Barbara Walters Was ‘Very Regretful’ About Strained Relationship With Daughter Jackie: ‘She Couldn’t Fix It’ (Exclusive)

Towards the end of Barbara Walters’ incredible career, she’d often ask her friends if she could see pictures of their children and grandchildren, with a sort of wistfulness, telling them how lucky they were to have big, happy families.

“She’d tell everyone, ‘I so admire your relationship with your children,’ ” her longtime friend, former NBC correspondent Cynthia McFadden, tells PEOPLE in the latest issue. “She was very regretful about her family life. It was something she felt like she couldn’t fix. So that was really tugging at her.”

In the upcoming Hulu documentary Barbara Walters Tell Me Everything (June 23), director Jackie Jesko explores Walters’ rise to the top, becoming the first-ever female nightly news anchor in 1976, and then the undisputed queen of the celebrity sit-down interview. Jesko also examines the toll her demanding career took on her personal life, without making it the focus of the movie.

“I grappled with that,” Jesko says, of wanting to make sure Walters’ regrets about not being a better wife and mom didn’t overshadow everything she did accomplish successfully throughout her remarkable career. “I do feel like if she had to do it all over again, she probably wouldn’t change a thing.”

Walters became a mother in 1968, when she adopted her daughter Jackie with her second husband, Lee Guber, after suffering three miscarriages. At first, it seemed like she had it all. In the film, Walters can be heard via archival footage saying of motherhood, “My world came together. I mean, I was already on the Today Show. And I’d had three miscarriages, and now I had everything.”

But it proved to be an impossible balancing act. Walters was not only an ABC News anchor, but her Barbara Walters specials, where she sat down with everyone from political figures like Fidel Castro and Ronald Reagan to the biggest stars of the day, including Barbra Streisand and Clint Eastwood, were incredibly well-received.

“Barbara was always flying somewhere, interviewing someone,” McFadden says. And it’s not like she could have brought her young daughter along for the ride.

“Today, people are more accepting. You can bring your kid to the office. In those days, if I had brought Jackie into the studio, it would be as if I had bought a dog who was not housebroken,” Walters herself can be heard saying in the doc,

As Jackie grew older, she and Barbara butted heads, and as a teen, Jackie became a drug user and a runaway and was eventually sent to a boarding school for troubled kids, which she’s said straightened her out.

But the relationship remained strained. McFadden says it was difficult for Walters to relate to someone who wasn’t as career-driven as she was: “She couldn’t understand someone like Jackie, who wasn’t racing to the top.”

“They were just so dispositionally and physically unlike each other,” she continues. “It was a struggle. That’s not to say they didn’t love each other, but it wasn’t what she’d hoped for, and probably not what Jackie had hoped for either. “

She adds, “I think it’s important to say that Jackie shouldn’t be held accountable for any of this, and Barbara wouldn’t have wanted her to be. I think this [struggle] was really on the adult side of the equation here. Jackie is a delightful person.” (These days, Jackie stays firmly out of the spotlight.)

McFadden, who was also adopted, recalls a segment she did on adoption, where she had the chance to interview Jackie.

“I asked her, ‘What was harder, being adopted or being Barbara Walters’s daughter?’ ” McFadden recalls. “She immediately answered, ‘Being Barbara Walters’s daughter.’ ”