Home Poal9

The Two Families Of Bing Crosby: Inside The $40 Million Estate Sale And The Tragic, Triumphant Lives Of His Seven Children

• minute read
Contents

The legacy of Harry Lillis "Bing" Crosby Jr., the iconic crooner whose voice is synonymous with the holidays, is far more complex than the cheerful image he projected on screen. As of late 2025, the Crosby family name is back in the news, not for a new song, but for the final dissolution of a major part of his estate, a move prompted by the recent passing of his second wife. The story of Bing Crosby’s family is one of immense fame and wealth intertwined with deep-seated tragedy, controversy, and, for his surviving children, a quiet determination to forge their own paths.

The legendary singer, known as "Der Bingle," was married twice and fathered seven children across two distinct generations, creating two very different family narratives. The recent death of his widow, Kathryn Grant Crosby, in September 2024, has brought a flurry of activity, including the sale of the family's iconic Hillsborough, California, estate for a staggering $40 million, marking a definitive new chapter for the Crosby heirs. This deep dive explores the full, often-challenging, history of the Crosby family and the current status of its surviving members.

The Complete Family Profile: Bing Crosby's Wives and Seven Children

Bing Crosby’s family life was split into two eras, defined by his two marriages. The first was marked by a shared struggle with alcoholism and a public-private duality that resulted in immense pain for his four eldest sons. The second, with a much younger wife, was characterized by a more stable, though still famous, upbringing for his three youngest children.

  • Full Name: Harry Lillis "Bing" Crosby Jr.
  • Born: May 3, 1903 (Tacoma, Washington)
  • Died: October 14, 1977 (Madrid, Spain)
  • First Wife: Dixie Lee (Actress, Singer) (m. 1930; d. 1952)
  • Children with Dixie Lee (The Four Sons/The Crosby Boys):
    • Gary Crosby (1933–1995): Singer, Actor, Author (*Going My Own Way*).
    • Dennis Crosby (1934–1991): Singer, Actor.
    • Phillip Crosby (1934–2004): Singer, Actor.
    • Lindsay Crosby (1938–1989): Actor, Singer.
  • Second Wife: Kathryn Grant Crosby (Actress, Singer) (m. 1957; d. September 20, 2024)
  • Children with Kathryn Grant:
    • Harry Lillis Crosby III (b. 1958): Investment Banker, former Actor.
    • Mary Frances Crosby (b. 1959): Actress (known for *Dallas*).
    • Nathaniel Patrick Crosby (b. 1961): Professional Golfer, Golf Executive.
  • Key Films/Songs: *White Christmas*, *Going My Way* (Oscar win), *High Society*, "Pennies from Heaven."

The Darker Side of the Legacy: The Tragedy of The Crosby Boys

The four sons from Bing Crosby's first marriage with Dixie Lee—Gary, Dennis, Phillip, and Lindsay—were collectively known as "The Crosby Boys" and attempted to follow their father into show business. Their lives, however, were tragically marked by addiction, mental health struggles, and early deaths.

The Shocking Memoir: *Going My Own Way*

The public perception of Bing Crosby as the jovial, easygoing crooner was shattered in 1983 when his eldest son, Gary Crosby, published his tell-all memoir, *Going My Own Way*. Gary detailed a childhood marred by alleged emotional cruelty, harsh discipline, and physical abuse at the hands of his father.

The book described Bing as a cold, remote, and often sadistic parent who used corporal punishment, including a studded belt, to enforce discipline. The revelations were met with mixed reactions; while some family members, including Phillip and Dennis, initially corroborated the accounts, others, notably the children from the second marriage, staunchly defended their father’s memory.

The memoir remains a pivotal, controversial entity in the Crosby family history, forcing a re-evaluation of the American icon's private life. All four sons from this first marriage struggled with alcoholism and died prematurely. Tragically, both Dennis and Lindsay Crosby died by suicide.

The Second Family and the Recent Estate Sales (2024-2025)

Following Dixie Lee's death from ovarian cancer in 1952, Bing Crosby married actress Kathryn Grant (known as Olive Kathryn Grandstaff) in 1957. Grant was 30 years his junior and gave birth to his three youngest children: Harry, Mary, and Nathaniel. This second family enjoyed a different dynamic, as Bing was older, less driven by his career's demands, and reportedly a gentler, more involved father.

The recent death of Kathryn Grant Crosby on September 20, 2024, at the age of 90, marked the end of an era for the family and triggered the sale of significant assets.

The $40 Million Hillsborough Home and Fabergé Auction

In the wake of Kathryn's passing, the family put their sprawling, iconic Bay Area home in Hillsborough, California, on the market. The property, where the second family lived for decades, was listed with a reported asking price of $40 million. This sale represents the final major liquidation of the family's core properties, solidifying the transition of the Crosby estate to the next generation.

Additionally, a significant auction of personal treasures collected by Bing and Kathryn, including Fabergé items, cowboy paintings, and European furniture, recently brought in $6.7 million. These sales highlight the immense and tangible value of the Crosby legacy beyond just his music.

The Surviving Heirs: Careers and Current Lives of the Youngest Crosbys

Unlike their older half-brothers, the three children from Bing and Kathryn’s marriage have found successful and relatively stable careers, largely outside the direct shadow of their father’s musical fame, though all have spent time in the entertainment industry.

Mary Crosby: The Iconic Soap Villain

Mary Frances Crosby is arguably the most famous of the second generation, carving out a successful career as an actress. She is best known for her iconic role as Kristin Shepard, the woman who shot J.R. Ewing in the legendary 1980 "Who Shot J.R.?" episode of the television series *Dallas*. Her work in this major cultural entity secured her own place in television history.

Harry Crosby: From Screen to Investment Banking

Harry Lillis Crosby III initially followed his parents into acting, appearing in films like *Friday the 13th* (1980). However, he eventually transitioned to a highly successful career in finance. He now works as a prominent investment banker, a stark departure from the family's entertainment roots. Harry has also been instrumental in managing his father's estate, including the recent decision to sell a stake to boost the continued promotion of Bing’s work.

Nathaniel Crosby: The Golfing Champion and Executive

Nathaniel Patrick Crosby found his passion in golf, a sport his father loved and helped popularize through the Bing Crosby National Pro-Am tournament (now the AT&T Pebble Beach Pro-Am). Nathaniel won the prestigious 1981 U.S. Amateur and went on to a professional career. More recently, he has served in leadership roles in the sport, including captaining the victorious U.S.A. Walker Cup team in 2019, cementing his own athletic legacy. He credits the game with strengthening his bond with his famous father.

The enduring appeal of Bing Crosby, especially during the holiday season with his record-breaking hit "White Christmas," ensures that the family name will remain a relevant cultural entity. The recent estate sales and the passing of Kathryn Grant Crosby serve as a poignant reminder that while the golden age of Hollywood is long past, the complex and multifaceted legacy of one of its biggest stars continues to unfold through the lives of his surviving children.

bing crosby and family
bing crosby and family

Detail Author:

  • Name : Trevion Kuhn
  • Username : mauricio.kozey
  • Email : ned.ortiz@considine.com
  • Birthdate : 1980-05-23
  • Address : 47512 Hammes Path Suite 640 Christaberg, CT 52240-4332
  • Phone : (802) 992-0532
  • Company : Bode-Hill
  • Job : Automotive Glass Installers
  • Bio : Qui et nihil earum ut. Illo cupiditate eum maxime molestiae. Esse veritatis nam ut voluptatem. Voluptatem sit aspernatur sequi deleniti aut.

Socials

linkedin:

instagram:

  • url : https://instagram.com/loyeffertz
  • username : loyeffertz
  • bio : Aspernatur labore veniam aut eum sunt. Cumque voluptatem aut sint.
  • followers : 1401
  • following : 2980

facebook:

twitter:

  • url : https://twitter.com/loy_dev
  • username : loy_dev
  • bio : Aliquam voluptas voluptas aspernatur optio et. Id commodi et beatae aut provident ab laboriosam dicta. Et animi dolor corrupti ex autem culpa.
  • followers : 3727
  • following : 957

tiktok:

  • url : https://tiktok.com/@effertzl
  • username : effertzl
  • bio : Dolorem dolorem quis omnis consequuntur ducimus.
  • followers : 1799
  • following : 704

Random Posts