If all-powerful movie star John Wayne can lose his life savings not once but twice to people he trusted, what chance do you have?
In a Watchdog tradition, every December I profile a prominent American who got snookered, looking for clues to how to make sure the same financial tragedy doesn’t happen to us.
I started in 2019 with my personal hero, Benjamin Franklin, who as a 19-year-old printer believed a British governor’s promises to set him up in a London print shop. Franklin never got a penny.

In 2020, I wanted to know if circus master P.T. Barnum actually said a sucker is born every minute. Turns out a competitor said that about him. Barnum said a customer is born every minute. Barnum lost half a million dollars in a failed clock factory scam. He filed for bankruptcy.

Last year, I studied the life of Dallas founder John Neely Bryan, Dallas’ first known white resident who also served as the town’s chief promoter. He didn’t get scammed. No, he did the scamming. He promoted Dallas as a great city to come and stay, but when travelers arrived they were stunned to see two small log cabins and a population of about 12. To lessen the sting, he offered every visitor free whiskey, bear meat and honey.
Manager for the stars
John Wayne’s final financial unraveling began with a 1965 shopping trip to the Neiman-Marcus store in Dallas. But I’ll get to that.

Let’s start during World War II when Wayne hired Bo Roos to be his business manager.
“With his hair slicked straight back, his mouth full of straight white teeth and his perfect tan, Roos was pure Hollywood,” write Randy Roberts and James S. Olson in their book John Wayne: American, which served as the basis for this story.

The husky blue-eyed man whose name was pronounced Boo was quick to smile and make a new friend. He gave off the aura of a European aristocrat. His car contained one of the very first mobile phones.
His clients included stars Joan Crawford, the Andrews Sisters and Marlene Dietrich, who recommended him. They were friends who drank together, went fishing and hunting and swapped stories. Wayne assumed Bo would protect his millions, maybe even make it grow.

Bo once said, “I’ve been called a gambler. … I’m only good for the client who wants action for his money.”
John Wayne may have been great as a Hollywood cowboy, but when it came to his money, he couldn’t shoot straight. Here he is in True Grit, for which he won an Academy Award.(Archives / AP)

Wayne first figured something was wrong when one of the investments Bo made for him attracted a slew of bounced checks and foreclosure notices. Wayne chewed him out, and Bo promised to improve Wayne’s cash flow.
The losses didn’t stop. Bo invested $700,000 in Panama. Wayne lost it plus a million more in that scheme.
As a major film star in the 1950s, he was broke. He found out when he and his wife ran up a $3,500 bill at Saks Fifth Avenue in New York. He told the clerk to charge it to Bo.
Three months later Wayne got an overdue notice.
“Bo!” he shouted, but it sounded like Boo. “Could you please pay the bill? I look like a [blankety] deadbeat.”
He sent his trusted secretary, Mary St. John, to Bo’s office, to check on his portfolio.
“Roos tried to stall her,” the authors write, insisting she come back at a more convenient time. But Mary was tenacious, demanding access to the file. When she saw it she was shocked. It was almost empty.
A few days later Wayne met with him and asked, “Bo, exactly how much money do I have?”
“Well Duke,” he said, using Wayne’s nickname, “not a great deal of cash.”
“Just tell me how much money I could raise if I had to.”
“That’ll take a couple of weeks,” Bo said.
When they met again, Bo still couldn’t answer.
Wayne slammed his fist on Bo’s desk and shouted, “I’ve given you a [blankety blank] fortune over the years. It’s a simple question.”
Without looking him in the eye, Bo confessed. “It’s all gone.”
Accountants who later checked the books declared that Bo didn’t steal it. He lost it through “gross mismanagement.”
Wayne wasn’t the only one. Like Wayne, Red Skelton didn’t check his financial statements, schedule in-person meetings and personally inspect investments. That was their undoing.
An arbitrator advised Wayne not to go to court because the publicity about his don’t-ask-questions style would make him look like a “complete ignoramus.” Plus, Bo was bankrupt, too.
“Just forget about it and start all over,” he advised.
A second time
Wayne wanted a manager whom he could trust. He decided to go with his son-in-law Don LaCava. His job: Invest conservatively and don’t lose money.
On that fateful 1965 trip to Dallas, Wayne, who treasured his annual Neiman-Marcus catalog, spent $30,000 at that store and others.
When the bill came, his son-in-law chewed him out: “How could you spend so much money? You don’t have this kind of money in the bank. How am I supposed to pay these bills?”
Wayne reminded he had given him millions. “There better well be money in the bank to pay these bills.”
LaCava had invested in bad real estate, dry oil wells and more.
Wayne fired him.
It was getting to be a thing.
Bo’s 1973 obituary in The New York Times mentioned “his cold blue eyes and pencil mustache,” but not that he lost his clients millions. Although there was a brief mention of ventures “not all of which were successful.”
With both men, the No. 1 movie star didn’t check his financial statements, schedule in person meetings and personally inspect investments. Do you?
John Wayne made about 200 movies, and he was usually paid handsomely. But he didn’t watch his money managers like a hawk, and they left him with birdseed.(Archives / AP)