He dropped out of college and was known as 'Barman Jack'. Yes this royal, who turns 38 today, has built a reputation as charming, reliable and faultlessly discreet...

There is one member of the Royal Family who has left Britain to live abroad, rubs shoulders with some of the biggest names in show business, makes his own living with no input from the Crown - and still stays on impeccably good terms with senior members of 'The Firm’.

He’s even on friendly terms with Meghan Markle and Prince Harry, whose score-settling memoir Spare caused so much upset in the corridors of Buckingham Palace.

But unlike the Duke and Duchess of Sussex, Jack Brooksbank - who celebrates his 38th birthday today (3 May) - has earned a reputation for being charming, reliable and faultlessly discreet

Since he married Princess Eugenie at St George's Chapel, Windsor Castle, in October 2018, he has proved to be both a dutiful participant at Royal occasions and a rock of support for his wife during some difficult times - including the death of Eugenie’s grandparents the Queen and Prince Philip, her mother the Duchess of York’s battle with cancer and the dark days when the furore surrounding Prince Andrew threatened to overshadow his two daughters.

Meanwhile, he has quietly gone about the business of building his career, moving his young family, including Eugenie and their two young sons August, three and Ernest, eleven months, to Portugal, where he now works as a marketing executive for the exclusive Costa Terra Golf and Ocean Club, an hour’s drive south of Lisbon.

The exclusive resort is the brainchild of the American property tycoon Michael Meldman, who created the £45-a-bottle Casamigos tequila brand with his film star friend George Clooney before selling the company to the drinks giant Diageo in a billion-dollar deal.

Jack was employed by the pair and their businessman partner Rande Gerber as Casamigo’s European brand ambassador and even served the spirit at his wedding reception.

It is clear that Meldman thought so highly of him that he took him to run the marketing side of his new Portuguese project, which is still in its infancy. The Royal in-law also runs a successful wine importing company based in London.

Jack, a longtime friend of Prince Harry who was one of the few members of the Royal family to escape criticism in ‘Spare, first met Eugenie at the Verbier ski resort in Switzerland in 2010, where the Princess was holidaying with her parents and older sister Princess Beatrice.

In 2018, Princess Eugenie revealed in a BBC interview that 'sparks flew’ from the beginning. 

The pair began dating and their relationship survived a long-distance separation three years later when Eugenie took a job with online auction house Paddle8, based in New York.

On the face of it, Jack - a commoner who had spent much of his time since leaving school working behind a bar - was not such a great match for a young woman who was born sixth in line to the throne.

Indeed, at the time of their meeting, Jack was working as a barman and 'meeter and greeter’ at the London bar and restaurant Devonshire Terrace, but there was always more to him than meets the eye.

The son of Old Etonian chartered accountant George Brooksbank and an heir to the Brooksbank baronetcy, Jack was educated at the £15,567-a-term Stowe public school and the University of Bristol, though he dropped out before taking his degree.

His mother Nicola is the great-granddaughter of First World War general and Conservative MP Sir Arthur Holland and Sir Frederick Charlton Meyrick, 2nd Baronet, another senior army officer and Torry MP.

Jack is even distantly related to Eugenie herself through his paternal great-great grandfather Thomas Coke, 2nd Earl of Leicester, who lived at Holkham Hall in Norfolk and who is also an ancestor of Sarah Ferguson.

After it became clear that he wasn’t cut out for university life, Jack gained his parents blessing before quitting to fulfil his ambition of working in the hospitality industry - he has said his dream is to own a chain of pubs.

He took a job at Chelsea's Admiral Codrington, a gastropub just a short walk from Sloane Square in the heart of Made In Chelsea country from where he was headhunted by businessman Piers Adam, who hired him to work around the corner at The Markham Inn.

In his three years at the Markham, Jack got to know Prince Harry and his friend Guy Pelly and began to move in royal circles - where he was known as ‘Barman Jack”. He then became general manager of Piers Adam’s Mahiki club in Mayfair, one of the capital's most exclusive nightclubs and an early favourite of Prince Harry and the young royals.

Jack and Eugenie were often spotted out together throughout the 2010s, sometimes accompanied by Prince Harry - who still enjoys a close relationship with his cousin.

In September 2016, rumours of a Royal engagement began to swirl after Jack, who had then been dating Eugenie for six years, was invited to spend time with the royal family and the late Queen Elizabeth II at Balmoral.

The same year, Jack and Eugenie were two of the first people Harry introduced to Meghan Markle - the Prince wrote in his book that the four met at a dinner party where they drank tequila and where he saw 'Euge hugging Meg, as if they were sisters.'

Speaking of Meghan meeting the first members of his family, he said she 'loved' Jack and Eugenie.

In the docuseries, titled Harry and Meghan, the couple recounted how Eugenie and Jack came to visit Meghan and Harry in Toronto in October 2016 before Harry’s relationship was made public. 

They two couples attended an apocalypse-themed party together at the city's branch of Soho House.

Harry also said that Meghan and he were 'deliriously happy' for Princess Eugenie when she got engaged to Jack, adding: 'since Jack was one of our favorite people.'

Jack finally popped the question on a holiday to Nicaragua, with their engagement being officially announced on 22 January 2018.

The official Royal Family Twitter account said at the time: 'The Duke Speaking the engagement in a video for the Royal Family's YouTube page, Jack recounted how he popped the question in front of 'a beautiful volcano, [while] sun was setting, birds were flying.'

Eugenie added: 'The lake was so beautiful. The light was just a special light I had never seen. I actually said this is an incredible moment, and then he popped the question, which was really surprising even though we have been together seven years. I was over the moon.'

The couple were married at St Georges Chapel in front of 850 guests. The bridal party included Princess Charlotte as bridesmaid and Prince George as page boy, with Princess Beatrice as maid of honour.

After exchanging their vows the couple beamed as they walked out of the church and kissed in front of 1,200 well-wishers before their short carriage ride through Windsor and back to the castle for their reception.

According to reports at the time, Jack's wedding speech was ‘filled with devotion to Eugenie’ and he told his new wife she 'lights up his life and makes him feel complete'.

Since becoming parents, Eugenie and Jack have enjoyed life away from the spotlight. In fact the only fleeting hint of scandal came a few months after August’s birth when he was photographed partying on a yacht with glamorous bikini-clad models while Eugenie stayed at home with their newborn child.

Rushing to his defence, his mother-in-law Sarah Ferguson insisted the event was part of Jack’s work as a Casamiga brand ambassador.

'Jack, who was on the front page, is a man of such integrity,' she said. 'He's just one of my most favourite people, I call him James Bond actually.

'He's just a superhero in my book, and he's a great father, a fabulous husband, and he's never at front of house, he always likes to be at the back.

In April 2021, Jack was one of the handful of royals who attended the private funeral for the late Duke of Edinburgh in Windsor, and later attended a service of remembrance for Prince Philip in March 2022.

Jack was also by Eugenie's side as she wiped tears away at her grandmother's The Queen’s funeral London and Windsor.

Until recently, they had been living as a family at Frogmore Cottage, the royal residence sub-let to them by Eugenie’s cousin Prince Harry and Meghan.

The couples are known to be close, with Eugenie and Jack becoming the first (and thus far, only) royals to visit the Sussexes in the United States.

In the meantime, Jack’s charm and discretion will be put to good use in Portugal, where it is rumoured that another privacy-shy couple may soon become their near-neighbours.

His old boss George Clooney and his human rights lawyer wife Amal - who organised Meghan’s baby shower in 2019 - are said to be interested in buying a property at the Costa Terra club.

Whether or not that comes to pass, you’ll surely not hear a whisper from Jack Brooksbank, who continues to live up to his reputation for being charming, discreet and an all-round safe pair of hands.