Book Excerpt: A Crooner, Caddies & Kings

December 09, 2016

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Bing Crosby, or dad to me, was the most popular entertainer in the world in his day, a day that lasted the better part of five decades. In 1977, the last year of his life, he was still selling out shows in London and New York City. "Just imagine something five times stronger than the popularity of Elvis Presley and the Beatles put together," Tony Bennett said in 1999. Dad's influence spanned generations. The Beatles' first hit single, "Please Please Me," was inspired in part by a line in one of Dad's songs.

"I remember the day I wrote it," John Lennon said. "I heard Roy Orbison doing 'Only the Lonely' or something. And I was intrigued by the words to a Bing Crosby song that went, 'Please lend a little ear to my pleas.' The double use of the word 'please.' So it was a combination of Roy Orbison and Bing Crosby."

Billboard called Dad "the most popular radio star of all time." For five years in a row he was the No. 1 box-office draw, and in 1944 he won an Academy Award as best actor for his portrayal of Father O'Malley in "Going My Way."

He ranks among the best-selling recording artists in history with more than a half billion of his songs and albums in circulation. His recording of "White Christmas" is the best-selling single of all time. Generations have been bridged by this voice, which The Times of London once wrote had been "heard more often by more people than that of any mortal in history." Between 1927 and 1962 he had 368 charted records. No one else is even close: Frank Sinatra had 209, Elvis Presley 149 and the Beatles 68.

Yank, a weekly military magazine published during World War II, identified him as the individual who had done the most to boost morale during the war, according to U.S. troops polled; President Franklin Roosevelt came in second. When Dad arrived in London, the Office of Strategic Services thought it might be a good idea for him to broadcast directly to the German people. Thus the moniker Der Bingle was conceived. At one point Dad was in France, where there was still fighting, and was invited to Gen. Omar Bradley's headquarters. The general asked Dad where he'd been that day.

"We made it to the town of St. Mère Eglise," Dad said.

"St. Mère Eglise?" Bradley said incredulously. "We haven't taken St. Mère Eglise yet!"

"Well, we had it for a while this morning," Dad said in his best deadpan. "I can't believe that you've lost it already."

And then there was golf. Everything Dad accomplished in the entertainment field was a distant second to this game that animated him more than anything else. As my mother, Kathryn, so aptly described many years ago, Bing Crosby was a golfer who sang.

"In the battle against par or against your opponent," Dad once told Golf Digest, "you can't think about much else, and the result, for me at least, is good therapy. For me, golf has been a kind of passport to relaxation and happiness."

He began the Bing Crosby Pro-Am in 1937; and it still is played today, though under an assumed name, the AT&T Pebble Beach Pro-Am. The pro-am concept that is a staple of virtually every PGA Tour event today, with proceeds earmarked for charity, was Dad's idea. One's standing in the social strata was of no concern to him. He was as comfortable with caddies as he was with kings, a man who could mix and match with the Rockefellers, Vanderbilts and Mellons as well as caddies and railbirds likely to be betting their dinner money on their next favorite horse.

"As long as a person was bright or amusing or congenial, it mattered little to Crosby how wealthy or socially prominent he might be, and his friends included studio technicians, musicians, chauffeurs, horse trainers, and proprietors of bowling alleys," Herbert Warren Wind wrote in The New Yorker.

On the wealthy front was George Coleman, my father's best friend. Coleman was an Oklahoma oil man among other varied financial interests and an avid golfer, who counted Ben Hogan among his closest friends in golf, as did my father. The original Mrs. Coleman once was heard saying to her husband, "You're not going to invite any of those golf-pro friends of yours to our party tomorrow night, are you?" The future ex-Mrs. Coleman was the antithesis of my father, and she was forever dubbed "the former beloved" by Coleman after they divorced. Dad's nephew, Howard Crosby, told an illuminating story about my father's lack of what the British journalist Alistair Cooke called "prima donnaism." It occurred in 1975, a few days before the contestants in the Bing Crosby National Pro-Am were set to arrive.

The Office of Strategic Services thought it might be a good idea for him to broadcast directly to the German people. Thus the moniker Der Bingle was conceived.

"Uncle Bing showed up in town and called to see if I wanted to meet him at Cypress [Point] for a bit of golf the next day," Howard said. "Of course I was up for that, so we planned to meet at the pro shop at 7:30 the next morning. When I got there, Uncle Bing was already sitting on the trunk of his car, changing into his golf shoes. Then he asked the assistant pro if there were any caddies who could play a bit. And [the assistant pro] said there were a couple of single-digit handicappers back there. So Bing hired the two kids to fill out a foursome, plus two more to carry bags, and away we went. I remember thinking at the time that there were undoubtedly hundreds of the wealthiest, most prominent citizens of Carmel/Pebble Beach who would have loved to be in that foursome with Bing Crosby, and here he goes and hires a couple of caddies. How typical of Bing."


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Dad's principal playground during his years in Los Angeles was Lakeside Golf Club, an entertainment-industry enclave then and now: from Oliver Hardy, W.C. Fields, Johnny Weissmuller and Gene Autry in the past to Jack Nicholson, Sylvester Stallone, Justin Timberlake, Adam Levine, George Lopez and Bruce Willis today.

The club was conveniently located around the corner from Universal Studios, allowing Dad to play early in the morning and, during summer months, late in the afternoon, often with Bob Hope.

Many days, Dad played a morning round and went to the racetrack in the afternoon. When asked by his playing partners if he wanted to go to the track with them, he invariably would answer, "I have a previous engagement, but I'll see you there." He then would arrive at the track accompanied by the caddies who had worked his foursome that morning. Inevitably, Dad would overpay each of them by $20 as seed money for their wagers.

"People ask me how much golf I've played and how I learned my golf," Dad said. "I learned it playing with these caddies, mostly, and watching pros play." Dad often went to the caddies' rooming house and rousted a few of them to play a $1 nassau. Norman Blackburn, in his book Lakeside Golf Club of Hollywood, 50th Anniversary Book, wrote that "Bing would rather win a buck from a caddie than a thousand from Dan Topping [the co-owner of the New York Yankees], which he did many times."

Dad was involved in a famous match with a notorious and mysterious Lakeside member. His name was LaVerne Moore, though he had taken the name John Montague, or Mysterious Montague, as he came to be known because of his clandestine nature. He was a very good golfer, purportedly one of the best in the country, according to legendary sportswriter Grantland Rice. Montague fell in with the Hollywood crowd, even living for a time with Oliver Hardy of Laurel and Hardy fame. One day, Montague defeated my father in a match at Lakeside. Afterward, in the clubhouse bar, my father complained that he hadn't been given enough strokes.

"I could beat you with a shovel, a bat and a rake," Montague replied.

"For how much?" Dad asked.

"For $5 a hole."

That was how it widely has been reported, but I've heard that the bet was for $5,000 a hole, a tidy sum among the well-heeled even today, but more so in those days.

They repaired to the first hole. Montague used a fungo bat off the tee and drove the ball into a bunker. From there, he took a shovel and scooped the ball onto the green about two feet from the hole. He made the putt by using the rake like a pool cue.

"I was history," Dad said.

The mystery surrounding Montague turned out to be the questionable past from which he was hiding. A story with photos on Montague, as his legend grew, appeared in Time magazine, piquing the interest of a law-enforcement official who had spent seven years working on a criminal case involving armed robbery and assault in upstate New York. Montague was arrested for the crimes, though later was acquitted of them.

Dad would arrive at the racetrack accompanied by the caddies who had worked his foursome that morning. Inevitably, he would overpay each of them by $20 as seed money for their wagers.

As for Dad's association with kings (or former kings), one was a golf partner, the Duke of Windsor, formerly King Edward VIII, who had abdicated his throne to marry an American socialite and divorcee, Wallis Simpson. On a visit to Paris one year, Dad teamed with a friend, Ray Graham, in a match with the Duke and Chris Dunphy, the chairman of the greens committee at Seminole Golf Club and one of Dad's friends. The Duke was notorious for his aversion to wagering any more than a few dollars. So neither Dunphy nor Dad bothered to tell him what the bet was that day. Yet every hole or two, either Dunphy or Dad would holler, "Texas!" Curious, the Duke asked Dunphy why they were always talking about Texas.

"Never mind," Dunphy said. "I'll explain later." He waited until the end of the round to tell him. "Every time Bing or I said 'Texas,' that meant we were doubling the bets."

"I say, Chris," the Duke replied, "I'm glad you didn't tell me about it at the time."

Dad mixed comfortably with England's royal family as well. In the summer of 1976, we spent a couple of weeks at Petworth House outside of London. During our stay there the entire royal family—Her Royal Highness Queen Elizabeth, Prince Charles, Prince Phillip and other notables—held a party with us, presumably to showcase their renowned houseguest. Meanwhile, Mom had instructed me to bow when I met the queen, but I thought she was kidding. Alas, I failed to make the gesture in a timely manner, resulting in a stern lecture in royal-family etiquette from my mother.

For my mom, being from West Columbia, Texas, meeting the royals and, better yet, spending time with them was a personal achievement. So a few weeks later when we were attending the races at the Goodwood Racecourse, Queen Elizabeth was there, too. Her Royal Highness sent an emissary down to invite us to the Royal Enclosure, or Royal Box, as Americans might call it. Mom was thrilled at the invitation, Dad less so. He repeatedly declined, citing the fact he was underdressed for the occasion. Top hat and tails generally are required for gentlemen in the Royal Enclosure, and Dad had a green plaid sports jacket that he wore far too often in his later years. The queen insisted that it didn't matter, but Dad continued to decline. In his defense, he was colorblind, and as I recall was wearing brown shoes with one red sock and one green sock. Mom, meanwhile, seethed at the missed opportunity.

Presidents were also playing partners of my father's, among them John F. Kennedy, with whom Dad played at Palm Beach Country Club in April 1961. "The president has a good-looking golf swing," my father said. "It's smooth. All the fundamentals are right. He has a good stance and grip and slow backswing. He hits the ball with determination. He's out there 240 or 250 yards." Dad partnered with the president in a match against Kennedy's father, Joseph, and Chris Dunphy.

One of the legendary stories included Dunphy failing to concede Kennedy's three-foot putt for par on the first hole, despite the president's plea to do so.

"Make a pass at it," Dunphy said. "I want to see your stroke."

"I work in the Oval Office all day for citizens like you," Kennedy replied. "And now you're not going to give me this putt?" Dunphy said nothing.

"OK," Kennedy said. "But let's keep moving. I've got an appointment after we finish with the director of the Internal Revenue."

"Putt's good," Dunphy said. "Pick it up."

Dad said the best part of Kennedy's game was how he would arrange matches on the first tee. "He'll only bet a dollar or two, but an awful lot of negotiation goes on before the clubs start swinging. He works out the best possible arrangement before he makes a move. It gives me confidence that he'll be able to handle those international rascals."

About those international rascals: After his abbreviated round with the president, Dad recounted the day to my mother. "He told me that during the round special agents came up to the president," Mom said. "They had a little conversation. Turns out that was the day of the kidnapping threat against Caroline." The president's daughter, 3 at the time, was staying at the nearby oceanfront home of her grandparents Joseph and Rose Kennedy and reportedly was the target of pro-Castro Cubans.

My father developed a friendship with President Kennedy, though he did not use his status to seek out these kinds of relationships. Basking in reflected glory was not part of his repertoire. These relationships always evolved through a mutual interest in golf. When President Kennedy was planning a weekend retreat in the Palm Springs area in 1962, he was invited to stay at Frank Sinatra's house in Rancho Mirage but chose to stay at my father's home instead. At the time, Kennedy's brother Robert F. Kennedy, the attorney general, was investigating organized crime figures, and the president balked at staying at the home of a man thought to have connections with those under investigation. Sinatra reportedly was livid. He had built a helicopter pad and a guest wing on the house for the occasion. And when he discovered the president would be staying at my father's house, he said, "Staying with Bing Crosby? He's not even a Democrat." A long-standing rumor, incidentally, was that Kennedy had a visitor during his stay at my father's house. Her name: Marilyn Monroe.

I was just turning 16 when Dad died in October 1977, leaving me with an emotional void. Dad's death at 74 was at the time considered a reasonably long life, yet it still came as a shock and was not easy for any of us. There isn't a road map for fatherless teens or, as I told my mother years later, for widows at 43.

Golf, meanwhile, continued to be the focal point of my youth, and the experiences I'd had at the Bing Crosby Pro-Am, handing out scorecards and pencils to the likes of Arnold Palmer, Jack Nicklaus, Lee Trevino and others, motivated me to work hard on my golf with the intention of playing the PGA Tour one day.

I fell short on that front, but I did win one very important tournament, the 1981 U.S. Amateur, less than four years after my father's death. I had been inspired by a cause greater than myself: I wanted to win to honor my father's memory.

Dad was a strong enough golfer to have played in the U.S. Amateur, in 1940, at Winged Foot. He also played in the British Amateur one year and countless other lesser amateur competitions. I had found a medal my father had received for participating in one of them, and I wore it on a chain around my neck throughout the 1981 Amateur, rubbing it for good luck in stressful situations. My mother, meanwhile, wore Dad's old sport coat and hat during the final match.

Dad was a remarkably humble man, and he expected the same of his kids. A reporter asked me what my father might have said had he been there to witness my victory. "Don't let it go to your head, son," I replied. Privately, I'm sure he would have had another reaction, one closer to that of his old road partner and golf foil, Bob Hope, 78 at the time, who was watching the telecast in the grillroom of a Minnesota golf club. When I holed the winning putt, I was told by an assistant professional at the club that Bob had cried. Hope's emotional reaction was a testament to his long and adoring friendship with my father and his understanding of what it would have meant to Dad had he been there.


Courtesy of Nathaniel Crosby

Nathaniel Crosby is the founder and president of Appletree Societies, providing affluent travel groups access to Appletree residences and private golf clubs and golf resorts in second-home and vacation-home markets around the country.