The lives of pioneers are very often turbulent and short – such is the price of breaking the boundaries and venturing into realms that nobody reached before. 

Aviation pioneers are often an exemplar case of that. Female aviation pioneers – doubly so. 

The life of Evgeniya Mikhailovna Shakhovskaya, in addition to being short and turbulent, was violent, lavish, and quite exciting indeed. She was one of the first aviatresses in the World, and arguably, the first one who managed to get accepted into the military. 

While her aviation career was rather brief, she was a part of a military unit two decades before Sabiha Gökçen, the much-celebrated Turkish aviatress and a holder of Guinness World Record in this field. While much of Evgeniya’s actual achievements are a subject of speculation, there is a chance she was also the first woman pilot to see combat.

So, what was her life like?

“I am doomed”

Shakhovskaya, born Andreeva, was from a family of wealthy merchants. She received the title of knyaginya – a princess or a duchess – from her husband Andrey Sergeevich Shakhovsky, marrying into the world of royalty and being expected to adopt an appropriate lifestyle.

But that lifestyle did not suit Evgeniya well. Mechanically inclined, she was known to be more interested in riding horses, shooting rifles, driving and repairing automobiles. In fact, her habit of spending more time in a garage than with her husband was rather scandalous at the time, possibly leading to a divorce. 

This event signified the start of the new life for the young princess. In 1910, she visited the first aviation week in Petersburg, observing flights of Nikolay Popov, one of the first Russian aviators. Shakhovskaya was impressed; attempts to be enlisted into a flight school followed but were unsuccessful, likely due to her scandalous background.

The failure did not extinguish her enthusiasm. She still received her flight lessons, but to become an accredited pilot had to migrate to Germany. There she became a pupil of another famous Russian pilot Vsevolod Abramovich and received a pilot's license in August 1911. 

For some time she worked as a flight instructor at the German branch of the Wright Company, managed by Abramovich, also becoming his mistress. It is difficult to determine if she was really the first woman pilot from Russia – some say so, others present convincing counter arguments – but she was quite definitely the first who attempted to become a military one. 

In September 1911, Italo-Turkish War started, becoming the first armed conflict where aircraft were used. Tales of reconnaissance flights and bombing runs of early airplanes stirred imaginations; Shakhovskaya volunteered.

“I am going to perform aerial reconnaissance, a bersagliere [sharpshooter – AeroTime News] armed with bombs will be sitting behind me. We will fly to survey enemy positions. It is a great feeling – to fly over the desert at the altitude of 500 meters, to hear the buzz of bullets shot by enemy riflemen hunting for our airplanes. Even dying in such circumstances – such a beautiful death. And I am going to die sooner or later anyway, I am doomed,” Evgeniya is quoted as saying in the contemporary press, which reported that she was going to depart to the frontlines shortly.

She did not depart though. Italy declined her offer to volunteer, as did Bulgaria a year later. Despite those failures, she was simply adored by newspapers, often appearing in them as a socialite-turned-daredevil, complete with photos of her sitting in a Wright airplane besides Abramovich. 

Their romance was short and did not end well. In April 1913, an airplane piloted by Shakhovskaya crashed; the pilot received minor injuries but Abramovich, who flew together, was fatally wounded. The crash shocked Evgeniya and she vowed never to fly again.

A month-long career

The decision did not last long either. As the First World War started in 1914, Shakhovskaya volunteered again, this time into Imperial Russian Air Service. Her offer was, once again, declined. 

At the time the woman was, reportedly, suffering from severe depression – a horrifying crash left some lasting psychological damage. Possessing some important connections in royal circles, Evgeniya turned to popular healer Grigori Rasputin, eventually becoming one of his most prominent “clients”. 

While the therapy prescribed by the famous mystic may have helped with depression, it also left Shakhovskaya with crippling opium addiction, the only thing that rivaled the addiction she had to airplanes.

She worked as a nurse for some time, never losing the hope that one of her volunteering applications would be successful. That finally happened in December 1914. Her request was approved by the Russian Emperor Nicholas II himself, assigning her to the aviation detachment of Kovno fortress (now – Kaunas, Lithuania). 

There are conflicting reports of what happened during her military career though. The only sure thing is that it was brief, lasting for less than a month – before the end of the year Shakhovskaya was already dismissed on unknown grounds, following rumors of some affairs with high-ranking officers. 

According to some claims, she performed at least several reconnaissance missions, was wounded, and received some kind of award for that. A picture of a woman in military uniform – with bandages on her head and medals on her chest – are often presented in this context, although that woman is, quite certainly, not Shakhovskaya (as both the uniform and insignia are of a cavalry officer). 

She is not listed as a recipient of any medals as well and records of her war-time achievements are absent. Yet even if rumors about her heroics are not true, it is likely she did perform at least some flights in her service. Additionally, even the mere fact of her being accepted into service, well-documented and not up for a dispute, makes her the first female military pilot in the World. 

From victim to executioner

The career-ending dismissal was followed by an accusation of espionage. The fact that Shakhovskaya spent quite a long time in Germany, now the mortal enemy of Russia, played the center role here; her less-than-stellar reputation contributed. Many later researchers claim that accusations were fabricated, and there is no way to prove or disprove them.

She was sentenced to be court martialed, only for the Emperor to intervene once again and change her sentence to life-long imprisonment in a monastery. According to most reports, she spent the next three years there, only to be freed by Russian revolutionaries on the grounds of being “a victim of Tsar’s regime”. 

While at the time of the Russian civil war the Red army featured at least several woman pilots, Shakhovskaya was not one of them. Going with the flow with the new way of things, she found her place at Cheka, the newly formed Soviet secret police, the forerunner of the NKVD and the KGB.

Many accounts describe her duties as executioner, although it is more likely she was an interrogator. Her ruthlessness was quite infamous though. Reportedly she sought revenge on those who put her into prison, and – completely succumbing to opiates addiction – often did not hold back the narcotics-filled fury. 

Numerous versions of her death exist, from her being involved in some criminal affairs and executed, to being killed in a drunken brawl. The second one is more likely, although it has a fair share of romanticized details too. Reportedly, she shot her close colleague before being killed; reportedly, her last words were “[Here is] a red bullet from my white princess hands”. 

It is quite certain Shakhovskaya died in Kyiv, in 1920, at the age of thirty-one. A royalty, an aviatress, a media personality, the first female military pilot in the World, possibly a spy, and finally – a Cheka member, she quite definitely had a life to remember.