The Complicated Love Life of Frank Sinatra’s Son


Frank Sinatra’s son had a very complicated love life. He had four kids before he died, but only one was acknowledged on his will and obituary, and all his baby mamas are named Mary. 

Frank Sinatra Jr. took over the reins after his death. Frank Jr was a celebrity just like his father and was popular with women.

He reportedly had four kids from his love affairs with four different women — three of whom were named Mary — but while his father lived, Frank Jr tried very hard to keep knowledge of his love affairs from him.

Picture of Frank Sinatra Jr. with his father Frank Sinatra | Photo: Getty Images

He was afraid that if his father discovered them, he would be left destitute. Frank Sr. found out and did not mince words. Here are some details about his life.


Frank Jr had a very complicated love life. Mary Wallner was the first woman with whom he had a baby. Francine, their daughter, was born in 1972 after a four-year affair between Mary Wallner and Frank Jr.

Frank Jr. paid child maintenance but refused to have anything to do with Francine. Wallner became so upset by Frank Jr’s refusal to acknowledge Francine as his child that Wallner decided to tell his father. Wallner claims that this was Frank Jr’s first encounter with his grandchild.

Frank Sinatra, his wife and children, Nancy and Frankie, Jr, having dinner in the Cub room at Sherman Billingsley's Stork Club, dispelling any rumors of a breakup with his wife on October 17, 1947 | Photo: Getty Images


The second child the talented Frank Jr had was with a woman named Mary Sue Oglesby. He refused to recognize Natalie as his second child, as he did with Wallner.

Oglesby was okay with this, but when her daughter turned 17 in 1995, she filed court papers to petition for child support.

Many believe that Frank Jr was just trying to get Oglesby more attention.

Oglesby, who worked as the manager of an apartment complex in Tulsa, Oklahoma, told the court that her affair with Frank Jr lasted years, and whenever they linked up for trysts while he worked, he would often use the name “Mrs. Sinatra.”

According to court documents Oglesby submitted, “Natalie was deliberately conceived by Sinatra and Ms. Oglesby in Room 147 of the Holiday Inn at Chicago’s O’Hare Airport in November 1976.”

Perhaps that was what motivated her to keep the room receipt on which she scribbled, “The weekend we made Natalie.” She attached it and a receipt for her plane ticket to the court documents she filed.

Oglesby said that Frank Jr, who died from cancer in 2011, paid $1,500 in pregnancy-related medical expenses but was absent on the day of her delivery.

He flew them both to Wichita in Kansas the next month to meet his daughter. Oglesby was not happy until her daughter went to college, but he refused to pay support.

According to close family members, Frank Jr. agreed to pay Natalie her college fees for Mary dropping the suit. Mary dropped the lawsuit because she wanted nothing else from him.


Mary Fleming conceived Frank Jr’s third love child. She didn’t know that Frank Jr had already had two children from his previous marriage, the second of which was born months before she gave birth to their son.

Frank Jr reportedly insisted that their son be named after him, but as he did with Oglesby, the singer was absent during the delivery of his son Francis Wayne Sinatra Jr in May 1978 — he blamed this on threats he received from his father.

“When his father found out I was pregnant, he [Frank Sinatra] called him to his house in Palm Springs, kept him there for two days, and gave him hell,” Fleming said.

Frank Jr. was born shortly after Francis. He began an affair, according to his secretary Patricia Ward. According to Mary, he always lived in fear of his father — a behavior motivated by greed.

Fleming later revealed to Mary that she kept in touch with the singer after their son was born, even though Fleming didn’t want anything to do. He tried to conceal that he was pregnant because he was worried about what his family might think.

He later asked her if they wanted to be married. But she declined because she felt the proposal wasn’t serious enough. Fleming regretted this decision as she believed Frank Jr. would have recognized her son as her husband had they been married.

Frank Jr. visited his son once before turning his back completely on him. He did not pay child support and avoided any relationship with Francis, even when he was genuinely interested in him.


The only child Frank Jr acknowledged in his lifetime was Michael Francis, the son he conceived with his secretary Patricia Ward.

Fleming believes Ward did not acknowledge their child because Ward knew too much, and Ward had warned him to be fair with her.

Frank Jr. married Cynthia McMurrey, a family lawyer. Five months after his father’s death, Frank Jr married her at the age of 82.

They were close for nearly a year before he died. His only acknowledged son, Michael, was expected to receive the bulk of his estate, but his other grandkids would later get engaged in a feud over his property.


Frank Jr died of a heart attack at age 72 while on tour in Daytona Beach, Florida. His surviving family cited the cause of death as cardiac arrest.

Frank Jr. loved everyone, despite his complicated love life. He had an unhealthy relationship with his father for most of his life, always away on tours.

Fleming, who later became friends with Barry Keenan (the kidnapping mastermind), said that Frank Jr. was kidnapped to bring his father closer.

Frank Sinatra, Jr. performs at Hard Rock Live! in the Seminole Hard Rock Hotel & Casino on March 3, 2011 | Photo: Getty Images

Keenan successfully kidnapped Frank Jr, who was allegedly talked into cooperating with them to avoid gunfights with the police. Frank Sr paid a ransom of $240,000, and his son was released two days later.

The men were all later captured but served only minimal sentences. Some believe that it was a publicity stunt to make Frank Jr. more famous.

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