alternatehistory.com

This is my first take on the Alternate History scenarios so feel free to add and expand your ideas on a world where Winston Churchill is the Master of Alternate History.

1931 - Winston Churchill's essay entitled If Lee had not won the battle of Gettysburg is published on If It Had Happened Otherwise: Lapses Into Imaginary History. (Note that this actually happened in our reality)

1932 - Churchill failed to spoke about the dangers of Germany's rearmament after hearing the news about Germany having the right to military parity with France. With that, He decide to expand his 1931 essay into a novel known as Gettysburg Differed. (Note that this is the POD event as Churchill did spoke about the dangers in real life)

1934 - Gettysburg Differed is released to the public and archived success that leads him to resign his Political Career and continues writing stories involving alternate history. At that time, He's researching a history involving Adolf Hitler.

1936 - Leader In Session is released to the public documenting a alternate life of Adolf Hitler as an successful artist. The novel has caught the interest of actor Charlie Chaplin and decide to adapt the novel into a movie.

September 1, 1939 - Poland is invaded by Germany at that time. Winston Churchill went to the radio and said that he tried warn about them but if it wasn't for his writing career, the invasion would never happened.

May 1940 - Oswald Mosley succeeds as Prime Minister of London.

September 1940 to May 1941 - The Battle of London ends with Nazi Germany winning. Following that, Adolf Hitler traveled to London to greet the nation and have his first meeting Oswald Mosley at that time.

October 1941 - Adolf Hitler and Oswald Mosley traveled to Japan and meets Isoroku Yamamoto on their plans to invade the American Soils at that time. Days later, He sends his set of troops to Japan and with Yamamoto's permission, The troops became allied with Japanese soldiers.

December 7, 1941 - The Axis Attack of Pearl Harbor occurs as Japanese and Nazi Fighters invade Pearl Harbor at that time. Following that, President Wendell Willkie decided that the Americans will now be involved in the second world war.

February 1942 - The Battle of Los Angeles occurs. A week later, Winston Churchill decides to begin his trilogy epic known as The Great War Beyond which rewrites the then-current war with Aliens involved.

April 30, 1945 - Adolf Hitler and his wife Unity Mitford committed suicide at the time. Upon hearing it, Winston Churchill changed the ending to the second novel which involves Hitler faking his death and is actually a Mrokaggian conqueror.

August 6, 1945 - The atomic bombing of Tokyo successfully ended the second world war.

1946 - The Great War Beyond: The Land & The Sea is released to the public.

1947 - The Great War Beyond: Days Of The Valkyrie is released to the public.

1948 - The Great War Beyond: The Atomic Twilight is released to the public.

1950 - Republic Pictures begin its serial adaptation of The Great War Beyond: The Land & The Sea. Unlike the novel, The movie serial is taking on a science fiction hero approach similar to Flash Gordon and set the movie in a future rather than an alternate history. Winston Churchill distance himself from the adaptation and instead is writing a novel involving his imaginary life as a Prime Minister.

June 1953 - Winston Churchill suffered a stroke which halts his unfinished novel. Weeks after the stroke, He slowly begins finishing the novel while writing ideas for future project after the novel is completed.

September 5, 1953 - Winston Churchill makes a rare appearance in the 11th World Science Fiction Convention for the first Hugo Award. He won the award for The Great War Beyond trilogy and is claimed by the press as "The Master of Alternate History".

December 1956 - Not long after finishing the novel in draft form, Winston Churchill again suffered a stroke and died at the age of 82.

1959 - My So-Called Political Life is released to the public. Around that time, Winston's ideas for future projects is taken the use of several science-fiction writers including L. Ron Hubbard, Issac Asimov and Philip K. Dick and written their projects in the spirit of the great British Sci-Fi novelist.

1979 - Steven Spielberg and George Lucas co-direct 1941 which involves the comedic take on The Battle of Los Angeles that's inspired in parts by The Great War Beyond: The Land & The Sea. It is not financially successful but grew into cult hit through Betamax and Laserdisc sales in the following years.

1994 - Inspired by the works of Winston Churchill, Harry Turtledove decide to continue the spirit and decides to make Alternate History novels himself. He started it with The Second Great War series which is expanded from Churchill's The Great War Beyond trilogy.

2011 - Jonathan Liebesman faithfully adapted The Great War Beyond trilogy with The Great War Beyond: Los Angeles starring Christian Bale, Jordana Brewster and Seth Rogen. It is financially successful and leads to the booming of Alternate History movies at that time.

Note that since this is a alternate history, I speculate that L. Ron Hubbard is still a writer while Betamax and Laserdisc is the major medium there. :)
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