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Diana Ross Begged Son Evan to Protect Her Estimated $500M Net Worth before He Wed Ashlee Simpson

Joe Akins
Jan 18, 2022
07:00 P.M.
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Hollywood icon Diana Ross's career has spanned over five decades. She is one of the most decorated artists of all time, thereby, one of the richest, and the singer has often been concerned with protecting her wealth.


Diana Ross's name can be mentioned amongst the best talents of the last century. Diana, 77, is an icon in the industry and has enjoyed several decades of success as a star in Hollywood.

As a teenager, Diana began singing with her friends and went on to join the pop/soul trio, "Supremes," a trailblazing 1960s group that had singles like "Come See About Me" and "You Can't Hurry Love." 

Ashlee Simpson, Evan Ross, and Diana Ross attend the 27th annual Elton John AIDS Foundation Academy Awards Viewing Party sponsored by IMDb and Neuro Drinks celebrating EJAF and the 91st Academy Awards on February 24, 2019 in West Hollywood, California | Photo: Getty Images


Diana Ross went solo in 1969 and went on to have many No. 1 hits with songs like "Ain't No Mountain High Enough" and "Love Hangover." She has weathered the test of time as a performer with a career spanning more than four decades, despite professional and personal highs and lows.

Diana also enjoyed a career as an actress and starred in many hit movies such as "Lady Sings the Blues," and "The Wiz." "Lady Sings the Blues" earned the "Thank You" star her first Oscar nomination.

She has received numerous honors, including a Golden Globe, a Tony, and numerous American Music Awards. As a member of the "Supremes," Ross was inducted into the Rock & Roll Hall of Fame in 1988.


Diana Ross performs onstage during "Motown 60: A Grammy Celebration" at Microsoft Theater on February 12, 2019 | Photo: Getty Images

The "I Love You" singer was honored for her dedication to the industry once more in 2000 when she received the Black Entertainment Television Lifetime Achievement Award.


With all of her awards and career success came great wealth. Diana's estate was valued at $500 million, and after a couple of failed marriages, she has become careful about protecting her wealth.



Diana's success was highly unmatched in the '60s. Except for the "Beatles," no other artist had more sales than her in the 1960s. Other stars like Beyonce and Michael Jackson named her as one of their strongest influencers.

Despite her success, Diana has had to endure a series of personal failures in her romantic life. The actress has struggled to maintain a love life and has been divorced twice.


Part of her failures has been linked to her success. In a 1979 interview with "People," Joel Schumacher, who directed Diana in "The Wiz," remarked that for the singer, her husband had to make more money than her or risk being the wife.

Although many people disagree with Schumacher's opinion, it is widely agreed that those who get too near to Diana find themselves in her shadow. 


Diana is willing to do all it takes to protect her wealth, even if it means disrupting her son's love life. The actress reportedly begged her son Evan to sign a prenup before marrying Ashlee Simpson. The doting mother made this plea to protect her fortune.

Diana was hinted that Evan had planned to marry his girlfriend without a prenup. She soon swung into action and asked her lawyers to draw up a 300-page agreement that would safeguard her estate. 



Sources maintained that without the prenup, the marriage was never going to hold. Although Ashlee comes from a well-to-do background, her wealth pales compared to what Evan would inherit.

Ashlee and her sister Jessica became popular stars in the early 2000s. Although their shine has long dimmed, they remain rich and fulfilled. The sisters have both focused on their family life and are mothers of three kids. Jessica now runs a fashion line while Ashlee while Diana's son Evan focuses on making music.

Ashlee reportedly has a net worth of $11 million, and Jessica is worth an impressive $200 million, a bulk which comes from her fashion brand, acting, and successful music career.



In an interview with the iconic show host, Larry King, Ashlee opened up on meeting Diana, her mother-in-law, for the first time. When asked how the icon treated her, Ashlee said, "amazing, she was very warm from the start."

The mom of three described how supportive Diana was in helping her find her rhythm when she was out of work for some time. According to her, the iconic singer was supportive and asked her not to be in a rush in getting back to her craft. This was a huge relief for the younger Simpson.

Evan added that Diana shares a strong connection with Ashlee. This claim was later confirmed when it was reported that the actress was present in the delivery room when her granddaughter Jagger Snow was born.



Before her marriage to Evan, Ashlee was married to singer, Pete Wentz and they share a son, Bronx. Ashlee had reportedly filed for divorce, citing irreconcilable differences. Wentz, on his part, did not want the marriage to end.

The rockstar had tried to persuade Ashlee out of the idea of a divorce, but her mind was made up, and she wanted to get out of their union. Following their divorce, Ashlee asked for spousal support and to be granted primary custody of their son while Wentz got visiting rights.


The couple did not sign a prenup. Days before their split was announced, the duo was spotted hanging out, and reports of their divorce came as a shock to their fans. Despite their split, Ashlee and Wentz maintained that they would remain friends. 

They were later spotted holding hands while enjoying family time. The former lovebirds even shared an affectionate tweet on social media, showing how well they were taking things.


Details of their divorce agreement were kept private, but reports emerged that it was a 103-page settlement agreement. Ashlee and Wentz have since moved on and started new adventures.

Life with Evan, her new beau, has been remarkable. The couple purchased a 6,250-square-foot, .44-acre estate in Los Angeles' Encino neighborhood for $4.5M while preparing for their third child.

The couple's farmhouse-style property has five bedrooms and six and a half bathrooms and is bordered by high hedges and a concrete gate.