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Sydney Holland Headed To ‘RHOBH’? A Look At Her Double Life With Billionaire Sumner Redstone

By Victoria Miller
Published on: 23:14 PST, May 31, 2016

Sydney Holland wants to be a Real Housewife. The 44-year-old ex-girlfriend of Viacom billionaire Sumner Redstone has formally pitched herself to join the cast of The Real Housewives of Beverly Hills for season 7, according to The Hollywood Reporter. A source told THR that Holland’s team created a promotional video for RHOBH casting executives, and if you think you’ve seen everything when it comes to RHOBH backstories, think again.

Sydney Holland spent five years with Sumner Redstone as his live-in girlfriend and gatekeeper to his daily schedule after she was introduced to him by Millionaire Matchmaker star Patti Stanger. But Sydney was ejected from the ailing 93-year-old media mogul’s Beverly Park mansion last fall after she was discovered to have had an affair with a former actor and ex-con.

During her time with Redstone, Sydney Holland co-existed with another Redstone companion, Manuela Herzer, to have a major influence on all aspects of his life. Both women were given millions of dollars by the former chairman of CBS and Viacom and they escorted him to parties. Holland was Redstone’s regular traveling companion, and she sat in with him on interviews. Sydney also invested in real estate with the millions of dollars given to her by her wealthy boyfriend. But Sydney Holland also used Redstone’s money to fly to Arizona on private jets to see her younger lover.

According to Vanity Fair, before her affair was discovered, Sydney Holland was given more than $60 million of Sumner Redstone’s fortune, much of which she invested in real estate. But several years into her relationship with Redstone, Sydney allegedly began an affair with George Pilgrim, a 49-year-old former actor who spent two years in prison on fraud and tax-evasion charges. Pilgrim lived in one of the houses Sydney Holland owned in Sedona, Arizona, and she flew there regularly to be with him, but she always flew home to Sumner Redstone’s mansion each night.

When Redstone found out about the fling in 2014, he ordered his longtime girlfriend and her two-year-old adopted daughter out of his life for good. An insider said every trace of Sydney Holland was removed from Redstone’s estate within two days.

“Sydney is out of his life,” the source said at the time. “It’s now, ‘Sydney who?’ There’s no f*cking with this man ever… If you mess with Sumner you are going to lose.”

George Pilgrim said that he had planned a future with Sydney before he found out the extent of her relationship with Redstone. In an interview with Vanity Fair, the former actor said he and Holland became engaged and started an in vitro fertilization process with the hopes of having a child together. They even started planning a nursery in the Sedona house.

When Pilgrim found out that Holland actually lived in Redstone’s mansion, she explained that they had a platonic relationship and that she flew back to Los Angeles every night to be his caregiver. Holland even said Redstone knew about her relationship with Pilgrim.

“[Sydney] told me that Sumner was her mentor,” Pilgrim said. “Sumner taught her a lot. Sumner was like a father figure to her. And she always represented it to me that she had power of attorney for his medical needs… It was never really represented that they had actually been in some sort of relationship. It didn’t make any sense, because he was so much older, 50 years older. It wasn’t logical to me.”

But when Sumner Redstone’s lawyers were informed about Holland’s relationship with George Pilgrim, Sumner went ballistic and kicked her to the curb.

For Real Housewives of Beverly Hills fans, the story of Sydney Holland’s double life makes the “Munchausen” storyline seem like small potatoes. And suddenly, Erika Jayne’s 32-year age gap with husband Tom Girardi seems awfully small.

Bravo and Sydney Holland have not commented on her Real Housewives pitch, but the show is reportedly cleaning house to make room for several new cast members for Season 7.

Take a look at the video below for more on Sydney Holland’s RHOBH pitch.

https://www.youtube.com/watch?v=P4sb9jqSheU

[Photo by Frederick M. Brown/Getty Images]

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