Here is a post covering Timeline 191 in its own entry with a bit more detail. Elements of What Madness is This? by Napoleon53 have been folded in, namely the Charles Oswald character and backstory.
Timeline 191
Timeline 191, Also known as the Southern Victory series, began in 1931 with the release of a short story Collection. This particular story was written by Winston Churchill as"What is Lee had not won at Gettysburg?" which was a What If story set in a world where the Confederacy had won its independence. While originally Churchill planned to end the story with both the US and the CS being absorbed into Britain through an alliance, he decided to hold off and do research on the Civil War. It was from this that he learned of Special Order 191, which was lost and began to wonder if it hadn't been. From this idea, Churchill wrote up the first story "Southern Victory", which became a novel. Dwight D.Eisenhower provided realistic battle strategies in a private correspondence.
Southern Victory(1931)
The Story begins with the messenger about to leave but realizing he's dropped a cigarette carrying the details of Special order 191. he picks it up and rides off. Without knowledge of the battle, Robert E.Lee defeats John B.McClellan and occupies Philadelphia. Britain and France recognize the Confederacy and the US is forced to do the same. The Emancipation Proclamation is never implemented, sitting on Lincoln's desk in a first draft. In the 1865, election Lincoln loses. Meanwhile in the Confederacy, they expand by buying land from Mexico, and even purchase Cuba. A second war breaks out but the British and French refuse to aid the Confederacy unless they abandon slavery, which they do under their new President Robert E.Lee. A second war begins and the US is humiliated. Lincoln becomes an avid socialist as a result.
Jumping forward to the first World War, the conflict begins again. This time Theodore Roosevelt(whom Churchill met and was good friends with) leads the Union against the Confederacy(led by Woodrow Wilson). This time with Britain and France being occupied, the Union wins. it as this point the story ends.
Settling the Score(1955)
While
Southern Victory was a success, Churchill was occupied by his career in politics. However, after the Second World War, he decided to return to depict the Alternate World War II. Churchill began writing in 1955. Now fully aware of the Consequences of several earlier events he could reflect on them. For example in Russia, he made mention that the Communist Revolution failed and mentioned Lenin and Trostky. However, Churchill wanted to represent Stalin in the story and to this extent he created "Joe Steele" as Stalin who had been born in America. the adopted son of George Custer, who was a General in the first book and had been credited with weaponizing "Barrels" or Tanks in the Timeline 191 universe. George Custer's son Michael however preferred the name Joe Steele and upon realizing the truth of his origins, that he was adopted, he kills George Custer and has Theodore Roosevelt assassinated by Annie Oakley during the Victory Parade in New York(that ironically ended the last Book). Roosevelt shrugs off being shot but then begins to proclaim "It takes more than one bullet to kill a..." before he is shot, a reference to the actual assassination attempt on him. Joe Steele then helps to lead a Socialist revolution in the US, while assisting Socialist leader Eugene V.Debs. Finally in 1932, he is elected President after orchestrating the assassination of Franklin Delano Roosevelt by sitting his mansion on fire. Churchill at least wrote FDR crawling out of his wheelchair and moving towards Steele as he watched, as if trying to kill him with his last breath. Churchill would joke about coming up with sadistic ways to murder his friends.
Featherston and the Confederate armies as depicted in the book
There was a Stalin analogue, but Churchill realized he needed a Hitler. He decided he would come from the South. Thus Jake Featherston was born. Featherston was a minor character in the first book, just a Confederate Soldier, but he was turned into a failed artist and his history made to parallel Hitler's life. Though Hitler himself is shown to be just a Colonel in the story. Steele and Featherston's rivalry echoed that of Hitler and Stalin with a battle of Pittsburgh paralleling the battle of Stalingrad. Churchill also focused on the conflict in Europe. He depicted a parody of himself running Britain during the war. Germany ultimately wins the war in Europe as Einstein never fled Germany because there were no Nazis. The nukes are used on Paris and London and the war finished. In North America, Featherston survives a nuke of the Confederate Capitol but flees on foot, where he is found by several African American soldiers, who brutally shoot him down in revenge.
The Story ends with Churchill writing a story about what if it had gone differently. Joe Steele had recently died and his right hand and General Patton had taken over. Patton himself hated this part of the story because he couldn't think of any universe, real or not, where he was a dirty Commie. The book mentions that Japan had kept growing and implied a cold war between Japan and America.
Flag of the United Socialist States of America
Back in the USSA(1997)
Churchill died in 1965, however this was far from the end of what he had started. Writers Harry Turtledove and Kim Newman loved the universe Churchill had created and wrote a book continuing the story, Back in the USSA. Released in 1997, the book covered the rest of the Cold War post 1955 unto the present. The two introduced Charles Oswald, the alternate John K.Kennedy, and gave him a full backstory. Realizing that British people, including Irish individuals were prosecuted in Churchill's story due to the hatred the US has with Britain, Kennedy would likely have changed his name. As such in this new setting, Kennedy's family lived in a walled off ghetto. John F. Kennedy slipped out one day and played with a young bot until an officer spotted them and beat young John. This incident led JFK to change his name to Charles Oswald after he and his brother murdered their family. This allowed Oswald to rise in the ranks and eventually succeed Patton. Oswald became a new antagonist in the series after the big egos of Steele and Featherston, though he was far more charismatic during the Cold War. His storyline concluded with him threatening to start World War III by launching nukes until a rebellion led by Richard Nixon finally stopped him.
Other elements focused on includeThere was also a focus on Britain which became an analogue of OTL Japan as it recovered from World War II before becoming an analogue to America in this world. There's also Russia, which was similar to OTL Britain. Given the book consisted of several short stories, the details were more sparse, but interesting tidbits include Anne Frank serving a Martin Luther King Jr type role while Dr.King himself fulfills an Elie Weisel type role. Alfred Hitchcock releasing a Knights of the Round Table film similar to the Seven Samurai. The cold war ending with Emperor Hirohito's death, China becoming Communist as a parallel to China, and Kurt Vonnegut in a Gorbachev type role in the USSA.
Fan Works
The Timeline 191 series was a huge inspiration for Alternate History with Alternate History.com providing several timelines based on it such as "After the End." and a Redux by Napoleon53 that adds a lot of juicy details now considered canon. This includes George Washington Carver normalizing selling Cocaine to children, the Union carrying out genocide in Mexico and the rise of insane prophet Billy Graham. These later contributed to the release of the mod for the game Hearts of Iron IV(TTL's Kaiserreich with Timeline 191 thrown in).
HBO Adaptation
Following the conclusion of their time on
Game of Thrones, David Benioff and D.B.Weiss announced their production of an adaptation of "Timeline 191". The production included several black actors in the creation process and HBO ensured that the Confederacy would not be portrayed sympathetically but as the undisputed antagonists, despite this there was some controversy following the announcement. Season One covers The Great War. Season Two covers the intervening period between the World Wars. Season Three cover World War II with Sean Penn as Jake Featherston. Season Four shifted focus to Charles Oswald, played by James Marsden, and Season Five focused on wrapping up the Cold War. Marsden did something thought impossible and surpassed Sean Penn as Featherston. The Cover for Season Four is now iconic, depicting the visage of Charles Oswald(JFK) wearing sun glasses and smiling sadistically as atomic bombs reflect off his lenses with his face covered in blood and the headline: "What Madness is This?"
Adrian McLoughlin as Joe Steele
Sean Penn as Jake Featherston
James Marsden as Charles Oswald
Part of the Advertisement for Season Four of "Timeline 191".
