At age 26, Elwes met and wished to marry 19-year-old shipping heiress Tessa Kennedy, daughter of Geoffrey Ferrar Kennedy and Daška Ivanović. Kennedy's parents, however, disapproved of the relationship and instituted wardship proceedings. On 27 November 1957, Geoffrey Kennedy obtained a restraining order against Elwes from Justice Sir Ronald Roxburgh, barring the couple from marrying. The High CourtTipstaff was not authorised, however, to apprehend Elwes anywhere outside England or Wales. After initially attempting to marry in Scotland while being pursued by the press, Elwes and Kennedy eloped to Havana, Cuba, where they married in a civil ceremony on 27 January 1958 as guests of infamous American mobster Meyer Lansky, who provided accommodation for them at his hotel, the Habana Riviera. When Fidel Castro's revolution threatened the stability of the country the newlyweds fled aboard a raft with two National Geographic explorers who were sailing to Miami. From there they flew to New York City where they took out a marriage licence on 31 March. On 1 April, the couple repeated the ceremony to ensure they were legally married in Manhattan's Supreme Court officiated by Justice Henry Clay Greenberg. On 15 July, the two set sail for England aboard the liner SS Liberté docking at Southampton. The following day, accompanied by his wife and an attorney, Elwes turned himself over to authorities and was transferred to Brixton Prison where he remained for two weeks while awaiting trial for contempt of court for defying the judge's order to return Miss Kennedy to her parents. At trial the judge accepted that Elwes did love his bride but commented that every parent knows that love was not "readily convertible into bread and butter" for the support of a wife. In his ruling he directed that Elwes be released from custody but also ordered that Kennedy remain a ward of court. Elwes and Kennedy were married until the union was dissolved in London in January 1969. Elwes never remarried. He and Kennedy had three children, film producerCassian Elwes, artist Damian Elwes, and actor Cary Elwes.
Career
In January 1960 Elwes became the assistant editor of Lilliput Magazine until its closure in July of that same year. From 1960–62, he was the Company Director of Dome Press where he began the newsweekly Topic Magazine as editorial director, along with William Rees-Davies and Maurice Macmillan. In 1963, together with Nicholas Luard, he published and subsequently became the director of Design Yearbook, which developed into the book-packaging firm November Books. The company's clients included Thames & Hudson, a publisher of books on art, architecture, design and visual culture. In 1964, he co-wrote a book with Luard, Refer to Drawer: Being a Penetrating Survey of a Shameful National Practice – Hustling, which included illustrations by cartoonist John Glashan. Elwes subsequently became a member of the National Union of Journalists. Following in his father's footsteps Elwes then became a portrait painter, painting many of London's Clermont Set. Around 1967 he moved to Andalucia, Spain, where, with the aid of architect Philip Jebb, he designed a Mediterranean-style apartment complex, completed in 1970. Clients included Luard and the actor Hugh Millais. Elwes became part owner of a hair salon, Figurehead, on Pont Street, Knightsbridge. One of Elwes' portraits was of John Bingham, 7th Earl of Lucan, who disappeared in November 1974 after the murder of his children's nanny.
Death
Elwes committed suicide at 1 Stewart's Grove Chelsea with an overdose of barbiturates in 1975, about a month after the death of his father, and about a month before the death of his mother. His body was found by his girlfriend Melissa Wyndham.