quell the rebellion.

2. Time. The ultimate goal of any kind of war like this is to tire out the invader and all the south had to do is defend and inflict unacceptable causulties and cost on the Union till they gave up.

3. Good Officers. The leadership of the Confederate army was overall very good. Lee, Stonewall, Beauregard, and Hood where all competent. Of note is that Union generals where still very capable as well and sometimes the South's generals are overplayed.

Now notice what I did not mention.

The Union had:

1. Men. twice as many people in the north vs the south. 3 times if you exclude slaves.

2. Industry. The Union had 10 times the factories the South had and had 10 times the workers.

3. Infrastructure. The north had a massive leg up on trains and train tracks as well as a generally uniform track standard. The South lacked a uniform track standard and was way behind on track length.

4. The Union had a country while the CSA was a very weak collection of states. Frank Lawrence Owsley argues the the headstone of the CSA should read "Died of State Rights". In so much as Strong Governors of states refused to send troops to help neighboring states out as well as a weak taxation policy meant it could not fund the war.

5. International support. Slavery being what it is and Europe's distaste for it at the time, with some political back and forth the Union was able to keep countries from supporting the CSA. Not a single country recognized the CSA, though France and UK give it Belligerent status.

So how could the south win? Not very easily. The fact is that the South did not use Fabian Strategy which would have played to all 3 of their major strengths. Robert E. Lee attempted several INVASIONS of the north, instead of averting major conflict, he perused it. Finally it ended up with the battle of Gettysburg after which the south never recovered.

EDIT: Since this blew up I want to address a few points that fellow redditors such as 0l01o1ol0 have brought up as well as questions such about Fabian strategy.

1. Several people asked WHY if its so obvious, did not Lee and the rest not use Fabian strategy. The Issue is that with this type of question it requires arm chair Strategery. To us its seems obvious and right. At the time it was not so. Even to this day you can make arguments for Lee pushing through Maryland and capturing Baltimore and maybe Philadelphia with even a chance to sack Washington DC. The thing about Fabian strategy is that its extremely demoralizing and very unpopular with the Political class and the citizens. It does not get the war over with a big battle it instead forces a major force to run around the country side (lot of the time forgeing on the land) while tiring out the enemy. Heck Fabius (who the strategy was called for) was fired because he used the strategy by the Roman senate, only afterwards when another general led them to a direct confrontations at the infamous battle of Cannae where Rome got utterly destroyed did they finally realize that Fabius was right.

2. Several people asked me why I did not bring up the navy. The US navy was an important advantage but it must be stated that it was a mid war advantage not from the start and inherent. Unlike today or for the last 100 years ,The US navy (in size and number of ships) was always a make shift kind of thing until around 1880 when the US started actually building a standing navy. Till then the US would build a navy and scuttle/let rot/sell off after a war was done. The US navy was almost completely dissolved after the Revolutionary war and had to be rebuilt for the Barbary wars and war of 1812. At the start of the Civil war the Navy had under 50 ships active. But by the end it had the largest navy in the world at over 600 ships. And again by 1886 they where down to 38 ships that where all obsolete.

Other people have already commented on the difference in industry and population, but this isn't just hindsight. Contemporaries were aware of the differences as well. An excerpt from William Sherman's conversation with a professor at Louisiana Seminary:

"You mistake, too, the people of the North. They are a peaceable people, but an earnest people and will fight too, and they are not going to let this country be destroyed without a mighty effort to save it.

"Besides, where are your men and appliances of war to contend against them? The Northern people not only greatly outnumber the whites at the South, but they are a mechanical people with manufactures of every kind, while you are only agriculturists--a sparse population covering a large extent of territory, and in all history no nation of mere agriculturists ever made successful war against a nation of mechanics. ...

"The North can make a steam-engine, locomotive or railway car; hardly a yard of cloth or shoes can you make. You are rushing into war with one of the most powerful, ingeniously mechanical and determined people on earth--right at your doors. You are bound to fail. Only in your spirit and determination are you prepared for war. In all else you are totally unprepared..."

The quote is from Lloyd Lewis's "Sherman: The Fighting Prophet," but you can read the full remarks to the professor at least, here.

No, the south never really did have a chance as things were. The north simply had more men, more money, more industry and enough resolve to use it for long enough to break the south.

The south lacked international recognition and with it access to the credit markets of London and Amsterdam.

The navy remained faithful to the Union, and without it the South lacked the ability to break the Union blockade and thus access to the markets to procure gunpowder and weapons to make up for their lack of industrial capacity. Even though blockade runners were able to get through the blockade and deliver Austrian and British arms and South American nitrates (to make gunpowder) early war, the noose tightened more and more for every day.

What were the strengths of each side?

The South.

• A majority of the pre-war officers and West Point graduates sided with the South. Although the number of pre-war officers were pitiful (indeed most West Point graduates had civilian careers by the time hostilities were opened), especially for the large armies that would be raised, the South had more of those with a formal military education.

• The south had more men experienced on horseback and could raise a cavalry force (that was more of a mounted infantry and recoinnasance force than true cavalry) that was far more competent than its Northern counterpart. It was not until 1863 that Northern cavalry proved able to best its Southern counterpart.

• The South had a martial tradition and a stronger tradition of both partaking in and officering the state militias.

The North

• Access to international credit.

• Access to the international arms markets.

• Far stronger industry.

• Larger population. Especially if one discounts slaves.

• Bigger economy.

• Continued arrival of immigrants, who could be promised citizenship with service.

• The entire navy and most if not all of the merchant navy. Also control of the shipbuilding and naval fitting establishment of New England.

• International recognition and diplomatic support.

Both sides were militarilly bumbling amateurs. Helmuth von Moltke the elder, the Prussian Chief of Staff and the brain behind the Prussian military superiority of the late 19th century and the engineer behind the victories against Denmark 1864, Austria 1866 and France 1870-71 said of the American Civil War that it was 'two armed mobs chasing each other around the country, from which nothing could be learned'.

The pre-war military establishment was non-existant. Cavalry was at most mounted infantry and a recoinnasance force, incapable of charging enemy infantry formations, battlefield pursuit or operational information control (ie screen their own forces from enemy scouts and keeping a check on the enemy and his movements).

Staff experience was non-existant. A few officers had been with Scott during his Mexican march, arranging logistics and staff work for a force that never exceeded 9 000 men.

Supply services and quartermasters were completely unprepared for handling forces 50-100 000 men strong and resulted in extremely large, heavy and clumsy supply trains and an inability to operate large forces away from rail heads or naval supplies (the latter only for the North). Manouver warfare was almost completely impossible.

Training and conditioning of the troops was inadequate - both sides used Napoleonic tactics, were unable to charge home at critical times (such as Fredericksburg or Picket's charge).

Both sides proved unable to fight decisive battles - the victorious army was always incapable of battlefiedl pursuit, being as exhausted and disorganised as the defeated army. At the Battle of Königgrätz 1866, the Prussian cavalry took more than 9 000 prisoners by pursuing the retreating Austrians in less than an hour, before Austrian counter-charges forced them away and covered the Austrian retreat.

Both sides learned quickly and improved with experience, but generally, both sides were pretty bad.

As for turning points - the invasion of Kentucky, opening that front, the fall of Fort Donelson and Fort Henry, the loss of New Orleans (and opening of the Mississippi for Northern actions and supply), the defeat at Shiloh and the defeat at Gettysburg are probably the most important points I'd say nailed the faith of the Southern cause.

This is tricky, and really comes down to how you define "winning" the war. Pmaj82 covered it pretty well, but at the end of the day the two sides had very different war aims. Now, with the way the South actually fought the war, no, there was very little chance they could have won. But the war would have been completely different had they done things differently.

The South wanted independence, and the North wanted to maintain unification. The Confederacy did not need to sack Washington, burn Philadelphia, and occupy New York in order to win the war. They simply had to survive. The Union on the other hand absolutely needed to force the Confederacy to capitulate, or otherwise occupy a landmass the size of Western Europe.

The North had a huge advantage in industry, a massive naval advantage, and an overall population advantage. However, the South could have (and some generals wanted to) simply played a purely defensive war. The "Time for Land" strategy would have involved defending key strategic areas, and forcing a war of attrition wherein the Union would be forced to attack over and over again. Wherever the Confederacy lost, they would fall back and defend the next ridge/town/river. The Union would never be able to occupy the entirety of the South, and unless the Confederate army was well and truly smashed, would likely eventually be forced to cease hostilities due to outrage at home.

Had the South focused their entire forces on a few key areas and played a defensive war, things could have been very different. Instead, they made several invasions into the North, and stationed troops all over the South at the requests of local governors. Confederate troops who could have been defending the boarder instead spent years stationed in small towns in Georga, Arkansas, and Mississippi. Had the South played to their strengths instead of going on the offensive, we would be studying an entirely different conflict.

Ignoring a potential alternate history however, there were times when Union morale at home was dangerously low. Striking a low point in 1864, it is entirely possible that a major loss would have forced Lincoln to end the war due to public opinion. Alternatively, had Lee won a major victory while on Northern ground, the war could have ended right then and there. The war was not popular in the North, especially in the later years, and a major defeat on home ground might have been enough force an end to the conflict.

There's also the possibility of foreign intervention, and indeed the Confederacy certainly hoped to get Britain involved. The South produced 80% of the world's cotton at the onset of the war, and with Union blockades cutting off that supply, it was thought that European powers would become involved. Obviously this did not happen, but it seemed a very real possibility at the time.

Edit: Derp, sources. Most of this is taken from Edward Ayers' In the Presence of Mine Enemies, James McPherson's For Cause and Comrades, and McPherson and William Cooper's Writing the Civil War.

Most people here have good points. I personally believe that the South might have been able to end hostilities, at least for a time (whether the Confederacy would have been able to survive as a nation is another matter).

In Battle Cry of Freedom, James McPherson points to three "turning points" in the war: Antietam in the fall of 1862, Gettysburg/Vicksburg in mid-1863, and the capture of Atlanta in 1864.

Summarizing:

• In 1862, the Confederacy was desperately trying to secure international recognition, though there's some dispute as to how close the Confederacy actually was to getting it. It's worth noting that France actually favored intervention - they were trying to take over Mexico and wanted Southern support - but didn't want to antagonize Britain. There was some belief in the South that a major victory would bring support from Britain and by extension France. Antietam happened, and although it wasn't a decisive victory either way, it was enough (via Lincoln issuing the Emancipation Proclamation) to kill hopes for immediate intervention.

• By late June of 1863, Lee had pushed forward into Pennsylvania, the deepest Confederate advance of the war. Meanwhile, in the west, Vicksburg had resisted Union attacks for months. On July 4th, Vicksburg surrendered and Lee was forced to retreat. This was a huge blow on several levels: the capture of Vicksburg resulted (after the surrender of Port Hudson several days later) in complete Union control of the Mississippi River, and the defeat at Gettysburg was the Confederacy's last major offensive into Union territory. The dual defeats also resulted in a huge blow to morale.

• In the summer of 1864, there was quite a bit of war weariness in the North. Although Union armies were moving throughout the Confederacy, there was a perceived lack of progress, and Democratic politicians who favored peace (called Copperheads) exploited this belief. Even Lincoln himself was pessimistic of his chances for reelection, and did his best to ensure that the war would continue regardless of who was President. However, after a long summer of campaigning, Sherman's troops captured Atlanta on September 2. Atlanta had been one of the most important cities in the Confederacy (especially as a logistical center), and its loss was another huge blow.

Perhaps someone can clarify something for me. My father was a historian and told me one time when I was rather young about the civil war. He said that the reason the North won the war was because of the their rail roads. Granted, this is a very large simplification, because I was just a kid. There are obviously many reasons the North won, and no one sole reason. I believe my father's point was that in his opinion the largest reason that helped the North win the war was their railroads.

He went a little bit more in depth. He said the South had a large number of small, separately own railroads, that were often not connected, and were primarily built for cotton to be taken to ports. Because of this, they did not stretch North often, usually just heading east/west to ports. The North, on the other had, and long connected rails that moved North/South that were build for industry.

So how true is this? Did the rails play such a large role in the war? I know this is simplified, being for a kid, but is there some truth in this?