Challenges in the Life of Frank Sinatra in a Detailed Timeline

A closer look at the defining struggles that shaped Frank Sinatra's life and career.

Frank Sinatra, nicknamed "Chairman of the Board" and "Ol' Blue Eyes", was a highly popular and influential American singer and actor of the 20th century. He is considered one of the best-selling music artists globally, with estimated record sales of 150 million. Sinatra's impact on music and entertainment remains significant.

Sections (6)

Full Timeline Early Life & Education Career & Achievements Success & Recognition Challenges & Struggles Legacy & Impact

November 1945: Involvement in Froebel High School strike

In November 1945, Frank Sinatra was invited to Gary, Indiana, to try to settle a strike at Froebel High School regarding racial policies, leading to accusations of being a communist.

1946: Attendance at the Mafia Havana Conference

In 1946, Frank Sinatra attended the Mafia Havana Conference with Lucky Luciano, resulting in negative press with headlines like "Shame, Sinatra".

1947: Fight with Lee Mortimer

In 1947, Frank Sinatra received negative press for a fight with Lee Mortimer.

1950: Fight with photographer Eddie Schisser

In 1950, Frank Sinatra had a violent incident with photographer Eddie Schisser in Houston, leading to negative press.

1954: Fight with Judy Garland's publicist Jim Byron

In 1954, Frank Sinatra was involved in a fight with Judy Garland's publicist, Jim Byron, on the Sunset Strip, contributing to negative press.

1962: Snub by John F. Kennedy

In 1962, Frank Sinatra was snubbed by President John F. Kennedy, who stayed with Bing Crosby instead of Sinatra in Palm Springs due to FBI concerns.

1963: Suspension of gambling license and relinquishing of casino shares

In 1963, Frank Sinatra's gambling license was temporarily suspended after Giancana was spotted at the Cal Neva Lodge & Casino, leading him to give up his shares in Cal Neva and the Sands.

1970: Release of Watertown

In 1970, Frank Sinatra released "Watertown", a critically acclaimed concept album, though it was not commercially successful.

1973: Confrontation with Maxine Cheshire

In 1973, Frank Sinatra confronted Washington Post journalist Maxine Cheshire, making offensive remarks and receiving negative press.

January 1977: Death of Dolly Sinatra and Royal Albert Hall Performance

In January 1977, Frank Sinatra's mother, Dolly, died in a plane crash while traveling to see him. He canceled shows and spent time in Barbados. In March 1977, he performed at the Royal Albert Hall in London, raising money for charity.

1978: Lawsuit Against Land Developer

In 1978, Frank Sinatra filed a $1 million lawsuit against a land developer for using his name in the "Frank Sinatra Drive Center" in West Los Angeles.

September 21, 1983: Lawsuit Against Kitty Kelley

On September 21, 1983, Frank Sinatra filed a $2 million court case against Kitty Kelley before her unofficial biography, 'His Way', was published.

September 19, 1984: Dropped case against Kitty Kelley

On September 19, 1984, Frank Sinatra was forced to drop his case against Kitty Kelley, with several leading newspapers expressing concerns about censorship.

1986: Collapse on Stage and Rat Pack Reunion Tour

In 1986, Frank Sinatra collapsed on stage in Atlantic City and was hospitalized for diverticulitis. Two years later, he reunited with Martin and Davis for the Rat Pack Reunion Tour.