This is a very intriguing topic. With so many key points in history, just small changes two centuries ago could cause so many things to change in the future.
For instance, George Washington was named commander-in-chief, but his chief opponent for the job was John Hancock, president of the Second Continental Congress. What would happen if Hancock was CIC? Would Hancock have been able to hold the Colonial Army together at Valley Forge in 1777, not giving them the chance to defeat the British in 1781? Hancock's signature is famous. Would US currency look pretty interesting if the font size was really big?
In another interesting bit of history, George Washington first came to prominence by winning a seat in the Virginia House of Burgesses by offering large quantities of liquor near the polling stations, winning election by the tankard. If he had not done so, it's possible no one today would have ever heard of George Washington.
It was West Point, ironically, that Benedict Arnold was trying to sell out to the British. What would have happened if Major Andre had not been captured? Would West Point have fallen? Would the British have won the day? Would West Point, located in New York, have become the principal military academy in the United States?
After the victory, here's one of those interesting tidbits. German almost became the national language of the new United States, failing in the Continental Congress by one vote. Who would be on the currency if German was the national language?
Would the United States have been more sympathetic to the Central Powers in World War I, having more affinity with Germany than Great Britain perhaps? With a Central Powers victory in WWI, there would never have been the hyperinflation of Germany in the 1920's due to the horrendous Treaty of Versailles, which led to the rise of Adolf Hitler, a little-known Austrian painter.
Or perhaps, the US sided with Germany in WWII?
Someone mentioned that Robert E. Lee chose to remain loyal to his home state rather than go with his beliefs; indeed he abhorred slavery and the concept of secession. Had he accepted the command of the Union Armies offered to him by President Lincoln before the first battle of the war, likely the war would have been over by the Battle of Bull Run (would never have been a "Second" Battle of Bull Run).
Lee had a very bad heart condition. The length of the war and the four years of witnessing horrendous tragedies exacerbated his condition, killing him in 1870, a mere five years after the Civil War ended. With little stress due to a short war, it is conceivable Lee could have become president of the United States. If an incompetent like Grant could, certainly Lee could have.
And if Lee had won, nobody would have ever heard of the failed banker, Ulysses S. Grant.
And here's a twist. In revenge, the Union Armies took over Lee's home in Arlington and turned it into Arlington National Cemetery. If Lee was a national hero with a short war, Arlington National Cemetery would never have come into being.
The name, Alan Pinkerton, may be familiar to many. He founded what's known as the Pinkerton Detective Agency. He was also Union General George McClellan's chief spy during the Civil War. McClellan was known for being overly cautious, causing him to lose (or fail to win) a number of battles. It's not well known that it was the incompetent Pinkerton who fed him stories of overwhelming Confederate numbers when often the Sourthern troops were outnumbered 2- or 3-1. Without Pinkerton, would McClellan still have run against Abraham Lincoln in the 1864 elections? If McClellan had won the Civil War, crushing Joe Johnston's and Lee's army in the Battle of the Seven Days in 1862, would he have defeated Lincoln? Would Lincoln have lived?
Harry Turtledove published a series of novels, starting with "Guns of the South", which starts with the supposition that the South won the Civil War. Lee becomes president of the Confederacy and abolishes slavery.
Sorry if this ran long, but I love alternate histories.
