After O.J. Death’s His Daughter Sydney Brooke Simpson Breaks Silence

O.J. Simpson's daughter Sydney Brooke Simpson has built a splendid career in the world of real estate.

By Chakku HaruPublished on: April 7, 2024 Updated on: May 6, 2024
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Many are familiar with O.J. Simpson‘s trial and his controversial acquittal in the murders of his former wife, Nicole Brown, and her friend, Ron Goldman. Following a minimum sentence, Simpson was paroled on July 20, 2017, and released on October 1. However, the story of his daughter, Sydney Brooke Simpson, remains lesser-known.

After O.J.’s trial, many of you may have been curious to know what happened to his daughter, Sydney. She has carved out a successful path for herself by establishing an impressive real estate portfolio in Florida. Together with her younger brother, Justin Ryan Simpson, Sydney has developed a mini-real estate empire in St. Petersburg. She is now also a mother to a child. 

The article below includes other intriguing details about her life, from an arrest in high school to her prominence in the real estate sector and her remarkable weight loss journey.

Profile Summary

Date of Birth October 17, 1985
Age 38
Zodiac Sign Libra
Ethnicity Afro-American
Nationality American
Religion Christianity
Height 5ft 8in (1.73m)
Weight 68kg
Net Worth $1.5 million
Hair Color Brown

Sydney Simpson Stepped Out in St. Petersburg With a Baby and Male Companion After Father’s Death

In late April 2024, Simpson emerged in public, a sight not seen in nearly six years, just days following the cremation of her father, O.J. Simpson. Photographed in St. Petersburg, Florida, Sydney appeared composed as the celebrity kid handled a child’s car seat outside her residence. It was her first public appearance since her father passed away from prostate cancer earlier this month on April 10, in Las Vegas.

Sydney and her partner in Florida.
Sydney Brooke Simpson is carrying a baby with her seemingly partner. (Image: Daily Mail)

Dressed casually, Sydney, a successful realtor, was accompanied by a male companion, likely her partner and the father of her child, as they set off to run errands.

She Now Runs a Real Estate Business in Florida

Simpson is the founder of Simpsy Properties, LLC. Her brother Justin is also a real estate agent and they have been active in the field, particularly in St. Petersburg, Florida since the mid-2010s. Simpsy was officially incorporated on September 11, 2014. It has amassed over 13 properties by 2017, primarily in low-income areas, with purchase prices ranging from $35,000 to $215,000.

O.J. Simpson, Nicole, Sydney and Justin.
With her parents and a brother. (Image: Getty)

The Simpson siblings have built a substantial portfolio, with properties acquired mainly in cash.

Their real estate dealings, managed through various limited liability corporations, include a range of properties from single units to multi-unit buildings. For example, Sydney’s company Simpsy acquired properties at prices like $35,000 and $47,500, while Justin’s LLC purchased a duplex for $95,600 and a building for $215,000. Some of these transactions involved properties bought and then sold within their network.

Interestingly, one of the properties was initially bought by Sydney’s boyfriend, Robert Blackmon for $38,800 in 2014, and later sold to Justin.

Meanwhile, Tenants were surprised to learn that the Simpsons owned their properties. Carmen Gorton, a resident on 47th Avenue, expressed her astonishment to the New York Post, saying, “I had no idea,” upon discovering the identity of her landlords.

Apart from her emerging real estate business, her LinkedIn profile suggests Sydney also serves as the vice president of J.M.I. Investment Properties, LLCJ since 2014. Further, she had a separate role as a special events manager at Canoe Restaurant in Atlanta in 2010.

She Leads a Life Of Solitude

Currently, Sydney leads a secluded life in St. Petersburg, Florida. She resides in a modest ranch-style home. She bought her home for $100,000 in 2015, and it’s only a 10-minute drive from “Pedophile Park,” a community where child sex offenders reside.

Her only companions are her three dogs. Neighbors characterized her as very private and mostly isolated. “She’s very quiet,” one neighbor told the RadarOnline. “She lives by herself, and doesn’t have many friends.”

Previously, she shared an apartment in Miami with her brother, Justin. However, their paths have diverged, with Justin now living 250 miles away in Tallahassee.

In May 2018, RadarOnline found some troubling details about Sydney’s current lifestyle. They caught her carrying a large Jose Cuervo tequila bottle and a 12-pack of Rolling Rock beer to the trash at her old Florida house.

Sydney was spotted with empty drink bottles at her Florida home.
(Image: RadarOnline)

She Arrested for Disorderly Conduct at Her Brother’s Basketball Game

In Jan 2005, Simpson was arrested for getting into a fight and displaying disorderly conduct at her brother Justin’s varsity basketball game in Miami. The incident occurred at a match between Gulliver Preparatory School, Sydney’s alma mater, and its rival Ransom Everglades School.

Miami police were called to the scene where Sydney, then aged 19, became aggressive and used swear words towards the officers. She even slapped one during her arrest.

During the altercation, two teenage girls reported to the police that Simpson had struck them in the face. However, they chose not to pursue legal charges.

Later on, she was charged with misdemeanors for disorderly conduct and resisting arrest without violence. These charges could result in up to a year in jail and a fine of $1,000.

She then signed a notice to appear in court on the misdemeanor charges and was released without having to post bond.

Yale Galanter, Sydney’s attorney argued the situation was overblown and claimed the police exacerbated the situation.

“After the police were told that nobody wants to press charges . . . Sydney is arrested for disorderly conduct?” Galanter told the Post.

After graduating from Gulliver, Sydney went on to pursue a higher education at Boston University. She earned a Bachelor of Arts in Sociology from the university’s College of Arts and Sciences in May 2010.

Reunion With Her Late Father O.J. Simpson During the 2018 Thanksgiving in Florida

In November 2018, O.J. Simpson was seen celebrating Thanksgiving with his children in St. Petersburg, Florida. It was his first trip out of Nevada since his parole. He was with his children, Justin, aged 30, and Sydney, aged 33. This occasion was special as it was their first public appearance together since they were children in 1994.

Sydney and Justin enjoyed a meal at a waterfront seafood bar and grill in Tierra Verde.

O.J. and Sydney Simpson at waterfront seafood bar and grill in Tierra Verde.
Sydney with her dad O.J. outside St. Petersburg. (Image: DailyMail)

Their reunion was filled with light-hearted moments, as O.J. engaged with other diners and took selfies with fans on the beach.

However, the backdrop to this family reunion is a history marred by tragedy and legal drama. Simpson, a former NFL star and Heisman Trophy winner was acquitted in the infamous 1994 murder case of his ex-wife, Nicole Brown.

Following her death, a prolonged custody battle ensued between O.J. and Nicole’s parents over Justin and Sydney, who were both under ten years old at the time of their mother’s death.

It was only after O.J.’s acquittal, that they were allowed to move with him to St. Petersburg, where they were raised.

Additionally, O.J. had three children from a previous marriage to Marguerite L. Whitley. They are Arnelle L. Simpson, Jason Lamar Simpson, and Aaren Lashone Simpson. Tragically, the youngest, Aaren, was only two years old when she drowned in a family swimming pool in 1979.

In fact, Sydney Simpson’s parents, O.J. and Nicole, were divorced before Nicole’s tragic death. The couple married in 1985 and initially enjoyed a few years of happy marriage.

However, their relationship deteriorated in the late 1980s, leading to Nicole filing a lawsuit against O.J. for abuse in 1989, to which he pleaded no contest. By February 25, 1992, Nicole had filed for divorce.

Sydney Brooke Simpson College Sweetheart Says She Didn’t Believe Her Dad, O.J., Murdered Her Mother

Brooke was just eight when her mother, Nicole, was killed, with her late father, O.J. Simpson, as the primary suspect. Despite the tumultuous years that followed, Sydney has maintained a private life. Her ex-boyfriend, Stuart Alexander Lee, shared insights with in June 2019, praising her strength and work ethic.

“Sydney is a real good girl and she has a good head on her shoulders,” Lee told Radar. “She’s not lazy. She works very hard.”

The former couple met at Boston University and later moved to Atlanta, where Sydney worked as an events coordinator at luxurious Atlanta restaurant The Canoe. They were in a relationship roughly from 2007 to 2012.

Lee noted Sydney was reluctant to publicize her life or opinions on the murder, emphasizing her fear of fame and its repercussions.

“When I was with her, I got friends in the industry I tried to set her up with and she said fame is a scary thing. It’s so real to tell your side of the story,” Lee added.

Privately, she doubted her father’s guilt, suspecting other scenarios like a botched drug deal.

“She talked about the murders, of course. Of course she talked about it. The way she feels, she doesn’t feel like he did it,” Stuart said. “They speculate that it was a drug deal gone bad. Sydney doesn’t believe O.J. did it, but she doesn’t know what to believe.”

Lee and Sydney’s relationship ended due to his music career demands. But, he holds no resentment, wishing her the best and hoping she might one day share her story to inspire others and vindicate her family.

At last, Stuart said, “She’s a good-looking girl, the whole nine. She’s hella strong.”

Stuart, also known as Stu Lee, is a Southern-born American rapper.

She Also Dated St. Pete Council Candidate Robert Blackmon

In December 2014, Sydney and her former boyfriend Robert Blackmon were first seen together leaving the upscale Mr. Chow’s in Los Angeles. They met through her younger brother Justin after the two men became friends at Florida State University.

Simpson and her former boyfriend Robert.
Sydney and Robert. (Image: RadarOnline)

Fast forward to July 2017 in St. Petersburg, where Blackmon, running for City Council, found his personal life under scrutiny.

Despite this, Blackmon remained committed to focusing on the political issues, urging the public to prioritize the electoral agenda over his personal life.

He also acknowledged the support of his girlfriend Sydney and said to the New York Post, that she is a “very private person.”

“She’s been selflessly supporting me and not worried about herself,” he added.

However, Blackmon later denied he was dating Simpson. He said Tampa Bay Times, “She’s a good friend of mine, but we’re not dating.”

Simpson’s Transformative Weight Loss Journey

Over time, Sydney’s weight loss journey has seen dramatic fluctuations. She struggled with her weight in high school, slimmed down significantly by 2004, but gained weight again by 2014. Despite a stable weight phase around 2016, her sedentary lifestyle and alcohol use posed challenges.

By 2024, Sydney achieved a significant transformation, shedding weight from 200 to 150 pounds.

The Striking Resemblance Between Sydney and Khloé Kardashian

The debate over whether O.J. was the biological father of Khloé Kardashian was reignited after the premiere of “O.J. Simpson: The Lost Confession?” on Fox on March 11, 2018.

Sydney and Khloé Kardashian
Sydney Simpson and Khloe Kardashian.

Viewers couldn’t ignore the striking resemblance between Khloé and Sydney, fueling further speculation about Khloé’s paternity. This theory has been around since Ellen Pierson, a former Kardashian step-mom, claimed that Robert Kardashian, Khloé’s supposed father, confessed that Khloé was not his biological child before his death in 2003.

Despite the persistent rumors and the opportunity to clarify her parentage with a paternity test, Khloé has chosen not to. Kris Jenner and O.J. had both denied the allegations.


Has Sydney Brooke Simpson Changed Her Name?

According to some online reports, she changed her name to Portia to hide her real identity.

About Author: Chakku Haru

Chakku, a seasoned celebrity content writer with a profound passion for the entertainment industry. With years of experience in the field, Chakku specializes in capturing the essence of actors, singers, YouTube stars, and journalists. His expertise extends to providing in-depth insights into their lives, from their career milestones to personal anecdotes that resonate with fans worldwide. Through his captivating writing, Chakku brings the stories of these luminaries to life, leaving readers inspired and engaged