[1] In spite of his family's pecuniary difficulties, Ryleyev was able to study at the Corps des Pages, an elite military academy attended only by members of the nobility, in Saint Petersburg.

[1] He gained recognition in literary circles in 1820, for penning a satirical ode To the Favorite, addressing an unpopular Tsarist official, Alexey Andreyevich Arakcheyev.

[5] One of those he assisted was twenty-year-old Alexander Nikitenko, an educated Ukrainian serf, working in Saint Petersburg, whom Ryleyev met in a bookstore.

[1] Ryleyev also edited and co-published a popular annual literary almanac, The Polar Star (Полярная звезда), with Alexander Alexandrovich Bestuzhev between 1823 and 1825.

[9] The three issues that Ryleyev published contained contributions from many of the foremost Russian authors and poets of the age, among them: Alexander Pushkin, Pyotr Vyazemsky, Vasily Zhukovsky, and Evgeny Baratynsky.

[11][12][5] Ryleyev could not support his family with his literary work alone, and after leaving the criminal court, he found employment with the Russian-American Company as a manager in the Saint Petersburg office.

[3][13] In 1823, Ryleyev was recruited by Ivan Pushchin to the revolutionary Northern Society, an organization of reform-minded individuals, mainly veterans of the Napoleonic Wars, dedicated to abolishing serfdom, and replacing the Tsar's government with either a democratic republic or a constitutional monarchy.

His verses were said to have inspired generations of revolutionaries and academics including Ukrainian exile Mykhailo Drahomanov, who wrote that in the 1850s-"The Confession of Nalyvaiko was copied in our secret notebook along with the works of Shevchenko and was read with equal zeal".

[20] Upon his return to the Russian Empire, his unit was stationed first in Lithuania and then near Ostrogozhsk (Ostrohozk), a city founded by Ukrainian cossacks, where he spent almost three years.

[20] Even after leaving the Russian Imperial Army at the end of 1818 and moving to St Petersburg he would regularly visit Ostrohozhk and the vicinity, to which he always referred to as 'Ukraine'.

In December 1825 he wrote to his friend Mykola Markevych: "I am a Russian, but I have spent three years in Ukraine: a short time for me, but sufficient to fall in love with that land and its fine inhabitants.

Ryleyev dedicated a poem written in the Summer of 1831 to an old acquaintance, Mikhail Bedraga who had nobly served in the Okhtyrka hussar regiment during the Napoleonic Wars.

[20] Ryleyev has been noted as being highly inspired by the Ostrogozhsk Cossacks whose descendants he became acquainted with and of having found them as “champions of liberty inherited from their heroic past”.

Ivan Mazepa famously led the Ukrainian Cossacks in revolt against Peter I and joined forces with King Charles XII of Sweden.

In 1823 he began crafting yet another poetic novel surrounding Ivan Mazepa, this time the protagonist was his ambitious nephew Andrii Voinarovsky, who joined his uncle's uprising but on his way to the Ottoman Empire was imprisoned by Russian agents in the SS Peter and Paul Fortress and died in Yakutsk after being in exile for 16 years.

Though the publication was said to have been inspired by Polish poet Julian Ursyn Niemcewicz and his work Historical Songs of 1816, Ryleyev was firm that Niemcwicz was not the primary source of his inspiration-"The duma is an ancient inheritance from our southern brethren.

The revolt was further hampered when its nominal leader, Prince Sergei Petrovich Trubetskoy, suffered a last-minute change of heart and chose to hide in the Austrian Embassy during the confrontation.

Nearby stood a vast crowd of civilian on-lookers, who began fraternizing with the rebels, but whom the leaders of the revolt did not call upon to participate in the action.

He sent Count Mikhail Miloradovich, a hero of the Napoleonic Wars, who enjoyed great popularity with both officers and ordinary soldiers, to parley with the rebels.

At the same time, a rebelling grenadier squad led by Lieutenant Nikolay Panov, entered the Winter Palace, but failed to seize it and retreated.