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Robert Redford met his first wife when they were still teenagers. Together for 27 years, the couple faced immense hardships, including two tragic losses.

The pair remained close despite their separation. However, the actor sparked mixed reactions from the public after it was revealed that he had found love again with someone 21 years his junior.

Robert Redford’s Rise to Fame and Retirement Regret

Redford’s path to stardom was anything but easy. He grew up as a scrappy kid known for stealing hubcaps in high school. The actor’s rebellious streak also cost him his baseball scholarship at the University of Colorado.

“I became the campus drunk and blew out before I could ever get going,” he recalled, reflecting on how he dropped out during his sophomore year. Despite his early troubles, Redford showed talent in caricature drawing.

This led him to pursue art seriously and embark on a year-long adventure around Europe. He lived the life of a painter, hitchhiking and staying in youth hostels. However, Redford soon realized his artwork was not original or good enough.

By the end of 1960, Redford made his Broadway debut, appearing in a series of plays, including the critically acclaimed “Barefoot in the Park.” The actor also gained experience in television and stage. This, plus his all-American good looks, quickly opened doors to film.

Redford’s career took off when he starred in “Butch Cassidy and the Sundance Kid” in 1969. The film solidified his status as a Hollywood star and set the stage for a series of successful films in the early 1970s.

1973 was particularly significant for Redford, with major hits like “The Way We Were” and “The Sting.” These films made Redford the number-one box office draw for the next three years. In 1980, Redford founded the Sundance Institute to nurture aspiring filmmakers.

The institute’s yearly film festival is now a major industry event. That same year, Redford made his directorial debut in “Ordinary People.” This earned him the Academy Award for Best Director a year later.

Despite this early success behind the camera, Redford waited eight years before directing another film. His second effort was the screen adaptation of John Nichols’ novel “The Milagro Beanfield War.”

In August 2018, after more than four decades of a successful acting career, Redford announced his retirement. The announcement came during the production of what he believed would be his final film, “The Old Man & the Gun.”

However, later that year, Redford expressed regret over this decision. “I think it was a mistake to say that I was retiring because you never know,” the actor stated. This gave hope to his long-time fans that he might continue to grace the silver screen.

Robert Redford’s Relationship with His First Wife: Triumphs and Tragedies

After returning from Europe, Redford spent some time in Los Angeles. There, he met Lola Van Wagenen, a 17-year-old Utah bank teller who lived in the same apartment building. Their connection was immediate, and the couple married in L.A. in 1958.

They moved to New York City, where Redford’s career flourished. Tragically, in 1959, Redford and his wife faced immense personal hardship. Their first child, a son, died at five months old from sudden infant death syndrome (SIDS). “That was a tough hit,” Redford said.

Despite their grief, the actor and his wife had to move forward. “We had to deal with it. You have to move on. And we had other children who came. But something like that doesn’t get completely dismissed,” Redford reflected.

The couple went on to have three more children. Their eldest daughter, Shauna, 63, became an artist and married Eric Schlosser, an author, in 1985. The ceremony took place on the lawn of her parents’ home in Provo, Utah.

The couple then welcomed a third child, their second son, James. James followed in his father’s footsteps and became a screenwriter and director after graduating from the University of Colorado.

However, his life was marred by severe health issues. He suffered from debilitating colitis, which led to cirrhosis, requiring a liver transplant in 1993. Unfortunately, the surgery did not go as planned.

While he was filming “Quiz Show” in New York City, Redford would fly every weekend to see James, who was waiting for another transplant. After a second operation and more complications, Redford revealed, “Now he’s fine,” in 1998.

Eight years after James was born, Redford and his first wife welcomed their second daughter, Amy. Amy also embraced the family’s cinematic legacy, becoming a producer, director, and actress.

She even landed a small role in “Maid in Manhattan” alongside Jennifer Lopez, Ralph Fiennes, and Natasha Richardson. Sadly, on October 17, 2020, the Redford family was struck with another tragedy.

James’s wife, Kyle, announced on Twitter that he had died following a bile-duct cancer diagnosis. “Jamie died today. We’re heartbroken. He lived a beautiful, impactful life & was loved by many. He will be deeply missed,” the tweet read.

“As his wife of 32 yrs, I’m most grateful for the two spectacular children we raised together. I don’t know what we would’ve done w/o them over the past 2yrs,” the tweet continued.

Redford remained close to his family in the wake of this great loss. A representative for the actor stated, “The grief is immeasurable with the loss of a child.”

After decades of marriage, filled with both unimaginable pain and shared triumphs, Redford and Van Wagenen decided to end their marriage. “I got lost for a time,” Redford admitted, reflecting on their separation.

Screenwriter Jeremy Larner noted that Redford never anticipated the split. “He told me he was totally faithful to his wife….They were very tight; they went through a lot of stuff together,” he said. Despite their divorce, as of 1998, Van Wagenen lived in Vermont, and the exes remained close.

Redford had a romance with actress Sonia Braga following his divorce. He also had a lengthy relationship with costume designer Kathy O’Rear, which ended around 1995. Eventually, the actor found love again with a woman over two decades his junior.

A New Chapter with Sibylle Szaggars

In 1996, after creating the Sundance ski resort, Redford met his second wife, Sibylle Szaggars, at the resort. “She’s a very special person. She’s younger than I am, and European, which I like, so that’s a whole new life,” Redford shared.

Szaggars is a German-born artist and is 21 years younger than Redford. Their relationship blossomed over the years and led to a 2009 wedding. The couple exchanged vows in an intimate ceremony at the luxurious Louis C. Jacob Hotel in Hamburg, Germany.

The wedding was a private affair, attended by 30 family members and close friends. According to reports, the bride wore a champagne-colored gown, while the groom donned a white suit.

In November 2015, Szaggars’s impressive career extended beyond the canvas when she founded The Way of the Rain. The non-profit organization focuses on raising public awareness and support for environmental protection through educational and artistic events.

In 2024, after 15 years of marriage, Szaggars, 67, decided to sell her home near Redford’s, 87, Sundance Resort. Reflecting on this change, Szaggars shared, “This home is truly near and dear to my heart.”

“It has been part of my story and a source of inspiration for my journey […]. I’ve relished in the sheer beauty of the setting, which is as serene and unspoiled as it is breathtaking,” she continued

Public Reactions to Robert Redford’s Much Younger Wife

The public has had mixed reactions to Redford marrying a woman 21 years younger than him. In 2012, the couple was spotted enjoying an outing in Berlin, Germany, and one person shared, “Not my cup of tea being married to a much older man. The thought horrifies me.”

“‘They both look their age.’ Many women married to much older men start looking older. Old husbands drag their younger wives down,” another person typed. A third commented, “Another wrinkled old geezer with a much younger woman.”

That same year, Redford and Szaggars attended the Venice Film Festival and another person praised the German artist for her appearance. “Mr. Redford’s wife looks very nice,” they wrote in part.

A social media user shared the same sentiment in 2017, tweeting in part, “I don’t mention her a lot but please know Sibylle Szaggars-Redford is hot.”

Despite the mixed reception from the public and having a significant age gap with his second wife, Robert Redford and Sibylle Szaggars’s relationship has flourished, showing that love can thrive at any stage of life.