Natalie Oglesby Skalla: The Private Therapeutic Riding Instructor

Natalie Oglesby Skalla, the daughter of the legendary pop singer Frank Sinatra Jr., is a private and enigmatic individual. Born from Frank’s relationship with Mary Sue Oglesby, Natalie’s life has been closely connected to the music industry and its iconic figures. While her father, Frank Sinatra Jr., led a turbulent life under the shadow of his famous father, Natalie has chosen a different path, embracing a life away from the spotlight as a therapeutic riding instructor. In this article, we will delve into the life of Natalie Oglesby Skalla and explore her connection to the Sinatra legacy.

A Tumultuous Legacy

Frank Sinatra Jr.’s life was marked by both fame and hardship. Born on January 10, 1944, in New Jersey, United States, he grew up in the formidable shadow of his father, the iconic Frank Sinatra. Their relationship was complicated, strained by the pressures of living up to his father’s immense legacy and expectations.

At the age of 19, Frank Sinatra Jr. faced an unimaginable ordeal when he was kidnapped. However, his father, Frank Sinatra, came to his rescue, paying the ransom to secure his release. This harrowing event only intensified the complexities of their father-son relationship.

Embracing the Musical Journey

Despite the challenges he faced, Frank Sinatra Jr. was passionate about music, and in 1988, he took on the role of his father’s music director and conductor. This move allowed him to carve out his own identity in the music industry while still maintaining ties to the Sinatra legacy.

Frank Sinatra Jr. was married to Cynthia McMurrey, and together, they had a son named Michael Sinatra. Alongside his sisters, Nancy Sinatra, a successful pop singer and actress, and Tina Sinatra, who pursued a career as a television producer, the Sinatra family name remained prominent in the entertainment world.

A Daughter’s Private Path

Natalie Oglesby Skalla, the daughter of Frank Sinatra Jr. and Mary Sue Oglesby, opted for a different lifestyle altogether. Preferring privacy over public attention, Natalie has chosen to stay away from the limelight that often accompanies a famous last name.

Following her passion for helping others, Natalie pursued a career as a therapeutic riding instructor. This profession involves using horseback riding as a form of therapy to improve physical, emotional, and cognitive well-being for individuals with various conditions and challenges. By working with horses and their riders, Natalie has found fulfillment in making a positive impact on the lives of others.

Carrying the Sinatra Legacy

While Natalie Oglesby Skalla has chosen to lead a private life, she remains a living connection to the illustrious Sinatra legacy. Her grandfather, Frank Sinatra, was a legendary figure in the music industry, known for his captivating voice and enduring contributions to the world of entertainment. Her father, Frank Sinatra Jr., continued that legacy and made his own mark as a music director and conductor.

Frank Sinatra Jr.’s mother, Nancy Barbato, was also a significant figure in the music industry, standing by her husband’s side during his rise to stardom. Together, they formed a family that left an indelible impact on the world of music and beyond.


Natalie Oglesby Skalla’s story is one of quiet strength and resilience, choosing a path less traveled despite being born into a famous family. Her dedication to making a positive impact on others through therapeutic riding instruction reflects her compassionate nature and desire to help those in need. While she may have chosen to stay out of the public eye, Natalie’s connection to the Sinatra legacy remains an important part of her identity. As we remember the late Frank Sinatra Jr., we also acknowledge the life and choices of his daughter, Natalie Oglesby Skalla, as she continues to contribute to the world in her own unique and meaningful way.

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