EXCLUSIVE: Prince Harry's Shocking 'Near Fling' With Kate Middleton 'Is REAL Reason Behind His Bitter Rift With Future King William'
Prince Harry's rumored near fling with Kate Middleton allegedly fueled his feud with brother Prince William.
Nov. 13 2025, Published 8:26 p.m. ET
Prince Harry's past bond with Kate Middleton has been thrust back into the spotlight, with insiders telling RadarOnline.com their once-close relationship – and William's jealousy over it – is one of the hidden drivers behind the brothers' bitter estrangement.
Nearly two decades after Prince William briefly split from Kate in 2007, former royal staff and palace sources say the dynamic between Harry, now 41 and Kate, 43, was far deeper than the public realized.
'Near-Fling' Speculation Sparks Royal Tension
Insiders said Harry and Kate once shared a close bond that made William jealous.
One former royal aide insisted the pair had a "near-fling," and said William has never fully been able to get rid of his jealousy over it.
A source said: "The tensions it created still echo in the present-day breakdown between the once-inseparable princes."
The renewed conversation began after Grant Harrold, former butler to King Charles, recalled William and Middleton's 2007 break-up in his book The Royal Butler.
He said about Harry and Middleton: "They got on so well. I remember, when Prince William and Kate separated – you know, Prince Harry and Kate got on so well that I even thought that maybe Harry and she would get together."
He continued: "They were that close. They were best friends, and I wouldn't have put it past Harry thinking, 'Well, she's a pretty girl, My brother didn't want her. I'll have her.'
"That wouldn't have surprised me at all. So it could have been Harry and Catherine easily, I would have thought. But, you know, thankfully William got her back. What I'm trying to say is, that is how close they were."
Harry and Kate's 'Natural Ease'
A former palace aide said the bond between Harry and Middleton was widely acknowledged.
A senior royal source said the remarks "hit a nerve" because "everyone inside the family knew Harry and Kate shared a natural ease with each other that William sometimes struggled with."
A source said: "William has always been more guarded, while Kate and Harry clicked instantly. People noticed it – including William. When they split, he knew there was a tiny window where anything could have happened."
Another insider went further, claiming Harry and Middleton's easy rapport "created complications long before his future wife Meghan Markle ever entered the picture."
The insider said: "William would never admit it, but he hated the idea that Kate and Harry might have worked as a couple. It was a jealousy that wasn't romantic – it was about loyalty, attention, the fear of being overshadowed."
A former palace aide, who worked with all three at the time, said the bond between Harry and Middleton was widely acknowledged.
"They were genuinely close – laughing, teasing, finishing each other's jokes. You could see why Harrold thought it was possible. And you could see why William didn't like the speculation. It planted a seed that never really went away."
Kate Was the 'Bridge' in the Trio
William reportedly feared Harry and Kate’s friendship stole attention from him.
Those close to Harry say his relationship with Middleton was one of the great lasting casualties of the royal rift following his 2018 marriage to Markle, now 44, and the couple's 2020 departure from royal duties.
One friend of Harry's said: "Kate was like a sister to him. Losing her in his family estrangement was more painful than losing William in the feud. He blames the palace dynamics – but William's lingering jealousy about Harry's link to Kate has as much to do with their ongoing estrangement as Harry's betrayals of the royal family as an institution."
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Insiders said William never forgot how close his brother once was to Kate.
Another royal insider said: "It's no coincidence the brothers' relationship deteriorated fastest once Harry felt pushed out of that trio. Kate was the bridge. When the bridge went, everything fell apart."
As for William, 43, a longtime royal associate said: "He's protective, he's proud, and he remembers history." And history, for him, includes a moment when his future wife and his brother were very, very close – maybe far too close for comfort."
