Sydney Holland sells in 90210 for $10.2 million to Obama’s financial advisor

One thing Yolanda loves about LA — and that really separates this city from NYC and other major metropolitian areas, we think — is that when it comes to LA’s wealthiest neighborhoods, the human element is so… vivid. No, Yolanda really hasn’t been drinking this morning. What we mean by that is that the rich areas are so diverse, not necessarily in terms of culture or ethnic backgrounds but through the means these residents utilized to became wealthy. Even New York City, melting pot though it may be, has mostly just financiers and foreigners in its most expensive buildings. Over here, it’s a decidedly more cacophonous mix, which could be good or bad, depending on one’s point of view. But it certainly makes for fun blogging.

For example, we have a wide assortment of folks from the entertainment world (sports, films, music, etc). Mix in a dollop of financiers and captains of industry, a splash of tech titans, and top it off with all those peeps who inherited family money. And then we have a squeeze of wild card —  those fun people who came into money through the backdoor, so to speak. Ahem.

Sydney Holland, the lady we are discussin’ today, belongs in that last category. She is a very wealthy woman, though she is not an heiress and she does not work. She made her money the old-fashioned LA way. Can y’all guess how?

That’s right! She hooked up with a rich old dude and sugar daddy-ed him out! Classic.

If that sounds a bit crass, Yolanda apologizes. But that’s really the truth, and the truth is rarely squeaky-clean. Our Ms. Holland is the ex-girlfriend of 94-year-old media tycoon Sumner Redstone, a guy who makes do with a net worth of $4.9 billion, according to the beancounters at Forbes.

Mr. Redstone — who has looked rather like an ambulatory corpse for the last 10 years or so — is a longtime resident of Beverly Park, an (in)famous enclave that is often considered to be the most exclusive and heavily secured guard-gated community in all of the United States. It is here, at Mr. Redstone’s $20 million mansion, where our story begins.

Sumner Redstone’s longtime Beverly Park mansion

Back in 2010, Ms. Holland was just another divorcée in her late 30s: deep in debt, driving an ol’ clunker automobile, and struggling to stay afloat in cold-hearted cesspool that is LA. She’d also had a bad luck for some time: she was a recovering alcoholic and her last boyfriend had died of a heart attack while she was having sex with him. (Egads!)

But Ms. Holland’s luck drastically changed when she met Sumner Redstone in 2010, after they were introduced by Millionaire Matchmaker Patti Stanger. The wily Ms. Holland worked her way through a sea of ladies vying for Mr. Redstone’s affection to become one of his two main girlfriends/companions. After all, if you’re a billionaire, why settle for just one significant other?

Over the next five years, court documents would later reveal, Mr. Redstone gave Ms. Holland (and his other lady friend Manuela Herzer) cash and gifts totalling more than $150 million. Ka-ching!

Sydney Holland (left) with Sumner and Manuela Herzer (right)

Though she was never married to Mr. Redstone, our Ms. Holland was reportedly set to inherit his massive Beverly Park mansion upon his death. That plan went south, however, after Ms. Holland was scandalously caught cheatin’ with an ex-con from Arizona and quickly banished from Mr. Redstone’s presence (and barred from entering Beverly Park). But that’s all a story for another day.

Anyway, Ms. Holland and Ms. Herzer wisely invested much of their hard-earned money into real estate. Manuela Herzer lives very near to Beverly Park in a huge mansion overlooking Mulholland Drive . And she also purchased multi-million-dollar homes in the 90210 area for all three of her adult children. We digress.

Meanwhile, Ms. Holland has proven herself to be a particularly shrewd (or maybe just lucky, we dunno) investor. Back in October 2013, if y’all recall the gossip headlines, she paid loopy pop star-turned-business tycoon Jessica Simpson $6,400,000 for a house in a famously celeb-favored 90210 enclave known as Hidden Valley. After making only cosmetic improvements, Ms. Holland sold that house only a year later for $8,225,000 to A-list actress Jennifer Lawrence.

The house that Ms. Holland bought from Jessica Simpson and sold to Jennifer Lawrence

After selling her Hidden Valley house, Ms. Holland decided to try out another gated community in the B.H.P.O. area. She ended up in the notorious Mulholland Estates, a heavily secured yet oddly crime-plagued area not far from Beverly Park. It should be noted that while the community does have a 90210 zip code (and thus residents list their address as “Beverly Hills, CA 90210”), the community is miles away from the actual city of Beverly Hills and is actually — technically speaking — geographically located in the hills above the San Fernando Valley’s Sherman Oaks neighborhood.

Ms. Holland’s Mulholland Estates mansion

Records show Ms. Holland paid $6,750,000 in July 2014 for her Mulholland Estates mansion, which is located at the very end of long (very long) cul-de-sac. Photos from the time she bought it show that the boxy, 1992-built Mediterranean mcmansion isn’t exactly inspiring or particularly attractive.

However, the crafty Ms. Holland gave the 7,166-square-foot place a freshening-up with the help of some snazzy new interior décor, including a bunch of astoundingly expensive art pieces by name brand folks like Jeff Koons, Retna, Andy Warhol, Lucien Smith, and Dan Colen. For more photos of her remodel, which was photographed last year by C Homeclick here.

There are also vintage limestone tiles in the entryway, polished hardwood floors in the formal living and family rooms, and the kitchen features top-of-the-line appliances.

The master suite shines with its whitewashed vaulted ceiling, an all-marble bathroom, and not one but two master closets, where Ms. Holland stores her multi-color collection of 28 Hermes Birkin bags, which start at about $10,000 a pop. And the backyard? Those are James Perse chaise loungers, which retail for a pretty penny indeed.

In July 2017, a Daily Mail story indicated that Ms. Holland was looking to sell her Mulholland Estates mansion for $8 million. So the stories go, she planned to move to Brentwood because her community homeowners’ association would not allow filming. And Ms. Holland was just dying to join Real Housewives of Beverly Hills! Can y’all imagine? “Oh bother, I have to sell my mansion because my darn HOA won’t allow me to film my silly reality show!

Anywho. Either Ms. Holland was being coy about how much money she would accept for her house or someone wanted this place very badly. Records show the house quietly transferred in late December (2017) — but not for anywhere near $8 million. Oh no. The place went for a whopping $10,200,000.

Yikes! That’s almost $3.5 million more than Ms Holland had paid only three years prior. And besides the interior decor, she only changed the pool and surrounding area!

So who is the big bucks buyer? Well, the house was purchased by a mysterious LLC with a Chicago (Illinois) address, but a little research makes clear that the new owners are a married couple named Robbie & D’Rita Robinson.

Mr. & Mrs. Robinson

Mr. and Mrs. Robinson may not be household names, but in certain well-heeled Chicago social circles they appear to be right proper superstars. Our Mr. Robinson is a former Goldman Sachs investment banker and is currently a managing director at BDT Capital Partners, a Chicago-based private equity firm that handles investments for high net worth individuals. For the last year or so, Mr. Robinson has been on leave from BDT, as he was hand-picked by former President Obama to advise him on investments.

Like her husband, Mrs. Robinson is a busy individual — she is a philanthropist and “social impact entrepreneur” who is also the founder and CEO of Chatty Guest, a free app that “encourages collaboration, mentorship and global dialogue across disciplines”.

Yolanda is not certain if the Robinsons — who are in their early 40s and have been married 14 years, FYI — plan to relocate to LA permanently or if this is just a vacation home, but we do know that their luxury condo in Chicago is currently on the market and has already undergone several price reductions.

The 3,157-square-foot unit sits on a lower floor in the historic Palmolive Building not far from Chicago’s Gold Coast. There are 3 beds, 3.5 baths, and lots of brown-and-white tones. The building includes numerous amenities: a full gym, two covered valet parking spots, a clubhouse, and an indoor sauna.

Yet even if the apartment transfers for its current asking price of $1,800,000, it appears the the Robinsons are facing a loss on this place: they bought it way back in early 2011 for $1,850,000. Somehow, however, Yolanda is fairly certain that the Robinsons will be just fine financially — no matter what the final sale price is.

Back in Mulholland Estates, the couple will have multiple celebrity neighbors within sugar-borrowing distance. Immediately next door to their new house is an imposing mansion that was once the residence of Shaquille O’Neal and is today owned by retired Japanese pop star Kiyusuke Himuro. Their other next door neighbor is big-time producer Mark Burg, and just two doors away is the home of Weezer frontman Rivers Cuomo.

Also in the same gated community are the abodes of Paris Hilton, Charlie Sheen, Christina Aguilera, Vanna White, Adrienne Maloof, Big Sean, DJ Khaled, Kendall Jenner, and at least one Saudi princess.

Listing agents (Chicago): Pamela & Cameron Sage, Baird & Warner


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