Cindy McCain: Daredevil With a Big Heart

An intimate look at a complex and talented woman with deep empathy for children.

Oct. 3, 2008— -- According to one family friend, Cindy McCain is Arizona: born and bred.

"The big skies, the sunset, in a way, the need to be independent and strong as a woman, and I think Cindy inherited that spirit," said real estate developer Sharon Harper, who has known Cindy for decades.

Cindy McCain's father Jim founded Hensley and Co., Arizona's largest distributor of wholesale Anheuser-Busch beer, and the third largest beer distributorship in the United States.

He had children from a previous marriage, but he and Cindy's mother left her almost all of his reported $100 million fortune, as well as his love of outdoor adventure.

Click HERE to watch Diane Sawyer's "Portrait of a President"

Great Adventures a World Away

Cindy McCain, 54, describes her father as a "cowboy" who also loved race cars. She does, too. The former Junior Rodeo Queen has even mastered "drifting," a technique used by race car drivers. The high-speed thrill sport requires making sure that the front wheels of the race car are pointed in the opposite direction of the turn, which causes the rear wheels to skid. The technique originated in Japan, and is often used in competition to maintain speed after "drifting" through a turn.

She's also deeply involved in charity work. At the Republican National Convention, Cindy McCain was near tears when others praised her work, bringing medical supplies to developing and war-torn countries.

In seven years, she led more than 50 missions abroad as part of her charity, American Voluntary Medical Team. She continues to volunteer her time in developing countries and works with Operation Smile, a nonprofit, founded by a plastic surgeon, that performs operations on children with facial deformities.

"There's always at least 300, 400 children, all with these gaping holes in the lip and roof of their mouth, but she's right down there with them," said Dr. Bill Magee, who founded Operation Smile in 1982.

Cindy also contributes her time to the Halo Trust, an organization Princess Diana worked with that's dedicated to the eradication of landmines.

It's a world away from the sprawling ranch house where she grew up -- and from a life in which her college car was a Porsche -- and, later, a Mercedes. But it wasn't always that way.

"Well, in the early years, we didn't have," Cindy McCain said. "He and my mother started out with absolutely nothing, scraped together everything they could just to be able to start the business, and sold everything they had, also. And it wasn't until later on that they really started to do really well ... that we could be described as someone that 'had money,' as you put it."

Cindy McCain considers her father's company a legacy to be handed down to her own family.

"He worked very hard, and my name is on that building where my father worked and built. And so, to me, it means I have a great deal to live up to," she said.

As a college student, she resisted the pressure to join the big family business, instead choosing to earn a master's degree in special education. Soon after graduating, she began teaching at a school in Avondale, Ariz., working with disabled children.

Meeting John McCain

After a year of teaching, she went to Honolulu on vacation with her parents. They attended a Navy cocktail party, and a stranger wearing a captain's uniform approached her.

"He kind of followed me around the room a little bit," she said, laughing. "And as the night went on, we finally started to talk then, and he asked me to join him for a drink at the Royal Hawaiian Hotel, which, if you've ever been there, you know it's a perfect setting."

She was immediately drawn to his wit. "What I noticed first when I really sat down with him was his humor and his intelligence," she said. "And he was so different from anybody I'd ever met. I also couldn't imagine why he had the least bit of interest in me, because I was so much younger."

John McCain was 18 years her senior. She was only 24 at the time. But they both lied about their age. He said he was four years younger and she said she was four years older.

The following year, they married, shortly after McCain divorced his first wife, Carol.

It was only after getting their marriage license that they found out each other's true age, a revelation Cindy said "didn't matter to either one of us."

When he was a single Navy pilot, McCain had famously gotten the beautiful girls, including a model from Rio de Janeiro. In flight school, McCain drove a Corvette and, according to McCain's friend and former Tennessee Sen. Fred Thompson, McCain dated "a girl who worked in a bar as an exotic dancer under the name of Marie, the 'Flame of Florida.'"

John McCain took her to a proper party attended by Navy wives. "She was in a lovely green velvet dress that I'd seen her dance in a couple of times, some of the wives got their noses a little bit out of joint," McCain's friend Adm. Chuck Larson said.

John McCain said, "It was a bit of a cultural shock there. But it was all in fun."

Twenty years later, he was in love with Cindy Hensley. John McCain has since written in one of his books that she made his successes and defeats less important than his happiness with her at home.

Click HERE to watch Diane Sawyer's "Portrait of a President"