The youngest son of Bing Crosby, Lindseay Crosby, was found dead in a small rented apartment in the Las Virgenes area of Calabasas, California, on December 11, 1989. The coroner pronounced him dead at 5:40 p. m. from a self-inflicted gunshot wound.
A rifle lay near his body. He was 51 years old. Family representatives said Lindseay had been crushed by the collapse of the inheritance trust he had relied on to sustain his life. He had been receiving treatment for alcoholism at a nearby facility and had reportedly planned to return to his family afterward.
Lindseay was the youngest of the four sons from Bing Crosby’s first marriage to Dixie Lee. Their story stands in stark contrast to the warm, effortless image of the man who recorded “White Christmas” and became one of the most beloved entertainers in American history. Bing Crosby rose from modest beginnings in Spokane, Washington, to become a foundational figure in American entertainment. He won an Academy Award for “Going My Way,” and his recording of “White Christmas” remains the best-selling single in music history.
In the 1940s, public opinion polls ranked him among the most admired men alive, ahead of presidents and the Pope. By the time he married Dixie Lee in 1930, she was the more established performer. But as Bing’s career exploded, Dixie retreated from public life and sank into alcoholism. Their household became defined by Bing’s rigid control and Dixie’s instability.
Gary Crosby, born in 1933, was the eldest. Twins Dennis and Philip were born in 1934, and Lindseay arrived in 1938. In his 1983 memoir “Going My Own Way,” Gary alleged that Bing administered ritualized beatings with a metal-studded belt. He described a home governed by fear and emotional coldness, where punishment was designed to shame rather than correct.
Philip publicly defended his father, insisting the discipline was earned and proportional. Dennis confirmed Gary had been treated the most severely. Dixie Lee Crosby died of ovarian cancer on November 1, 1952. She was 42.
Gary was 19, the twins were 18, and Lindseay was 14. By all accounts, Bing did not draw closer to his grieving sons. The family continued operating as it always had. Five years later, Bing remarried.
Katherine Grant was 23, sober, and organized. They had three children: Harry in 1958, Mary in 1959, and Nathaniel in 1961. Bing moved the new family to Hillsborough in Northern California, deliberately raising them away from Hollywood. The second family described a very different father.
Harry called the move a “reset button. ” Mary remembered a father who was present, playful, and warm. The children of the second marriage spoke of meals together, laughter, and a man who seemed to understand that presence mattered more than discipline. For the four sons of the first marriage, this contrast became evidence that their father had always been capable of tenderness—just not for them.
The first four sons struggled through adulthood. They formed a nightclub act called the Crosby Boys, which collapsed under their drinking and instability. Bing himself once had to step in and perform as the fourth brother when Gary was too drunk to go on. Bing Crosby died on October 14, 1977, on a golf course outside Madrid, of a massive heart attack.
He was 74. For his first four sons, his death closed any possibility of a reckoning or a private apology. In 1983, Gary’s memoir tore open the family myth. Gary detailed the beatings and the emotional coldness of his childhood.
The family split publicly. Lindseay welcomed the book. Philip called Gary a “crybaby. ” Katherine published “My Life with Bing” the same year, presenting a gentler portrait of her husband.
The two accounts were never reconciled. When Lindseay died in December 1989, the loss of the trust income from his mother’s estate was cited as the immediate cause of his despair. His death made Gary’s memoir of the previous decade look prophetic rather than bitter. Seventeen months later, on May 4, 1991, Dennis Crosby was found dead in his home in Novato, California.
The cause was an apparently self-inflicted shotgun wound. He was 56. A roommate discovered the body. The coroner ruled it a suicide.
Mary Crosby later offered the most blunt family verdict: “Two out of four commit suicide. Something is very wrong with the picture. ”
Gary Crosby died of lung cancer in Burbank on August 24, 1995. He was 62.
He had lived long enough to see two of his brothers take their own lives, validating what he had written, though it did not heal the family. Philip Crosby, the last surviving son of the first marriage, died on January 13, 2004. He was 69. He had spent his adult life defending his father’s memory, insisting the household had been normal, while struggling with the same alcoholism that defined his brothers.
All four sons of Bing and Dixie Crosby died before turning 70. Two died by suicide, one of cancer, and one at 69 leaving no public recantation of his support for his father. The legal battles continued after the sons died. In 1996, the trust under Dixie’s name sued HLC Properties Limited and Katherine Crosby over income derived from community property of the marriage.
The case was settled in 1999 for approximately $1. 5 million, but further proceedings continued into the 2000s over the commercial value of Bing’s publicity rights. The second family survived. Harry Crosby built a career in investment banking, deliberately separating himself from the entertainment industry.
Mary Crosby remains known for her role on “Dallas. ” Nathaniel Crosby won the U. S. Amateur Championship in 1981, carrying on the sport his father loved.
Katherine Crosby died in September 2024 at the age of 90, having outlived all four of Bing’s first sons by decades. The Hillsborough estate that symbolized the second family’s fresh start was sold in 2025. The contrasting fates of the two families remain permanently unresolved. The first family produced four sons, all of whom died young, two by their own hands.
The second family produced three children who survived and spoke of their father with affection. Both descriptions of Bing Crosby appear to be true. He was a man who lived as two different fathers in two different households, and the first four sons bore the cost of the earlier version.