Historians believe that when the Academy of Fine Arts Vienna (1907-08) turned down the application of this struggling Austria-born artist, it forever changed the course of history.
"Unfitness for painting" was among the reasons cited in the Academy's rejection of young Adolf Hitler, back when he was living a bohemian life as a penniless artist in the Italian city.
It has since been concluded by many researchers that Hitler's anger at this rejection was among the seeds that would sew his infamous political career.
But, while historians analyse the factors which turned a mediocre artist into a monster, one thing's for certain: no-one in the early-1900s could possibly have imagined that Hitler's art would one day go to auction estimated at more than £150,000.
That's the value UK seller Mullocks Auctions believes Hitler's works could bring when they appear for sale in Ludlow Racecourse, Shropshire, UK, on September 30.
According to reports, the paintings were only recently discovered, found within a large estate in Austria's north after it was purchased by an unnamed lawyer.
Landscapes and buildings are the most common themes in the works for sale, with the future Führer's limitations as an artist clearly in evidence.
Other works include his study of an urn, 1909, and of a woman's
head, dated 1931
Take for instance, the above perspective errors in the above watercolour of a town house signed 'A Hitler 1910', in particular the windows.
Although the sale of Hitler's art remains illegal in some countries, including France and Austria, this isn't the first sale of his artworks to occur this year.
In April, a bizarre painting completed by Hitler in his later years (it features a burning Swastika in the background) was sold for £12,000.
Depicting a Hitler lookalike sat with Arminius (or Hermann), the German hero who defeated the might of the Roman Army in AD 9 and was described by Hitler as 'the founder of the Third Reich,' the painting was also sold by Mullocks.