Complicated Love Life of Frank Sinatra's Son - From Love Affairs to Not Acknowledged Children

Frank Sinatra's son had a very complicated love life. He had four kids with women all named Mary before he died, but only one was acknowledged in his will and obituary. 

Frank Sinatra left a long-lasting legacy when he passed away, after which one of his kids, Frank Sinatra Jr, took up the baton. Frank Jr enjoyed fame like his father, and he was also popular among the ladies.

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

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 eventually found out, and he did give him hell for it. Here are the juicy details about the life he lived. 

FRANK SR CAUGHT WIND OF HIS FIRST CHILD

Frank Jr had a very complicated love life. The first woman he had a child with was Mary Wallner. Their daughter, Francine, was born towards the end of his four-year affair with Mary Wallner in 1972. Frank Jr paid child support but wanted nothing to do with Francine.

He also refused to publicly acknowledge her as his child, which irked Wallner so much that she decided to let his father know. It was reportedly the first time Frank Sr heard about his grandchild, and according to Wallner, it made Frank Jr very angry. 

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

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

LAWSUIT FROM HIS SECOND LOVER

The second child the talented Frank Jr had was with a woman named Mary Sue Oglesby. She had his second daughter Natalie, but as with Wallner, he refused to acknowledge her as his. 

Oglesby was fine with that, but in 1995 when her daughter clocked 17, she filed court documents to petition for child support. 

Till today, some believe it was all a stunt to make Frank Jr more popular.

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. 

According to Oglesby, who succumbed to cancer in 2011, Frank Jr paid a total of $1,500 in pregnancy-related medical bills but was a no show on the delivery day. 

The next month, he flew them both to Wichita, Kansas, to see his daughter for the first time. Despite that, he refused to provide support, and Oglesby did not mind until it was time for her daughter to attend college. 

According to those close to the family, Frank Jr only agreed to fund Natalie's college fees for Mary dropping the lawsuit, which she did because she wanted nothing more from him. 

PROPOSED TO HIS THIRD MISTRESS

Mary Fleming conceived Frank Jr's third love child. Before she welcomed their son, she had no idea he already had two children out of wedlock, one of whom was born just months before her delivery. 

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

After Francis was born, Frank Jr dropped out of Fleming's life and began an affair with his secretary Patricia Ward. According to Mary, he always lived in fear of his father — a behavior motivated by greed. 

Fleming later revealed that she and the singer kept communicating after their son was born even though he wanted nothing to do with him. She said he was afraid of what his family would think, so he tried to hide her when he learned of her pregnancy. 

Later, he asked her if she wanted to marry him, but because she felt the proposal was half-hearted, she refused, wanting to give it more time. It was a decision Fleming came to regret as she believed Frank Jr would have acknowledged her son as his had they married. 

Frank Jr visited his son just once before he totally turned his back on him. He paid child support but avoided any relationship with Francis even when the boy deliberately sought him out. 

HE WAS MARRIED BRIEFLY 

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

Fleming believes that their child was only acknowledged because Ward knew too much about Frank Jr, and his father had warned him to do right by her. 

The only woman Frank Jr ever married was Cynthia McMurrey, the family lawyer. He married her five months after his father's death in 1998 at age 82. 

The marriage lasted just over a year, but the two remained close until his demise. 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. 

HIS DEATH 

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

Despite his tumultuous love life, Frank Jr was loved by all. He had an unhealthy relationship with his father for most of his life, always gone on tours. 

According to Fleming, who befriended the kidnapping mastermind, Barry Keenan, later after his release, the reason for the kidnap was to bring Frank Jr closer to his father. 

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

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

Together with two other men, 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.

All three men were later caught but only ended up serving minimal sentences. Till today, some believe it was all a stunt to make Frank Jr more popular.

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