In the 27 years since Princess Diana’s passing, much has been written about the royal’s state of mind in her final months.

But few people were granted as close access to the late Princess of Wales as Tina Brown.

In July 1997, just two months before the tragic accident in Paris, the royal mother-of-two met the former Vanity Fair editor for lunch in New York with Anna Wintour.

Detailing their meeting in a personal essay for The New Yorker, Tina marvelled at the Princess’ ‘shrewd’ approach to public relations – an area she believes Meghan Markle is lacking in.

Earlier this month, the journalist appeared on The Ankler podcast – where she argued the Duchess of Sussex ‘has the worst judgement of anyone in the entire world’ and dubbed Megxit a ‘disaster’.

Pictured: Former Vanity Fair editor Tina Brown, who had lunch with Princess Diana just two months before her death in 1997

Few people were granted as close access to the late Princess of Wales (pictured in New York in 1997) as Tina Brown

However, this isn’t the first time Tina has taken aim at the Duchess of Sussex in public.

In 2022, The Diana Chronicles author accused the former Suits actress of ‘not understanding’ how hard her mother-in-law had to work to become a ‘humanitarian superstar’.

In her book The Palace Papers, an insider told Tina that Meghan ‘hated every second’ of her Australia tour in 2018 and claimed the visit was ‘pointless’.

Months later, the influential editor also said the Duke and Duchess ‘completely underestimated’ what life without the ‘palace platform’ would be like – arguing that Meghan lacks a defined ‘brand’ and instead latches on the ‘Twitter cause of the moment’.

Here FEMAIL takes a look back at how Meghan Markle lost a potential ally in one of Princess Diana’s most influential friends.

Meghan wasn’t prepared to ‘work like a dog’ like Diana? 

Two years ago, Tina Brown released her book The Palace Papers – where she delved into the fall-out of Megxit.

While promoting the book, the author claimed that Meghan ‘didn’t understand her role’ in the Firm during an appearance on ITV’s Lorraine.

The Diana Chronicles author accused the former Suits actress (pictured) of ‘not understanding’ how hard her mother-in-law had to work to become a ‘humanitarian superstar’

Tina Brown argued in 2022 that argued that the Duchess did not recognise the ‘great deal of very humdrum assignments’ Diana (pictured) undertook on behalf of the Firm before she became the icon she remains today

According to Tina, Meghan looked to the example of Princess Diana and thought that she could follow the same path.

However, she argued that the Duchess did not recognise the ‘great deal of very humdrum assignments’ Diana undertook on behalf of the Firm before she became the icon she remains today.

‘I think that was her fundamental sense of misunderstanding of what was going to happen when she joined the Royal Family – she saw the palaces and Diana as this global humanitarian super star, but forgot that for 16 or 17 years Diana worked like a dog within the Royal Family doing a great deal of very humdrum assignments.

‘It was her charisma she brought to the job that made her so extraordinarily special.’

The author said the couple made ‘bad choices’ and could have left the royal family on far better terms if they weren’t as ‘hotheaded’ when they made the decision to step back from their roles as working royals.