Jennie Jerome was born in the Cobble Hill section of Brooklyn in 1854, the second of four daughters (one died in childhood) of financier, sportsman, and speculator Leonard Jerome and his wife Clarissa (always called Clara), daughter of Ambrose Hall, a landowner. She was raised in Brooklyn, Paris, and New York City. She had two surviving sisters, Clarita (1851–1935) and Leonie (born 1859). Another sister, Camille (1855-1863) died when Jennie was nine. Leonard Jerome was rumoured to also be the father of the American opera singer Minnie Hauk.
There is some controversy regarding the time and place of her birth. A plaque at 426 Henry St. gives her year of birth as 1850, not 1854. However, on 9 January 1854, the Jeromes lived nearby at number 8 Amity Street (since renumbered as 197). It is believed that the Jeromes were temporarily staying at the Henry Street address, which was owned by Leonard's brother Addison, and that Jennie was born there during a snowstorm.
A noted beauty (an admirer, Lord d'Abernon, said that there was "more of the panther than of the woman in her look"), Jennie Jerome worked as a magazine editor in early life. Hall family lore insists that Jennie had Iroquois ancestry, through her maternal grandmother; however, there is no research or evidence to corroborate this.
Lady Randolph was a talented amateur pianist, having been tutored as a girl by Stephen Heller, a friend of Chopin. Heller believed that his young pupil was good enough to attain 'concert standard' with the necessary 'hard work', which, according to author Mary S Lovell, he was not confident she was capable of.
Jennie Jerome was married for the first time on 15 April 1874, aged 20, at the British Embassy in Paris, to Lord Randolph Churchill, the third son of John Winston Spencer-Churchill, 7th Duke of Marlborough and Lady Frances Anne Emily Vane. The couple had met at sailing regatta on the Isle of Wight in August 1873, having been introduced by the Prince of Wales, the future King Edward VII. Although they became engaged within three days of this initial meeting, the marriage was delayed for months while their parents argued over settlements. By this marriage, she was properly known as Lady Randolph Churchill and would have been addressed in conversation as Lady Randolph.
The Churchills had two sons: Winston (1874–1965), the future prime minister, was born less than eight months after the marriage. According to his biographer William Manchester, Winston was most likely conceived before the marriage, rather than born prematurely. A recent biography has stated that he was born two months prematurely after Lady Randolph "had a fall." When asked about the circumstances of his birth, Winston Churchill would reply, "Although present on the occasion, I have no clear recollection of the events leading up to it." Lady Randolph's sisters believed that the biological father of the second son, John (1880–1947) was Evelyn Boscawen, 7th Viscount Falmouth.
Lady Randolph is believed to have had numerous lovers during her marriage, including Karl Kinsky, the Prince of Wales (the future King Edward VII), and Herbert von Bismarck.
As was the custom of the day in her social class, Lady Randolph played a limited role in her sons' upbringing, relying largely upon nannies, especially Elizabeth Everest. Winston worshipped his mother, writing her numerous letters during his time at school and begging her to visit him, which, however, she rarely did. He wrote about her in My Early Life: 'She shone for me like the evening star. I loved her dearly – but at a distance'. After he became an adult, they became good friends and strong allies, to the point where Winston regarded her almost as a political mentor, more as a big sister than as a mother. She was well-respected and influential in the highest British social and political circles. She was said to be intelligent, witty, and quick to laughter. It was said that Queen Alexandra especially enjoyed her company, although Jennie had been involved in an affair with her husband, the king, which was well known to Alexandra. Through her family contacts and her extramarital romantic relationships, Jennie greatly helped Lord Randolph's early career, as well as that of her son Winston. In 1909 when American impresario Charles Frohman became sole manager of The Globe Theatre, the first production was His Borrowed Plumes, written by Lady Randolph Churchill. Although Mrs. Patrick Campbell produced and took the lead role in the play, it was a commercial failure. It was at this point that Mrs. Campbell began an affair with Lady Randolph's then husband, George Cornwallis-West.
Lord Randolph died in 1895, aged 45. Attending a party hosted by Daisy Warwick, Jennie was mixing in the highest London society circles, was much admired by the Prince of Wales . Her husband's death freed her to move effortlessly in spite of her impecuniosity. Introduced to a much younger man, he was instantly smitten, and they spent much time together that summer. Returning from service in the Second Boer War, George Cornwallis-West proposed, and they were married in London on 28 July 1900. George had two sisters one of whom , Constance (known as Shelagh) was the first wife of the 2nd Duke of Westminster ("Bendor") , the other Mary (known as Daisy) was married the immensely wealth Prince of Pless . A captain in the Scots Guards, he was the same age as her elder son, Winston. Their romantic wedding was held at St Paul's Church, Knightsbridge. Around this time, she became well known for chartering the hospital ship Maine to care for those wounded in the Second Boer War, for which she received the decoration of the Royal Red Cross (RRC) in the South Africa Honours list published on 26 June 1902. In 1908 she wrote her memoirs, The Reminiscences of Lady Randolph Churchill. George doted on Jennie, amorously nicknaming her "pussycat". However, they drifted apart. The Churchills were becoming a dedicated literary family, and George, who was a financial failure in the City, slowly fell out of love with his older wife, who already had a family. Short of money, she contemplated selling the family home in Hertfordshire to move into the Ritz Hotel in Piccadilly. George Cornwallis-West was in fragile health when he recuperated at the royal skiing resort of St Moritz. Jennie took to writing plays for the West End, in many of which the star was Mrs Patrick Campbell.
Jennie separated from her second husband in 1912, and they were divorced in April 1914, whereupon Cornwallis-West married the actress Mrs. Patrick Campbell. Jennie dropped the surname Cornwallis-West, and resumed, by deed poll, the name Lady Randolph Churchill. Her third marriage, on 1 June 1918, was to Montagu Phippen Porch (1877–1964), a member of the British Civil Service in Nigeria, who was three years Winston's junior. At the end of World War I, Porch resigned from the colonial service, and after Jennie's death, returned to West Africa where his business investments had proven successful.
In May 1921, while Montagu Porch was away in Africa, Jennie slipped while coming down a friend's staircase wearing new high-heeled shoes, breaking her ankle. Gangrene set in, and her left leg was amputated above the knee on 10 June. She died at her home in London on 29 June, following a haemorrhage of an artery in her thigh (resulting from the amputation). She was 67 years old.
She was buried in the Churchill family plot at St Martin's Church, Bladon, Oxfordshire, next to her first husband.
According to legend, Jennie Churchill was responsible for the invention of the Manhattan cocktail. She allegedly commissioned a bartender for a special drink to celebrate the election of Samuel J. Tilden to the New York governorship in 1874. While the drink is believed to have been invented by the Manhattan Club (an association of New York Democrats) on that occasion, Jennie could not have been involved, as she was in Europe at the time, about to give birth to her son Winston later that month.
Jennie Churchill was portrayed by Anne Bancroft in the film Young Winston (1972) and by Lee Remick in the British television series Jennie, Lady Randolph Churchill (1974). She was also portrayed by Margaret Ann Bain in dramatic re-enactments during the 2009 Channel 4 documentary Lady Randy: Churchill's Mother.