According to a new book, Frank Sinatra grappled with unending guilt over leaving his first wife and three children, yearning for reconciliation until his final days.

Tony Oppedisano, Sinatra’s former manager, reveals in “Sinatra and Me: In the Wee Small Hours” that the iconic singer struggled to completely move on from the dream of his original Italian family.

Despite his deepest desire to mend things with Nancy Sinatra, his lack of impulse control around women led him down a path of three more marriages and numerous affairs.

The marriage with Mia Farrow, nearly 30 years his junior, was an attempt at rejuvenation but faltered as she resisted a traditional homemaker role.

Similarly, his relationship with Ava Gardner crumbled due to her overshadowing success and his perceived emasculation.

Oppedisano recounts Gardner’s scathing remark about Farrow being a ‘boy with a c***,’ highlighting Sinatra’s attraction to unconventional traits.

While Sinatra’s fourth marriage to Barbara Marx initially seemed promising, it soured after a tragic incident strained their bond.

Despite Barbara’s beauty, underlying insecurities plagued their union.

Surprisingly, Sinatra refrained from a physical relationship with Marilyn Monroe, feeling a sense of protection towards her given her troubled past.

“Sinatra and Me: In the Wee Small Hours” sheds light on the crooner’s early struggles, including a birth that nearly claimed his life, resulting in lasting brain damage affecting his emotional stability.

His insatiable drive for success stemmed from a tumultuous relationship with his father and his relentless pursuit of proving him wrong.

Oppedisano delves into Sinatra’s complex persona, revealing his loose s**ual morals and penchant for unconventional relationships.

Despite his infidelities, Nancy Sinatra maintained a steadfast loyalty, viewing him as a flawed but devoted father figure.

Sinatra’s turbulent marriages, marked by fiery passion and intense conflicts, ultimately led to multiple divorces and heartache.

The book also explores Sinatra’s platonic yet intriguing friendship with Jackie Kennedy, showcasing an undeniable chemistry between them.

Contrary to rumors, Sinatra’s alleged affair with Natalie Wood at age 40 was debunked by Wood’s former husband, Robert Wagner.

Additionally, Sinatra’s brief encounter with Donald Trump ended on a sour note, emphasizing their incompatible personalities.

In recounting Sinatra’s intimate connections with Hollywood legends like Monroe and Kennedy, Oppedisano paints a vivid portrait of a man torn between his public persona and private struggles.

Sinatra’s legacy is one of unmatched talent marred by personal demons and unfulfilled yearnings.

As “Sinatra and Me: In the Wee Small Hours” hits shelves, readers are invited to explore the multifaceted life of a music icon whose complexities continue to captivate audiences worldwide.