A sibling of this OG yachter turned royal got out of politics once it was discovered he was dating a transgendered woman.

He didn’t stop dating her though until he was about to be cut off the family money.

Jack Kelly Jr.

Grace Kelly, Princess of Monaco

Source: Mr. X via Crazy Days and Nights

The ‘scandalous’ romance that rocked Grace Kelly’s family

Grace Kelly may have been the only member of her family to marry a royal, but she wasn’t the only Kelly who dealt with public scandals.

Growing up in Pennsylvania, USA, Grace was raised alongside her three siblings; Margaret and John Jr., her elder sister and brother, and Elizabeth, who was four years her junior.

The four Kelly children, as well as their parents, were part of a small, close-knit Catholic community and were educated with traditional religious values.

Their background was part of the reason why Grace’s brother John, nicknamed “Kell”, ignited a family feud that blew the family apart when he began a love affair with a transgender woman.

John was a renowned womaniser when he met Rachel Harlow in the 1970s, while she was working as a hostess at a disco club she owned named Harlow’s.

Having already left his wife and five children in 1969 for a playboy life, John fell for Harlow and the two began a romance in 1975 that set the local rumour mill into overdrive.

Harlow had been assigned male at birth and completed gender confirmation surgery until 1972, after finding fame in the drag-show beauty circuit. – Source

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