Diana Ross Begged Son to Protect her Estate – His Life Changed Following Wedding

• 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's son is now married and has given her two grandchildren, who are "in awe" of the singer.

Diana Ross's name can be mentioned among the best talents of the last century. Now 79, she 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 released singles like "Come See About Me" and "You Can't Hurry Love."

The singer went solo in 1969 and went on to have many No. 1 hits like "Ain't No Mountain High Enough" and "Love Hangover." She has stood 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," Diana was inducted into the Rock & Roll Hall of Fame in 1988.

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 in the upper millions, and after a couple of failed marriages, she has become careful about protecting her wealth. Her worries about money have even filtered down to her children.

Concerned about Her Wealth

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

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

The iconic songstress 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 allegedly made this plea to protect her fortune.

Diana received a hint 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.

Family Ties and Millions

Sources maintained that without the prenup, Evan's marriage was never going to hold. Although Ashlee comes from a well-to-do background, her wealth pales compared to what he 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 and Diana's son Evan focus on making music.

Ashlee reportedly has a net worth of $11 million, and Jessica is worth an impressive $200 million, the bulk of which comes from her fashion brand, acting, and successful music career. Luckily for Evan's wife, his mother has been very welcoming to her.

Meeting Diana

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 to get back to her craft.

This was a huge relief for the younger Simpson sister. Evan once claimed 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. When Ashlee was married to her first husband, they did nothing to protect their individual wealth.

No Prenuptial in Ashlee’s Previous Marriage

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

The rockstar 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 Pete got visitation 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 Pete 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.

More about Evan and Ashlee’s Lives and the Bond Their Children Have with Diana

Ashlee and Pete 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. Speaking about her husband, Ashlee once revealed that their "strong relationship" was created long before they married in 2014, and it gave them good grounds for their marriage.

The "Pieces of Me" singer feels that her friendship with Evan is deep and amazing. Diana's son went out of his way to surprise his wife and sometimes took her to do fun activities, with the moments allowing them to leave their parental roles and connect.

In June 2023, Evan revealed that Jagger, eight, and Ziggy Blu, three, are "in awe" of his legendary mother. The 34-year-old also shared how the kids loved seeing their grandmother perform at her concerts. Speaking about his mother, Evan said she didn't do anything other than for love.

He shared that Diana doesn't do things for money but only for love. The star's son also noted how the songstress cares about her children, grandchildren, and people in general. Evan also lovingly called his mother beautiful.