Tried to deal directly with Lenin, turning up at the Kremlin gates, demanding to see the Russian leader (infuriating Lockhart in so doing).

Decided the best way to cause the overthrow of the Russian government was to assassinate Lenin. Began to plot his assassination and bribed two of Lenin's bodyguards, who agreed to help him. He also began consolidating factions of anti-Bolsheviks to take part in the plot and compiled a list of Russian military leaders to take over after the fall of the Bolshevik government.

Before Reilly could act, Lenin was shot by a woman, Fanya "Dora" Kaplan. Lenin survived and after Kaplan was executed, the Bolsheviks began to search for a plot and tracked down the two guards Reilly had bribed. They cooperated and identified Reilly as well as Lockhart. Reilly eventually escaped on a Dutch freighter. Nonetheless, he was tried in absentia and was convicted of conspiracy against the Bolshevik government and against the life of Vladimir Lenin. He was sentenced to death.

Despite his failure, his flight and his death sentence, Reilly was convinced that he could still Lenin and overthrow the Bolshevik government, begging Smith-Cumming to send him back in. The SIS chief declined. Nonplussed, Reilly endeavored to carry out his own mission.

Formed an alliance with anti-Communist Boris Sakinov, the head of the counter-revolutionary Union for the Defense of the Fatherland and Freedom. Sakinov was able to gain a following of 30,000 anti-Bolshevik troops. Unfortunately anit-Bolshevik forces within Russia were soundly defeated before Sakinov could lead his troops into the country. Despite this, Sakinov was elated to find other pro-pro-Monarchist anti-Bolsheviks in Paris who agreed to fund his counter-revolution. The Monarchist Union of Central Russia (also known as the Trust) sent his to Russia to meet with underground Trust sympathizers.

In truth, the Trust a front group, created by the Bolsheviks under the guidance of Feliks Dzerzhinsky (OGPU). Months later, Reily was introduced to "Trust" members and led him also going to Russia to meet with the Trust's council leaders. Upon crossing the Finnish border, he was arrested on February 27, 1925 and taken to Lubyanka Prison where he was interrogated.

Was notified that the death sentence against him was to be carried out. Reilly, according to Soviet reports, tried to barter with Dzerzhinsky, promising to pass along British and American intelligence secrets in return for his life. It was to no avail.

Claimed to have impersonated the Chief of Staff to Rupert of Bavaria, thereby gaining access to planning conferences of the German high command, information of great importance that he passed back to London.

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