Grand Duke Sergei Mikhailovich of Russia (; 7 October 1869 – 18 July 1918) was the fifth son and sixth child of Grand Duke Michael Nikolaievich of Russia and a first cousin of Alexander III of Russia.

He was born and raised in the Caucasus, where his father was viceroy. In 1881 the family moved to Saint Petersburg. He became a close friend of the then Tsarevich Nicholas. They grew apart upon Nicholas II's marriage and accession to the throne. Grand Duke Sergei remained a bachelor living at his father's palace in the imperial capital. He had a long affair with the famous ballerina Mathilde Kschessinska, who had previously been the mistress of Nicholas II. She was also later involved with Grand Duke Andrei Vladimirovich. Sergei recognized Mathilde's son as his own and remained their protector until his death.

Following family tradition, Grand Duke Sergei pursued a military career. He served as General Inspector of the Artillery with the rank of Adjutant General. During World War I he was chief of the artillery department, a position he was forced to resign amid controversy. He was then appointed Field Inspector General of Artillery at Stavka. After the fall of the monarchy, he remained in the former Imperial capital keeping a low profile. With the ascension of the Bolsheviks to power, he was sent to internal Russian exile.

He was murdered by the Bolsheviks along with several other Romanov relatives and his personal secretary at Alapayevsk on 18 July 1918, one day after the murder of Tsar Nicholas II and his immediate family at Yekaterinburg.

Early life

Grand Duke Sergei was born on , at Borjomi,Chavchavadze, The Grand Dukes , p. 203 his father's estate from Tiflis.Katin-Yartsev & Shumkov, Costume Ball at the Winter Palace, p. 54Hall, Imperial Dancer, p. 47 He was the fifth son and sixth child of the seven children of Grand Duke Michael Nicolaievich of Russia and his wife Grand Duchess Olga Feodorovna, born Princess Cecile of Baden. Named Sergei after St. Sergius of Radonezh, Grand Duke Sergei Mikhailovich spent his early years in the Caucasus, until 1881 when his family moved to Saint Petersburg. Raised in strict and militaristic environment, he received little affection from his parents. His father, occupied in military and governmental endeavors, remained a distant figure. His demanding mother was a strict disciplinarian and cold towards her children.

Like his brothers, Sergei Mikhailovich was destined from birth to follow a military career. He was two weeks old when he was enrolled in a military unit that was named after him: the 153rd Infantry Vakusnkii Regiment of HIH Grand Duke Sergei Mikhailovich.Cockfield, White Crow, p. 20

A Russian Grand Duke

Sergei Mikhailovich loved the military life and served in a number of regiments. Like his father, he was drawn towards ordnance and artillery. After graduating from the Mikhailovsky Artillery School, he started his military service in the Life Guard of the Cavalry Artillery Brigade. In 1891, he became aide-de-camp to the Emperor and in 1899 was promoted to the rank of colonel. In 1904, he was made major general in the House Guards Artillery Brigade of the suite of the Tsar. He replaced his father in 1905 as Inspector General of Artillery, a post he held until 1915 when he was removed under controversy during World War I. In 1908, he became adjutant General. In 1914, he was promoted to the rank of General of Cavalry. From January 1916, he served as Field Inspector General of the Artillery until he resigned his military post at the fall of the monarchy.

Sergei Mikhailovich was tall, reaching six-foot three, and was the only among Grand Duke Michael Nicholaievich's children to inherit their father's blue eyes and blond hair. He became prematurely bald and was considered the least handsome of a very good-looking family. He had a keen sense of the ridiculous, but was pessimistic, as influenced by his tutor Colonel Helmerson. He had the habit of saying "tant pis!" (so much the worse!) to any bad news.Alexander, Once a Grand Duke, p. 150 Widely considered rude and moody, he was at the same time sincere, affectionate, loved simplicity and was easily accessible without class distinction.

Grand Duke Sergei Mikhailovich was, unlike his brothers, interested in mathematics and physics, which coincided with his fondness for artillery. His only artistic inclination was choral singing, and he formed an amateur chorus of more than sixty voices, including some professional singers. They were directed by Kasatchenko, the master of the Imperial Theater. For a decade, the group met at Sergei's palace every Monday evening from 8:00 pm to 10:30 pm before the Russo-Japanese War stopped it. Like his brothers George and Alexander, Sergei Mikhailovich was also fond of numismatics and gathered a large collection of coins. Like all the Grand Dukes, Sergei was immensely wealthy. Beside his Grand Ducal allowance of 200,000 roubles a year, he received the income from vast personal states, which include a hunting lodge from St Petersburg. At the death of his father in 1909, his wealth increased even further.

He remained a bachelor, living in the household of his father, and later with his eldest brother on the Neva: the new Michaelovsky Palace in St Petersburg. The halls and corridors were so vast that Sergei used a bicycle to visit his brothers Grand Dukes George and Nicholas Mikhailovich who lived in other wings of the large Palace.

Ménage à trois

In the early 1890s, Grand Duke Sergei Mikhailovich was particularly close to his brother Grand Duke Alexander Mikhailovich. Traveling together to India, they had to stop their trip in Bombay in 1891 upon the sudden death of their mother. Both brothers fell in love with Grand Duchess Xenia Alexandrovna, their first cousin, once removed.Alexander, Once a Grand Duke, p. 129 She chose his brother over Sergei and married Alexander in 1894. During the last year of Tsar Alexander III's reign, Sergei and his brothers Alexander and George Mikhailovich were constant companions of the future Tsar, Nicholas II. Their closeness ended with Nicholas' ascension to the throne and marriage.

When Nicholas II, then the Tsarevich, broke off with his mistress, the famous ballerina Mathilde Kschessinska, he asked Sergei to take care of her. From 1894, Grand Duke Sergei, who was then 25 years old, became Kschessinska's protector. He provided generously for his mistress. In 1895, the grand duke bought a dacha for her in Strelna. Kschessinska, who was ambitious, used her connections to the Romanovs to promote her career. Sergei, as president of the Imperial Theatres Society, took an active role in the ballet world to secure a prominent place for Kschessinska in the Imperial Ballet. Although Sergei was devoted to Mathilde, she was not in love with him and used him as a tool to fulfill her ambitions. He remained her devoted friend through to the end of his life. He never married and found in Mathilde's company the substitute of a family life.

In February 1900 Kschessinska met Grand Duke Andrei Vladimorovich, who was a son of Grand Duke Vladimir Alexandrovich, Sergei's first cousin. Mathilde fell in love with Andrei and soon they started a new relationship.Hall, Imperial Dancer, p. 73 Grand Duke Sergei tolerated their affair remaining a close and loyal friend to the famous ballerina, but the relationship between the two Grand Dukes was tense. They tried to avoid each other while sharing the same woman for almost two decades.

The ménage à trois became more complicated when on 18 June 1902, Mathilde gave birth to a son.Hall, Imperial Dancer, p. 84 Both Grand Dukes were at first convinced they were the child's father. After the Revolution, both Kschessinska and Grand Duke Andrei maintained that Andrei was the father,Hall, Imperial Dancer, p. 85 but it was Grand Duke Sergei who looked after Mathilde and her son while he was alive. The child, who became known within the family by his nickname Vova, received the name and patronymic of Vladimir Sergeivich, although no surname was made public until 1911. The birth certificate showed Sergei as the father, and he was devoted to the child.Hall, Imperial Dancer, p. 86 The question of Vladimir's paternity remains unresolved. However, most sources attribute the paternity to Grand Duke Andrei Vladimirovich, who the child resembled.

Grand Duke Sergei Mikhailovich also had a relationship with Countess Barbara Vorontzova-Daskova, née Orlova (1870, Paris -1915, Petrograd), the widow of Count Ivan Illarionovitch Vorontzov-Daskov (1866–1897). In 1908 she gave birth to a son, Alexander, in Switzerland.Hall, Imperial Dancer, p. 128 The father of Alexander seems to have been Grand Duke Sergei Mikhailovich. Alexander (1908, Switzerland – 1979, New York) was adopted by a friend of his mother, Sophia Vladimirovna Dehn, whose grandmother was a daughter of Tsar Nicholas I. He spent his childhood in Italy where his adopted father was on naval service. Alexander was a well-known artist and often showed his watercolors at American galleries. He married twice and died in the U.S. in 1979.

War and revolution

After visits to AustriaAlexander, Once a Grand Duke, p. 242 and Germany in 1913 Sergei Mikhailovich reported to the Government of the feverish work of military factories of the central European powers, but his warning about an imminent war was not heeded by the Russian ministers.Alexander, Once a Grand Duke, p. 253Chavchavadze The Grand Dukes , p. 204 In the summer of 1914 just before the outbreak of World War I, Grand Duke Sergei was traveling near Lake Baikal when he fell ill with rheumatic fever in Chita.Cockfield, White Crow, p. 21 At his return to Mikhailovskoe, during the first days of autumn, his illness, complicated with pleurisy took a severe form. He spent five months confined to bed before being pronounced fit enough to resume his duties.Hall, Imperial Dancer, p. 167 He was appointed inspector general of Artillery and was attached to the general headquarters, once making a trip to Arkhangelsk to check on the munitions sent there by the allies.

As chief of the artillery department Grand Duke Sergei came under fire of the president of the Duma, Mikhail Rodzianko. Corruption and negligence were rampant in the department and there was a scandal over contracts. Kschessinskaya was accused of getting preferential orders for firms in pursuit of economic gains. The grand duke was blamed for not uncovering a band of thieves and protecting the dealings of his mistress. A special commission launched an investigation on the matter and in January 1916, Grand Duke Sergei had to resign as head of the artillery department.Hall, Imperial Dancer, p. 175 He was then appointed Field Inspector General of Artillery at Stavka.

He was in a position to deal with Nicholas II every day, living in the same headquarters train with the Tsar. He was increasingly pessimistic about the outcome of the war for Russia but he could not assert any influence over Nicholas II who only trusted his wife Alexandra Feodorova who disliked Sergei Mikhailovich and had listed him among her enemies. The Tsarina following the rumors of corruption that had clouded Sergei's reputation had pressed her husband to make Sergei Mikhailovich resign from the artillery department. The scandal over the bribes did not die down in the last period of Imperial Russia and Grand Duke Sergei spent nearly all his time at Stavka. He became more cautious in an attempt to distance himself from Kshessinskaya, who had used him in her quest for financial profit. About the outcome of the war, Grand Duke Sergei had no hope.Alexander, Once a Grand Duke, p. 275