Natalie Oglesby Skalla: Inside the Life of Frank Sinatra Jr.’s Daughter

Natalie Oglesby Skalla is the second daughter of Frank Sinatra Jr., the late American songwriter, actor, conductor, and singer. She was born in 1977 as a result of her father’s relationship with Mary Sue Oglesby.

Sinatra Jr. was known for having many relationships that produced many children. Despite gaining fame, he had a strained relationship with his daughter and two of his other children, as they were never close before his death. Here’s all about Farank Sinatra Jr.’s daughter, who is a therapeutic riding instructor.

Natalie Oglesby Skalla’s Biography Summary

  • Full name: Natalie Oglesby Skalla
  • Nickname: Natalie
  • Gender: Female
  • Date of birth: 1977
  • Natalie Oglesby Skalla’s Age: 47 years old
  • Ethnicity: White
  • Nationality: America
  • Sexual Orientation: Straight
  • Marital Status: Married
  • Natalie Oglesby Skalla’s Husband: Brian Skalla
  • Natalie Oglesby Skalla’s Parents: Frank Sinatra Jr. (father) and Mary Sue Oglesby (mother)
  • Siblings: (Half-siblings: Francine Sinatra Anderson, Francis Wayne Sinatra, and Michael Sinatra)
  • Famous for: Being the daughter of the late singer Frank Sinatra Jr.
  • Natalie Oglesby Skalla’s Instagram: @nataliehazardskalla

Natalie Oglesby Skalla was Born in 1977

As much as Natalie Oglesby Skalla’s date and month of birth are unknown, she was born in 1977 in the United States of America. The 47 year-old daughter of the singer was named after her great-grandmother, Natalie Della Garaventa. The riding instructor is of white ethnicity and holds American citizenship. She was born to Frank Sinatra Jr. and Mary Sue Oglesby.

Natalie Oglesby Skalla has three other half-siblings from her father’s relationships, and they are Francine Sinatra Anderson, Francis Wayne Sinatra, and Michael Sinatra. Natalie only rose to the spotlight for being the daughter of the musician cum actor, and as such, details of her early, mid, and higher education are unknown.

Natalie Oglesby Skalla’s Parents Were Never Married


The Hollywood actor Frank Sinatra Jr. was never married to Natalie Oglesby Skalla’s mother, Mary Sue Oglesby. The duo were in a long-term relationship that lasted for several years. According to her, he flew her around the country, addressing her with the title of Mrs. Sinatra for trysts.

Six months after the birth of his daughter, their relationship abruptly came to an end, and he was faced with lots of court petitions from her. Frank also severed ties with his daughter and didn’t regard her as his child.

Natalie Oglesby Skalla’s Relationship With Her Father was Strained From Birth

Despite planning the birth of Natalie Oglesby Skalla with her mother, Frank Sinatra Jr. turned out to ignore his daughter. Though he paid the pregnancy-related bills, which were about $1,500, one would think that he accepted his daughter wholeheartedly. The actor was not there at the time of her birth but instead flew Mary and her newborn child to Wichita, Kansas, to see his daughter for the first time.

After some time, he withdrew himself from the picture, stating that he would be giving child support. Just like her other half-siblings, Francine Sinatra Anderson and Francis Wayne Sinatra, Natalie wasn’t left out in the neglect of their father. For reasons best known to him, Francis Sinatra Jr. refused to stand as a father figure.

As such, Natalie Oglesby Skalla grew up knowing that she was not acknowledged by her father as his biological daughter, nor did he provide financial support from her early years to high school. The actor only started contributing to her education while she was in college. Despite her strained relationship with her father, she spent her days growing up happily under the care of her mother.

Natalie Oglesby Skalla, like every other child, didn’t get to meet her father nor share the love and bond between a father and a daughter. Though it was not all that rosy for her, knowing that her father chose not to regard her as his daughter, she still faced life with bravery, giving all her love to her mother.

Who is Natalie Oglesby Skalla’s Mother

Mary Sue Oglesby is one of the numerous women that Frank Sinatra dated. Together with the actor, they had Natalie after a long relationship. Mary was born on December 26, 1947, in Tulsa, Tulsa County, Oklahoma, USA. She is of white descent and holds American citizenship.

When Frank Sinatra neglected her and her daughter, she sued him in court for child education, maintenance, and support. Reports have it that she stated in the court documents that she had her daughter’s birth planned with the actor. She further stated that her daughter was conceived in Room 147 of Holiday Inn at Chicago’s O’Hare Airport in 1976.

Mary provided the hotel receipt in court, with a short sentence by the side that read “The Weekend we made Natalie.” The plane ticket bill was also attached as evidence. The actor struck a deal with her to drop the charges in exchange for Natalie Oglesby Skalla’s college fees. After a long battle with cancer, she died on February 23, 2011.

Natalie Oglesby Skalla is a Therapeutic Riding Instructor

Despite being neglected by her father, Natalie Oglesby Skalla still grew up to become a dignified woman. The career path that she has chosen is unknown as she has not made it known to the public. However, according to sources, she was addressed in a post by Equine Empowerment in 2019 as Frank Sinatra’s daughter, who is a therapeutic riding instructor.

The post was created to congratulate her on completing PATH International Instructor Certification and to recognize her hard work on the job. It also included her level in rodeo and riding. According to a source, she is an upcoming actress, but the movies that she has featured in are unknown.

It has been impossible to peg her net worth as she has not revealed much about it. But it is seen that she earns from her known career. With a father that has made a fortune for himself and has a net worth that is estimated at $50 million, many would think that Natalie should be extremely rich. It is not so, as she was excluded alongside her other two half-siblings, Francine Sinatra Anderson and Francis Wayne Sinatra. Her father left all his money and properties to his last son Michael Sinatra.

Meet Natalie Oglesby Skalla’s 3 Half-Siblings 

Natalie Oglesby Skalla has three half-siblings born to her father by three other different women. Below is a glimpse into her half-siblings:

Anderson, Francine Sinatra 

  • Date of birth: November 16, 1972
  • Age: 51 years old

Natalie Oglesby Skalla

Francine Sinatra Anderson is the actor’s first daughter, whom he had with Mary Wallner, born on November 16, 1972. Her mother was in a four-year relationship with Frank Sinatra Jr. when she conceived and gave birth to their daughter. Just like his other two kids, the actor neglected and rejected her, but her mother’s resilience gave her a place in the Sinatra family.

Francis Wayne Sinatra

  • Date of birth: May 8, 1978
  • Age: 46 years old

Francis Wayne Sinatra is the first son of Frank Sinatra, born to him by Mary Fleming. Despite his position as the first son and taking after his father’s name, he was still not recognized as a member of the Sinatra family by his father. As such, he was not included in his father’s will.

Michael Sinatra

  • Date of birth: March 1, 1987
  • Age: 37 years old

Natalie Oglesby Skalla

Michael Sinatra is the last child and second son of Frank Sinatra Jr., born to him by his secretary and mistress, Patricia Wards. He is the only child of the actor who was recognized and treated as a biological child. Michael was the only one that inherited his father’s $50 million estate.

Who Is Natalie Oglesby Skalla Married To?

Natalie Oglesby Skalla is married to Brian Skalla. Details about how they met, when they got married, and how long they have lived together have been kept under the radar. It is also not known if she has any children with her husband, as she is seen to live a low-profile life.


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