Tuesday, 22 November 2016

WIND IN MY HAIR A Kaleidoscope of Memories by Josephine Loewenstein

A Kaleidoscope of Memories
Josephine Loewenstein

‘Josephine Loewenstein has lived most of her life in the whirlwind wake of husband Rupert, amidst high society, the Rolling Stones, royalty and the fast lane of the 20th century. But here is a surprisingly dispassionate and acute observer of this passing show, by no means mesmerised or dazzled by it. There is a lot to read between the lines.’
In Wind In My Hair, Josephine Loewenstein captures the rich kaleidoscope of a life lived to the full. Many of the worlds she has been part of have vanished, or are fast disappearing. By breathing new life into them, she has created a collage of memories in which autobiography and a sharp ear share the page with cameos of the larger-than-life characters whose paths have crossed hers – many of them famous, others who cast a brief, but occasionally notorious, glow on their age, and are now shadowy footnotes.
Happily she maintains a sense of distance, even when she is at the heart of the story. Privilege and austerity punctuated her childhood. She spent much of the Second World War at Ledbury Park, her grandparents’ ancient half-timbered house in Herefordshire. Later she trained at the Sadler’s Wells Ballet School under the formidable Ninette de Valois, appearing in the opening performance at Covent Garden in 1946.
Forced to give up her career because of her height, Josephine escaped to Rome, a city bursting with colour and vitality in contrast to the shortages and gloom of post-war London. Marriage to Prince Rupert Loewenstein introduced her to a dolce vita lifestyle, in which she somehow successfully contrived to be both participant and observer.
Throughout, Princess Josephine casts an often funny, occasionally moving sideways look at this patchwork of parties, people and places. Yet for all the wealth and glamour, there is a poignancy about her observations, a sense of the transience behind the glitter and bravura, that makes Wind in My Hair refreshingly different to many other memoirs.
Sewn hardback with jacket, 185 x 244 mms
196 pages, illustrated throughout in colour and black and white

ISBN 978-0-9929151-7-9

Josephine Loewenstein Remembers the Heyday of High Society

Ahead of her memoir, socialite Josephine Loewenstein reminisces with old friend (and V.F. contributing editor) Reinaldo Herrera about their joyful antics in Rome and St. Moritz—before paparazzi and the Daily Mail were even a concern.

NOVEMBER 18, 2016 5:03 PM

Josephine Loewenstein— jet-setter, high-society fixture, and former wife of Rolling Stones manager Prince Rupert Loewenstein—has never been short of good personal anecdotes to tell at a party. So, one day, she decided to write them all down.

The result is Wind in My Hair: A Kaleidoscope of Memories, an autobiography that chronicles everything from her childhood in W.W. II era London, to her café society days in Rome, to her rock ’n’ roll life with Mick Jagger and Keith Richards.

Ahead of the book’s publication by Dovecote Press this week, the author reminisces with old friend and V.F. contributing editor Reinaldo Herrera about time gone by.

Vanity Fair: Josephine, it’s wonderful to be together. What gave you the idea for your book?

Josephine Loewenstein: Well, I started by writing short stories. Just jotting down interesting things, anecdotes, funny things the children said, and trips abroad.

Did you always have this interest in art?

Well, before the war, I went to the De Basil ballet school in Covent Garden.

That was the Ballets Russes de Monte Carlo?

That’s right. I always thought, “I have got to be a ballet dancer.” I had the audition with Ninette de Valois [at Sadler’s Wells ballet school] when I was 12 or 13. This was when the Opera House reopened in 1946. It had been a dance hall in the war.

When did your ballet career last until?

Til about ’49, ’50. I was very unhappy with my mother and my health went right down, so my father said he would buy a house in London in Montpelier Square and I could live with him. But one of my friends said, “I’m going to Rome, why don’t you travel with me?” Nine pounds for a one-way ticket on the train. Can you imagine?

That was the beginning of the Rome years. The dolce vita!

The dolce vita! What a wonderful mixture of vita and “grand” life! People who don’t know that generation cannot imagine Roman palaces, filled with footmen in full livery and white wigs and silk socks.

It was a very interesting mixture of times, because you had Americans who had come to Europe, and then you had Europeans that were living in America. You had film stars, and duchesses who didn’t know what a film star was.

And who would never consort with them in a social way, at all.

I think café society was brilliant and democratizing because it was the first time that everybody, from all strata of society, went out together. In 1958 or 1959 Mr. Badrutt [who was one of the owners of the Palace Hotel] told me, “This is the greatest year St. Moritz has had since before the Second World War.” It was an incredible mixture of the Agnellis, who were the kings of everything, and Princess Pallavicini, and Mr. Niarchos and that entire group . . .

And Sunny Auersperg . . .

Life in St. Moritz was special. There was no paparazzi; no press. You could do anything. I remember playing sardines in the dining room of the Palace Hotel. You’d get underneath tables of people you’d never met, and hide, and they were delighted! It was a very simple and free life because of the lack of newspapers.

Nobody bothered you, nor did you bother them. How it has changed.

And you didn’t know if so-and-so was rich or poor. Nowadays, they immediately introduce someone to you and they say, “He’s a billionaire” or “He’s a millionaire.”

That would have been thought very vulgar.

And in this fascinating time in your life, when did you meet Rupert, your husband?

Oh, much later on: ’55-ish. I think I met him at Oxford. We married in ’57. He met the Rolling Stones through Christopher Gibbs, who was friends with Mick Jagger

Mick had asked Christopher “Who can help us run the business, because we’re making a lot of money but we’re not seeing anything.” And Christopher said, “This is just the man you want: Rupert Loewenstein.” From then on, he ran the Stones for about 34 years.

They loved him and he loved them. To see Rupert Loewenstein and the Stones together is like seeing oil on one side and vinegar on the other. And yet they melded, and made the best salad dressing in the world.

Mind you, it was a very hard life for him, because the Stones lived only at night. He was up all night telephoning Los Angeles and the lawyers. Rupert was unbelievably patient. He had to be. Those were difficult times, when everyone did what they fancied, really. I won’t say more than that!

There are some interesting anecdotes about Keith Richards in the book.

He’s a very amusing person. Very kind, very charming, and brilliant. Mick and Keith are both good company. They’re interested in everything, whatever the subject!

Quite wild lives?

It was very wild. Less so now!

How late pop-hating Bavarian prince became 'Rupie the Groupie' and made penniless Rolling Stones billions in tax exile (while also keeping them out of jail for drugs)

Prince Rupert Loewenstein has just died aged 80
He was the man who kept the world’s most famous rock band from jail
The merchant banker could trace his family back to the 10th century
He turned the near-bankrupt British group into one of the most efficient money-making machines in the business

PUBLISHED: 00:34 GMT, 23 May 2014

His epitaph should read ‘It’s only rock ’n’ roll . . . but I loathe it’.
Yet it was this unlikely figure — a portly, pop-hating Bavarian nobleman — who saved the Rolling Stones from extinction.
Prince Rupert Loewenstein, who has just died aged 80, was the man who kept the world’s most famous rock band from jail and bankruptcy, using his expertise in tax-avoidance.

In full, it was His Serene Highness Prince Rupert zu Loewenstein-Wertheim-Freudenberg, Count of Loewenstein-Scharffeneck.
Keith Richards was more cautious.
‘He didn’t like rock and roll. He thought "composing" was something done with a pen and paper, like Mozart,’ said the Stones’ guitarist.
‘He’d never even heard of Mick Jagger when he met him.’
Yet the merchant banker, who could trace his family back to the 10th century, turned a near-bankrupt British group into one of the most efficient money-making machines the music industry has ever known.
The Rolling Stones are often labelled the ‘Billion Pound Band’, but that’s a massive understatement — since 1989 they’ve grossed twice that.
Their last tour pulled in £341 million. Mick Jagger is worth £200 million, Keith Richards almost as much.

No surprise, then, that their aristocratic eminence grise was once dubbed ‘the human calculator’.
But what drew an Oxford-educated, Savile Row-suited princeling into the orbit of the Rolling Stones?
The catalyst was Old Etonian Christopher Gibbs, a wayward art dealer ‘usually three feet off the ground on acid’, according to Richards, who’d adopted him as a mentor as they navigated their way through the drug-crazed Sixties.
Gibbs’s bohemian-toff credentials gave him access not only to the princes in town — including Rupert — but also to the paupers, as the Stones then were.

The band had parted company with their first manager, Andrew Loog Oldham, and fallen into the rapacious grip of the man who split the Beatles, Allen Klein.
Klein had leeched the Stones’ already depleted finances, and the relationship ended in tears and a set of lawsuits that were to last the next 18 years.
‘Chrissie’ Gibbs cornered Loewenstein, who part-owned a merchant bank, and told him his friends needed help.
It was in 1968 that Loewenstein first walked into Jagger’s house in Chelsea.
The Stones were already a global phenomenon but, Loewenstein recalled: ‘There was no furniture in the house.’
Jagger admitted that the band, though working its socks off, had no money.
Initially, Loewenstein had grave doubts. He wondered whether he wanted to deal with a group of people he considered ‘degenerate, long-haired and, worst of all, unprofitable layabouts’.
Loewenstein, a devout Catholic, had developed a very different set of life-values from the Stones in his 35 years. Sex? Not for Rupert. Drugs? No way. Rock ’n’ roll? He abhorred it.
He attended the Stones’ legendary Hyde Park concert in 1969 — no doubt pinching his princely nose at all those idlers and wastrels lounging about on the grass — later describing it as being ‘like a Nuremberg Rally’.
It took some time for him to come down from his moral high horse, but his banker’s instincts told him the Stones could, one day, earn billions.
What’s more, he came to find the band, particularly Jagger who also had a sharp business brain, intriguing.
Loewenstein realised that with a top UK tax rate of 98 per cent at the time, a mountain of debt and years of litigation ahead, he simply had to get the Stones out of the country.
‘I selected the South of France as a suitable location,’ he said.
The group duly relocated, though Keith Richards admits they feared the move would kill the band’s popularity.
But it was in France, while recording Exile On Main Street (Loewenstein claimed the title was a reference to the group’s tax-exile status), that the band really got its commercial act together.
It was the beginning of the huge tours which were to give the Stones their special place in rock history. Loewenstein sanctioned the expenditure of vast sums on sets, trucks, lawyers, backstage personnel, dancers and singers.

In return, he sought commercial sponsorship and the Stones became the first band to do product-endorsement — making multi-million-dollar deals with Jovan perfume, Budweiser beer, Volkswagen and the Chase Manhattan Bank.
In years to come, they would get £6million for allowing Microsoft tycoon Bill Gates to use a snatch of their song Start Me Up to promote his Windows software.
All thanks to Rupert.
He was scrupulously honest and insisted on doing things by the book, less because of the inherent moral virtue in playing by the rules than because he saw it as a way of ensuring that the business would still be running next year and the year after that.
He rejected the time-honoured rock ’n’ roll custom of accepting cash in brown paper bags when the band were on the road, pointing out that one accusation of tax fraud could keep the Stones out of America, their most lucrative market, for a very long time.
In 1978, when an accountant turned up with $50,000 (£30,000) in a paper bag during a tour, he was railing at the band for continuing to jeopardise their future by encouraging unorthodox practices.
‘He taught the Stones that there is no such thing as free money,’ I was told by one former band associate. ‘But it took a lot of teaching.’

Although the rather stuffy banker gradually grew more accustomed to the weird and wonderful world of the Stones, earning himself the nickname ‘Rupie the Groupie’ from Jerry Hall, he maintained a certain distance, viewing himself as, in his words, ‘a combination of bank manager, psychiatrist, and nanny’.
His Mr Fix It skills were often tested. For example, when recording Exile On Main Street at Richards’ French house Nellcôte, the band had consumed an abundance of drugs.
Soon, Richards and his partners in crime were in deep trouble with the French drugs squad.
Jail beckoned. ‘We could be locked up for months while investigations took place.
There was no habeas corpus [a writ requiring a person to be brought before a judge or court],’ recalled the guitarist grimly.
The persuasive Loewenstein was able to get Richards off the hook in return for the band temporarily leaving the country.
In 1977, when Richards was arrested for heroin possession in Toronto, it was Loewenstein who suggested to the court that he pay his debt to society by playing a number of charity gigs to raise awareness of the dangers of drug abuse, saving his client a jail term — again.
In his autobiography, Richards describes how, when it was discovered that a soon-to-be-released Stones song called Anybody Seen My Baby? bore more than a passing resemblance to the Canadian country artist k.d. lang’s huge hit Constant Craving, Loewenstein was hauled in to troubleshoot the problem.
‘The record was about to come out . . . I had to call up Rupert . . . we had to include k.d. lang in the writing credits,’ recalled Richards.
With one call, Loewenstein had saved the reputation of the Jagger-Richards writing brand, plus perhaps several million dollars in legal fees.
Of the prince’s contribution to the band’s bank balance, Richards has said: ‘He re-ordered the finances so we didn’t get cheated out of 80 per cent of the takings.
On a $50 ticket, up till then, we’d get $3. He set up sponsorship and clawed back merchandising deals. He cleaned out the scams and the fiddles. He made us viable.’
The secret of the prince’s success was that he treated the Stones as a multi-national firm, restructuring their management company into a pyramid based on four firms headquartered in the Netherlands.
Decisions on where to record, and where to tour, were made on the basis of tax benefits.

At one point, Loewenstein became caught between Jagger and Richards in a power struggle over the direction the Stones should take — Jagger assuming complete control over tours and marketing, Richards claiming that everyone else in the band should have a say.
For a very long time, the two old friends refused to speak. It took all of Loewenstein’s diplomatic skills to stop the band breaking up altogether.
All its surviving members agree that it was Loewenstein’s enduring legacy which put the Stones back together and on the road for the money-spinning 50th anniversary concert at the 02 arena in 2012, and at Glastonbury.
But by then, after 39 years with the Stones, he’d had enough. In 2007, he parted with the band — amicably, although Jagger was angered by the publication last year of his memoir A Prince Among Stones.
‘Call me old-fashioned,’ the singer was quoted as saying, ‘but I don’t think your ex-bank manager should be discussing your financial dealings and personal information in public.’
Just how ‘old-fashioned’ it is to have one’s tax affairs cunningly arranged by a financial wizard is another matter.

In fact, despite the apparent gulf in lifestyle, language and clothing, Loewenstein and the Stones had much in common. Back in the Sixties the Stones thought of themselves as outsiders and risk-takers — and so, in his own way, did Loewenstein.
Born in Majorca, he may have come from an ancient Bavarian family, but his branch of it had lost its influence.
There are many princes in Germany, and it’s just as easy to feel you are bottom of the pile when you have a title as when you’re a penniless schoolboy from run-down Dartford like young Michael Jagger.
In 1962, when the Stones were still dreaming of storming the pop charts, Loewenstein had his own dream — of storming the City.
He’d read mediaeval history at Oxford and, with two fellow former students, went out to find the cheapest merchant bank he could buy — a snip at £600,000.
To the pompous ancients who then peopled the world of merchant banking, Loewenstein, at 29, and his friends and business partners Jonathan Guinness and Richard Cox Johnson must have seemed, with their alternative approach to money-making, just as brash and rebellious as the Rolling Stones.
The three of them worked tirelessly in one room, setting up deals and taking risks — just as, across town, the Stones were sharing a house and trying to write hits.
Yet, Loewenstein’s home life was always deeply conservative. In 1957 he married Josephine Lowry-Corry, granddaughter of the banker Lord Biddulph, and they had three children.
Extraordinarily, given the opulent life that he led from his grand house in Richmond Park, both his sons chose a different way: one becoming a Roman Catholic priest; the other a monk. His daughter Dora married an Italian aristocrat.
It might be said Loewenstein changed for ever the way the popular music industry makes its millions. Certainly, he made a handful of scruffy musicians incredibly rich.

Prince Rupert zu Loewenstein - obituary
Prince Rupert zu Loewenstein was a Bavarian aristocrat and banker who disliked rock and roll but made The Rolling Stones very rich
5:41PM BST 21 May 2014

Prince Rupert zu Loewenstein, who has died aged 80, was the Bavarian aristocrat who for decades managed the financial affairs of The Rolling Stones.
Loewenstein was a key member of the Stones’ entourage for almost 40 years. The subfusc banker’s suits and high Roman Catholic connections which made him such an incongruous figure amid a backstage ambience of sex, drugs and rock and roll were in some ways deceptive: he had a lively sense of humour, and he observed his clients’ antics with a worldly twinkle in his eye. “He’s a bit of a showman, a bit extraordinary,” one City colleague said of him. “He always lived life at a very high rate.”

It was as managing director of Leopold Joseph & Co, a small London merchant bank, that he was first introduced to Mick Jagger by a mutual friend, the art dealer Christopher Gibbs, in 1968 — though Loewenstein claimed at the time never to have heard of the band. Jagger — no slouch in financial matters himself — was increasingly angry at the handling of the Stones’ affairs by Allen Klein, the aggressive New Jersey accountant who had been the group’s manager since 1965 and whose terms included a 50 per cent slice of their recording royalties. “Half the money I’ve made has been stolen,” Jagger later told an interviewer — and his first question to Loewenstein was whether the skills of Leopold Joseph could extricate them from their contract with Klein.

“I discussed taking on the group with my partners but they were very much against any involvement, saying it would be bad for the image of the firm,” the prince recalled. “It was very hard to win them over, but I finally prevailed.”
Loewenstein later wrote that he and Jagger “clicked on a personal level. I certainly felt that [he] was a sensible, honest person. And I was equally certain that I represented a chance for him to find a way out of a difficult situation. I was intrigued. So far as the Stones’ music was concerned, however, I was not in tune with them, far from it. Rock and pop music was not something in which I was interested ... After the first two or three business meetings with Mick, I realised there was something exceptional in his make-up, that his personality was able to convert his trade as itinerant performer into something far more intriguing.”

From then on, Loewenstein was a particularly close personal adviser to Jagger, who developed a liking for rubbing shoulders with high society. Shortly after they met, Jagger helped to plan a White Ball at the Loewensteins’ home in Holland Park, which kept neighbours awake until a quarter to six in the morning. When one rang the police to complain, she was told: “We can’t do anything about it, Princess Margaret’s there.”
Loewenstein realised that a great deal more money could be made for the band from touring: “After reviewing a few of the basic documents, I realised [the money] would have gone to Klein and therefore they would have depended on what he gave them, as opposed to what the record company or the publishing company did. They were completely in his hands. What had also become apparent to me was that the band would have to abandon their UK residence. If they did not do this, they could be paying between 83 and 98 per cent of their profits in British income tax and surtax. I selected the South of France as a suitable location for them.”
By 1972 Loewenstein had managed to reach a satisfactory contract with Allen Klein (although litigation continued for a further 18 years), allowing the Stones to record with a company of their choice. He then set himself to find a new recording contract for them to replace the existing one with Decca; during their European tour of 1970 he conducted what amounted to a trade fair on their behalf from a series of hotel bedrooms.
The prince’s services extended not only to managing their money, negotiating their contracts and accompanying them on tour: he once described himself as “a combination of bank manager, psychiatrist and nanny”, while the tabloids christened him “Rupie the Groupie”. In 1978 he was called upon to provide an affidavit to a Toronto court as to the extent of Keith Richards’s casual spending — $350,000 in the previous year — as evidence that the guitarist was wealthy enough not to commit crimes in order to feed his heroin habit.
It was the prince who was most influential in persuading Jagger to go on touring through the 1980s and ’90s, as relations among the group members cooled and the wear and tear of advancing age took its toll. The prince also stood as godfather to James, Jagger’s son by Jerry Hall, in 1985 (the actress Anjelica Huston was godmother).
When Jagger and Hall parted, Loewenstein masterminded the financial settlement that followed — and remarked in a rare interview that “when families split up you have to make it absolutely clear whose side you are on at once”. It was due in large part to his wisdom that Jagger’s fortune is today estimated at more than £200 million.

Rupert Louis Ferdinand Frederick Constantine Lofredo Leopold Herbert Maximilian Hubert John Henry zu Loewenstein-Wertheim-Freudenberg was born at Palma, Majorca, on August 24 1933.
His father, Prince Leopold, a native of Salzburg, traced descent through the royal house of Wittelsbach from the Elector Palatine Friedrich I (1425-76), whose son Ludwig — by a mistress, Clara Tott, whom the Elector married to legitimise the child — became Count of Loewenstein, near Heilbronn in what is now Baden-Wurtemberg, in 1488. Rupert’s mother was a daughter of the Count of Treuberg, and the family’s connections could be traced throughout the Almanack de Gotha. Non-noble forebears included the Frankfurt financier Mayer Amschel Rothschild, founder of the famous banking dynasty.
The young Rupert was brought to England in 1940 and sent to Beaumont, the Roman Catholic public school. Later he read History at Magdalen College, Oxford — where he emerged as one of the glitterati of his generation — and began his City career as a trainee with the stockbrokers Bache & Co. He and a group of friends swiftly decided that the best way to make serious money would be to own their own merchant bank.
Together with, among others, Jonathan Guinness (now Lord Moyne), the exotic French Baron Alexis de Redé, and Anthony Berry ( son of the Sunday Times proprietor Lord Kemsley and later a Conservative MP who was killed by the 1984 Brighton bomb), he arranged to buy Leopold Joseph & Co from its founding family for £600,000.
The bank had been set up in 1919 by a German-Jewish immigrant who first came to London as a reporter for the Frankfurter Zeitung; three Joseph brothers remained in the business, which had been operating on a very modest scale.
Under Loewenstein’s leadership, it rapidly made a new name for itself in lucrative corporate finance work and investment advice for very wealthy private clients. His success with the Rolling Stones’ account brought him a number of other showbusiness clients, including Pink Floyd and (before his conversion to Islam) Cat Stevens.
In 1981 the prince left Leopold Joseph to set up his own business, Rupert Loewenstein Ltd, based in St James’s. He took his best clients with him, and once explained why he enjoyed working for people who had only recently made their fortunes. New money, he said, was “much more interesting than old. People with old money are nearly always having to be adjusted downwards.”
Loewenstein’s own money, both old and new, enabled him to live in grand style in later years in a former grace-and-favour mansion, Petersham Lodge — not far from the Jagger ménage on Richmond Hill — which he bought in 1987 for around £2 million.
But in parallel with a life of money and parties, there was also a spiritual side to him. He petitioned for the preservation of the Tridentine Mass — writing to The Daily Telegraph in 1975 about its numinous beauty — and held high office in ancient Catholic orders of chivalry: he was Grand Inquisitor of the Constantinian Military Order of St George and president of the British association of the Sovereign Military Order of Malta.
Loewenstein’s association with The Rolling Stones ended amicably in 2007 — although his publication six years later of a memoir, A Prince Among Stones, was said to have upset Jagger.
In the book, the prince wrote of his relationship with the band: “All the time I worked with the Stones I never changed my habits, my clothes or my attitudes. I was never tempted by the rock ’n’ roll lifestyle. Although I enjoyed a good vintage wine, I was never a heavy drinker, nor a drug-taker. I always aimed to maintain a strict discipline backstage, for security reasons, and tried to see that the band and the entourage did not get drunk or disorderly.
“To many outsiders it must seem extraordinary that I was never a fan of the Stones’ music, or indeed of rock ’n’ roll in general. Yet I feel that precisely because I was not a fan, desperate to hang out in the studio and share in the secret alchemy of their creative processes (something I never did since I couldn’t take the noise levels), I was able to view the band and what they produced calmly, dispassionately, maybe even clinically – though never without affection.”

Prince Rupert married, in 1957 at the London Oratory, Josephine Lowry-Corry, a barrister’s daughter who had trained as a ballet dancer at Sadler’s Wells until she grew too tall, then retrained as an opera singer. The honeymoon included a visit to the Wagner festival at Bayreuth.
The Loewensteins had two sons, Princes Rudolf and Konrad, both of whom became priests, and a daughter, Princess Maria-Theodora (Dora), who married an Italian count, Manfredi della Gherardesca, and became a director of her father’s business.
Prince Rupert zu Loewenstein, born August 24 1933, died May 20 2014

Rupert Louis Ferdinand Frederick Constantine Lofredo Leopold Herbert Maximilian Hubert John Henry zu Löwenstein-Wertheim-Freudenberg, Count of Loewenstein-Scharffeneck(24 August 1933 – 20 May 2014) was a Spanish-born Bavarian aristocrat and the longtime financial manager of the rock band The Rolling Stones. His affectionate nickname was "Rupie the Groupie". Loewenstein was named to the International Best-Dressed Hall of Fame in 2001.

A scion of the royal houses of Wittelsbach and Löwenstein-Wertheim, Loewenstein was born in Palma, Majorca, Spain, the son of Prince Felicien Leopold Friedrich Ludwig Hubertus zu Loewenstein-Wertheim-Freudenberg (1903–1974) and his wife, Bianca Henrietta Maria Fischler, Countess von Treuberg (1913–1984). Both were of part-Jewish descent.Henry de Worms, 1st Baron Pirbright was his father's maternal grandfather. Following his parents' separation, he and his mother arrived in England in 1940. Loewenstein was educated at the Quaker St Christopher School in Letchworth, Hertfordshire, followed by Magdalen College, Oxford, where he studied medieval history.

After school, Loewenstein worked as a stockbroker for Bache & Co. In 1963, he was part of a consortium formed to buy the merchant bank Leopold Joseph & Sons, along with fellow Oxford graduates Jonathan Guinness, Richard Cox-Johnson and Louis Heyman.and he became a director of the resulting firm. Leopold Joseph had previously been family owned by the Josephs, and carried out only specialised lines of banking business.

Following the acquisition, the business was substantially expanded to include advice on issues and mergers, investment advice, and particularly currency trading. By 1971, the firm had become one of the principal dealers in London in investment dollars. That year, it undertook a capital raising with a target of a net £940,000 to enable further expansion. In 1981, Loewenstein left to start his own company, Rupert Loewenstein Ltd, where most of his clients were new money, who he described as "much more interesting than old money. People with old money are nearly always having to be adjusted downwards; those with new money are much more realistic."

The Rolling Stones
Loewenstein was the Rolling Stones' business adviser and financial manager from 1968 until 2007.
In 1968, then working in London as a merchant banker, he was introduced to Mick Jagger by a mutual friend, art dealer Christopher Gibbs. According to Keith Richards, Loewenstein had never heard of Jagger before then. Jagger was of the opinion that the Stones' then manager, Allen Klein, was not paying them everything they were due.

Loewenstein is credited with transforming the Stones into a "global brand and one of the world's richest bands", in particular by encouraging them to take into account potential tax advantages in any decisions about where to record, rehearse or perform. He managed their release from an existing contract, which paid them almost nothing, and persuaded them of the tax advantages of leaving England and moving to the south of France. He channelled their earnings through a series of companies in the Netherlands, and got them to rehearse in Canada, rather than the United States, to reduce their tax bill.Richards said, "[t]he tax rate [in the U.K.] in the early '70s on the highest earners was 83 percent, and that went up to 98 percent for investments... It was Rupert's advice that we become non-resident".Loewenstein also copyrighted the famous red tongue logo, and enlisted corporates sponsors such as General Electric for tours.

Richards described how, until they started to tour large venues in the 1980s, the Stones did not make serious money. The first important one was the 1981–82 tour which broke box office records. By then, Loewenstein had reorganised the band's finances so that they did not "get cheated out of eighty percent of the takings... On a fifty-dollar ticket, up till then, [the band got] three dollars. He set up sponsorship and clawed back merchandising deals. He cleaned out the scams and fiddles, or most of them. He made us viable." In a 2002 interview, Richards said of Loewenstein: "He is a great financial mind for the market. He plays that like I play guitar. He does things like a little oil well. And currency—you know, Swiss francs in the morning, switch to marks in the afternoon, move to the yen, and by the end of the day, how many dollars?"

Loewenstein never got involved in the music. He said he preferred classical music and never played a Stones recording by choice; if he had to listen to rock and roll, he preferred The Beatles. Richards confirmed: "Rupert didn't like rock and roll; he thought 'composing' was something done with a pen and paper, like Mozart."

Loewenstein's daughter, Princess Dora Loewenstein (Maria Theodora Marjorie Loewenstein), wrote several first-hand accounts of life with the Rolling Stones, whom she had known since she was a child.

Personal life and family
On 18 July 1957, Loewenstein married Josephine Clare Lowry-Corry (born 26 January 1931). She is the daughter of Montagu William Lowry-Corry (1907–1977), who was a grandson of Edward O'Brien, 14th Baron Inchiquin and Hon. Mary Constance Biddulph (1906–1991), who was a daughter of John Michael Gordon Biddulph, 2nd Baron Biddulph.

The couple had three children:

Rudolf Amadeus Joseph Karl Ludwig Emmanuel (born 17 November 1957) who became a Roman Catholic priest in the Dominican Order.
Konrad Friedrich Ferdinand Johannes Ottakar Sylvester (born 26 November 1958) who also became a Roman Catholic priest.He belongs to the Priestly Fraternity of St. Peter.
Maria Theodora Marjorie (born 11 July 1966) who has been married since 1998 to Conte Manfredi della Gherardesca. Her godfather was Alexis von Rosenberg, Baron de Redé (1922–2004).
They lived in Petersham Lodge in River Lane, Petersham, London, a former grace-and-favour mansion, purchased for about £2 million in 1987. It is an early-18th-century house, built for the Duchess of Queensberry, and Grade II listed by Historic England.

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