Pippa Middleton's new boyfriend James Matthews with a tax avoiding hedge fund

'Incredible' Pippa's new beau: The millionaire with a tax avoiding hedge fund (and toxic playboy brother) who could be Kate's new in-law

Pippa's latest boyfriend is James Matthews, a 40-year-old hedge fund manager - and older brother of Made in Chelsea's Spencer Matthews

Spencer has admitted he always admired James' 'incredible' girlfriend

But who exactly is the older brother who has captured Pippa's heart?

Published: 18:21 EST, 22 January 2016 | Updated: 05:19 EST, 23 January 2016

Spencer Matthews, famed as a posh lothario on reality TV show Made In Chelsea, sheds light on his privileged childhood in his autobiography.

The son of a wealthy businessman, he spent his early years in a rambling Lincolnshire manor house where his three elder siblings, Nina, James and Michael, each exerted a formative influence upon him.

‘As a boy, I wanted Nina’s heart of gold, Mike’s general character, and James’s girlfriends,’ wrote Spencer. ‘Although both my brothers had good taste in women, James was always the pickiest of the two. He had some absolutely incredible girlfriends.’

Pippa Middleton and James Matthews (pictured together) were first rumoured to be dating back in October

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James is the older brother of Made in Chelsea lothario Spencer, who has previously admitted he was also jealous of his sibling's 'incredible' girlfriends

This little anecdote represents quite an accolade. Spencer, after all, is a voracious womaniser who owes much of his fame to his relentless pursuit of the opposite sex.

According to his autobiography, Confessions Of A Chelsea Boy, he has slept with no fewer than 1,000 women. And he’s just 27!

Yet when the book was published in 2014, older brother James’s role in inspiring this bed-hopping journey was overshadowed by other, more eye-catching, revelations.

It told, in somewhat tawdry detail, how Spencer had dabbled with cocaine and LSD, spent almost every night, for entire months, drinking in nightclubs, and enjoyed countless casual sexual liaisons.

One such encounter descended into a group sex session with six participants, including a man who attempted to perform a sex act on the author. Another involved him inadvertently sleeping with a South African prostitute.

In the context of such lurid episodes, Spencer’s small aside about his elder brother made little impact. Yet that could be about to change. For James just happens to have a new ‘incredible girlfriend’ on his arm — Britain’s most eligible young woman: Pippa Middleton.

Rumours of a relationship first emerged in the public domain in October, when James Matthews, a 40-year-old hedge fund manager, was spotted arriving at his Chelsea home with Ms Middleton, 32, late one evening.

The Duchess of Cambridge’s sister was photographed there again the next morning, clutching a bunch of red roses.

Since then, they’ve been seen on a string of dates, and spent eight days together over New Year in St Barths, an upmarket Caribbean holiday island where James’s parents, David and Jane, run a renowned hotel called Eden Rock.

Bachelor James has also been introduced to Pippa’s mother Carole: they were photographed together at a carol service in Chelsea, and then again outside an Indian restaurant earlier this month.

Pippa and the hedge fund manager have enjoyed several dates since - and they were spotted with mother Carole (pictured) following a carol concert in Chelsea in December

There were rumours that the couple had moved in together, but this has been widely dismissed

Although friends insist that a recent report claiming Pippa has moved into his five-bedroom home, which he bought for a staggering £17 million in 2014, is wide of the mark, the relationship appears to be burgeoning.

‘Pippa still has her own home where she lives, but things with James are now serious enough for her to also leave a toothbrush at his place,’ says one.

Neighbours report that Pippa’s Range Rover is spending ‘two or three nights per week’ outside the property, which boasts an underground cinema, a lift, a ‘staff room’ and a car-stacking garage in the basement.

While neither Pippa nor James has publicly confirmed their relationship, it has also been given the stamp of officialdom by Tatler magazine. The society journal recently published a guide to Mr Matthews, declaring he ‘looks a bit like Rupert Everett’ and is ‘happiest when in a blazer and suede loafers’.

It also mischievously suggested Ms Middleton has a thing for ‘tall men who work in finance’ since her previous two boyfriends, Nico Jackson and Alex Loudon, were similarly lofty City types.

But peer behind the Sloaney facade and James Spencer Matthews (to use his full name) is far more than just another posh banker.

For starters, despite the privileged upbringing, this handsome young man’s enormous personal fortune is almost entirely self-made.

‘James is a very bright guy who has worked incredibly hard from a very early age,’ is how another friend puts it.

‘He made a huge amount of cash from hedge funds, and quite a lot more in the London property market. I’m talking tens of millions. You don’t do that by 40 unless you’re a sharp cookie.’

Despite coming from a wealthy family, James is said to have made his fortune himself through hard work

Then there is the dashing figure that Matthews cuts outside the office.

As a schoolboy, he was one of Britain’s most promising young motor-racing drivers — achieving acclaim in the Nineties on the Formula Renault circuit.

More recently, he has competed in ultra-marathons and other exotic endurance races. Often, he takes part to raise money for a charity set up in memory of his brother, Michael, who died in 1999, shortly after becoming the youngest-ever Briton to scale Mount Everest.

Perhaps more intriguing still is the colourful nature of the extended family from which Matthew hails — which has a number of uncanny similarities to that of his new girlfriend. Like Pippa, he is the grandchild of a coalminer from the north of England.

Like Pippa, he boasts a parent of humble origin who has achieved great wealth: Carole Middleton is a former air hostess who grew up in a council flat, while James’s father David made millions in the car trade after starting out as a trainee mechanic in Rotherham.

To a degree, each family’s rags-to-riches journey to the heights of society speaks volumes for the social fluidity of modern Britain and the upwardly mobile nature of our moneyed new establishment.

Yet such fluidity is not always without cost. For while both families hobnob with either royalty or international celebrities (who stay at the Matthews’ Eden Rock hotel), they also feature black sheep.

Pippa, to this end, is occasionally embarrassed by her colourful uncle, Gary, who was once caught up in a tabloid sting in which he was alleged to have offered a reporter drugs and prostitutes.

Fiercely private James must suffer the excesses of his brother Spencer, who was photographed snorting cocaine in 2012 and was recently banned from ITV’s I’m A Celebrity after telling TV bosses he was taking steroids.

Every family has a black sheep, and Spencer, pictured with James Middleton, was photographed snorting cocaine in 2012 and was recently banned from ITV’s I’m A Celebrity after admitting he was taking steroids

He may also feel nervous at the prospect of any future glare of publicity shining on his business activities — since he works in an industry where attitudes to tax compliance are the subject of ongoing public controversy.

James cut his teeth in finance in the mid-Nineties, after leaving Uppingham, the £34,000-a-year Rutland public school, eschewing university to train as a trader at Spear Leeds & Kellog, a City firm now owned by Goldman Sachs.

At the time, he also had a growing reputation in motor racing, having displayed talent as a go-kart driver during childhood (the family home boasted a track) and later turning semi-professional.

In 1994, aged 18, he won the British and European Formula Renault championship for Manor Motorsport, beating Formula 1 legend Alain Prost’s record of ten consecutive wins, and winning 17 out of 22 championship races that year.

There was talk of Matthews heading to the Formula 1 circuit, but it wasn’t to be. Instead, he decided the world of finance offered a greater chance of enduring success.

Spencer was the youngest of four children

‘James was a fantastic driver and very, very talented,’ Manor Motorsport founder John Booth told me. ‘But he looked at the probability of making it as a Formula 1 driver, and took a pragmatic decision to go into the City.’

It turned out to be an inspired choice. In 1997 Matthews moved to a finance house called Nordic Options and rose quickly to become the firm’s senior equity options trader.

Aged 24, he left to launch his own firm, Eden Rock Capital Management, named after his parents’ hotel.

Based in Mayfair, it quickly achieved success as a fund which invested in other hedge funds.

By 2004, the firm looked after £131 million-worth of investments, according to trade paper HedgeWeek. In 2007, The Times reported the figure had risen to £1.1 billion.

However, quite where this investment money comes from, or how Eden Rock operates, is almost impossible to unpick. The firm has an office in Bermuda and runs a network of overseas subsidiaries, many of them in secretive tax havens. One subsidiary, Solid Rock Management, is registered in the British Virgin Islands. Another source of its revenues is a firm it provides ‘management services’ to in the Cayman Islands.

According to Companies House, an Eden Rock subsidiary has a bank account in the Caymans.

This complex corporate structure renders the company’s operations relatively opaque — and enormously tax-efficient.

Indeed, the most recent accounts for Eden Rock Capital Management LLP, its largest British company, show that it made £1,581,257 in profits, but paid just £3,143 in tax, an effective rate of 0.19 per cent, in the year to December 2014. The previous 12 months saw profits of £1,539,259 against tax of £11,684, an effective rate of 0.75 per cent.

There is, of course, nothing illegal about these financial gymnastics. But they certainly prove lucrative.

Indeed, in the early 2000s, James bought a house opposite the U.S. Embassy in Mayfair, before selling it a few years later and moving to a huge Notting Hill mansion whose previous owners include Nick Jones, the Soho House founder, and Desert Island Discs host Kirsty Young.

James may also be nervous about too much attention being cast on his business activities, since he works in an industry where attitudes to tax compliance are the subject of ongoing public controversy

In May 2014, he went up the housing ladder again, paying £17 million for his current abode: a vast semi-detached property in one of Chelsea’s smartest streets.

He is applying to build a first-floor extension that will allow a ‘vanity basin’ complete with ‘his and hers sinks’ to be added to the bathroom, along with male and female dressing rooms off the master bedroom.

While Pippa might be delighted at the prospect of such domesticity, four neighbours have complained. Yet if the life of James Matthews sounds glamorous, it’s nothing compared to that of his father David Matthews, a sun-tanned 72-year-old known by the nickname ‘The Band’ after an American rock group namesake.

Raised in a village near Rotherham, by a former coal miner who had taken over the local garage, he first worked as an apprentice mechanic for his father, before taking up motor racing in his early 20s.

In 1966, having built up a reputation on the Northern racing circuit, David married a pioneering female racing driver called Anita Taylor, who was known in gossip columns as ‘the most beautiful driver in the business’.

A daughter, Nina, was born the following year, but in 1969 the marriage broke up.

David continued to race until 1973, when he was forced into retirement after suffering serious injuries when he crashed at 130mph at Silverstone.

He then devoted himself to business, and slowly turned his used-car enterprise into Kirkby Central Group, which later became one of the region’s biggest dealerships.

David also remarried, to a Rhodesian-born artist called Jane Parker, the mother of his three sons — who remains his wife.

By 1985, the Matthews family enjoyed a ‘glossy lifestyle’, according to an interview David gave to the Daily Mail.

James paid £17million for his current semi-detached property in one of Chelsea’s smartest streets

It noted: ‘There’s a Jacuzzi in the bathroom, a jukebox in the kitchen, a full-size snooker table in the converted garage, a self-contained flat adjoining their luxury split-level home, and a spectacular view of a private lake from every picture window of their South Yorkshire village home.’

Two years later, just before Spencer’s birth, Kirkby Central was the subject of a £8.5 million takeover by Plaxton’s, a firm which made buses and coaches.

David was left in charge of the new firm, moving his family to Caunton Manor, an 18th-century country home near Grantham with 30 acres of grounds, historic glass houses, a trout pond and an indoor swimming pool which, at the flick of a switch, converted into a dance floor.

He reinvigorated Plaxton’s fortunes and, in 1989, engineered a second merger, this time with major car retailer Henlys, leaving himself in charge of one of the UK stockmarket’s 500 biggest companies.

David finally left when it began to suffer in the recession of the early Nineties. In 1995, after going to St Barths on holiday, he bought the Eden Rock.

Previously a favourite stomping ground of Hollywood stars, the hotel, on a cliff between two white coral beaches, had become somewhat run down.

Tatler mischievously suggested Pippa has a thing for ‘tall men who work in finance’ since her previous two boyfriends, Nico Jackson and Alex Loudon, were similarly lofty City types

Fancying a new challenge, at the age of 52, David moved in with his wife and eight-year-old Spencer (the other children were already pursuing careers in Europe) and devoted his energy and money to restoring it to its former splendour.

However, days after they arrived, the hotel was severely damaged by a hurricane. They took two years to rebuild it, turning it into an extremely glamorous location.

‘When there is nothing much to do in the afternoon he sets sail in his motor launch and goes fishing for tuna, with a decent bottle of Chardonnay in the cool box,’ is how an interviewer described David’s existence in St Barths after the hotel reopened.

Today, Eden Rock is one of the most exclusive hotels in the world, where everyone from Beyonce to Elton John, Brad Pitt and Leonardo DiCaprio has stayed. Its priciest suite costs £25,000 a night.

Would that be the honeymoon suite if James and Pippa were to advance their relationship enough to marry? Time will no doubt tell, but if they did tie the knot, this golden couple could even marry at the Eden Rock. It would be a fitting location, surely, for Pippa’s sister Kate, our future Queen, to add the wealthy, if at times potentially controversial Matthews boys, to her merry band of brothers-in-law.