Frank Sinatra and Sammy Davis Jr.are two of the most iconic figures in American entertainment history.

Their relationship, spanning over five decades, was marked by groundbreaking moments, deep loyalty, racial tensions, and the complicated dynamics of friendship and power within the racially segregated America of the mid-20th century.

Though rumors and gossip swirled around their bond, Sinatra’s final words about Davis offered a profound affirmation of their connection — one rooted in respect and true friendship.

 

The story of their friendship began in 1941 backstage at the Michigan Theater in Detroit.

Frank Sinatra, then a rising star and lead singer of the Tommy Dorsey Orchestra, met a young 16-year-old Sammy Davis Jr., who was performing with the Will Mastin Trio, a little-known Black vaudeville group.

Their first conversation happened casually over a shared sandwich during intermission, but it was the start of a bond that would shape both their lives.

 

Davis, from a young age, admired Sinatra not just for his fame but for what he represented: stage power, the right to speak, and the right to be respected — privileges Black artists were often denied in a racially divided America.

Sinatra’s willingness to sit down and connect with Davis during an era of strict segregation was unusual and meaningful.

 

Throughout the 1940s and 1950s, Sinatra quietly but significantly supported Davis’s career.

When Davis was drafted into the army in 1944, he faced brutal racism but used his talent to entertain soldiers and fight prejudice.

Sinatra’s anti-racist stance was evident in his participation in the short film *The House I Live In*, which condemned racial prejudice and won an honorary Oscar.

For Davis, this was a personal message of hope.

 

Sinatra’s influence helped Davis break through racial barriers.

For example, in 1947, when Sinatra performed at the prestigious Capital Theater in New York, he insisted that the Will Mastin Trio open for him, demanding a fee five times higher than usual to ensure the group’s acceptance by a predominantly white audience.

This exposure was critical in elevating Davis’s career.

 

Their relationship deepened beyond professional support. When Davis suffered a severe car accident in 1954 that cost him his left eye, Sinatra paid his medical bills and personally cared for him during his recovery.

It was Sinatra who convinced the depressed Davis to keep fighting, offering a home and friendship when Davis felt he had nowhere else to go.

 

Las Vegas in the 1950s was a hub for entertainment but deeply segregated.

Black performers like Davis could perform on major casino stages but were forced to stay in segregated hotels.

Sinatra used his clout to challenge these discriminatory policies.

He refused to perform unless Davis was allowed to stay in the same hotel room, forcing venues like the Sans Hotel to change their segregationist rules.

This advocacy not only benefited Davis but set a precedent for other Black artists.

 

In 1958, the legendary Rat Pack was formed, including Sinatra, Davis, Dean Martin, Peter Lawford, and Joey Bishop.

Originally called “The Clan,” Davis objected to the name’s association with the Ku Klux Klan, leading to the group’s rebranding as the Rat Pack.

Sinatra, as the leader, gave Davis space to express himself, though their onstage camaraderie often included racial jokes at Davis’s expense.

 

While the Rat Pack’s shows were wildly popular, Davis was sometimes the target of jokes about his skin color, voice, and appearance.

Though he laughed along on stage, behind the scenes, these moments caused discomfort and internal conflict.

Within the African-American community, Davis faced criticism and accusations of being an “Uncle Tom,” someone who endured humiliation to please white audiences.

Tensions peaked in 1959 when Davis publicly criticized Sinatra’s behavior during a radio interview.

Sinatra’s reaction was severe; he reportedly used racist language and fired Davis from the Rat Pack’s film *Never So Few*.

Davis found himself shut out from many opportunities controlled by Sinatra’s influence.

After attempts to reconcile, including interventions by Dean Martin and Peter Lawford, Davis was eventually welcomed back for the filming of *Ocean’s 11*.

However, the relationship was never quite the same.

Davis understood the power dynamics at play — Sinatra was the gatekeeper, and Davis had to tread carefully.

 

Despite their personal ups and downs, the 1960s saw both men actively involved in the civil rights movement.

Sinatra organized a benefit concert for Martin Luther King Jr. at Carnegie Hall in 1961, a landmark event bringing mainstream attention to civil rights.

Davis also performed at various events raising funds and awareness.

Sinatra used his influence to push for desegregation in Las Vegas hotels, famously halting a show when a Black couple was denied entry.

Davis witnessed these actions quietly, later acknowledging Sinatra’s leadership in advancing racial equality in entertainment.

 

Politically, both supported John F. Kennedy’s 1960 presidential campaign.

However, when Davis’s interracial marriage to white actress May Britt became public, Kennedy canceled Davis’s inaugural performance, fearing backlash in the South.

Sinatra was reportedly furious, distancing himself from the White House in protest.

 

In the 1970s, Sinatra shifted politically toward the Republican Party and became less vocal on racial issues, while Davis continued advocating for equality.

Their friendship endured, though more quietly.

In 1987, despite declining health, they reunited for a final Rat Pack tour with Liza Minnelli, symbolizing their lifelong bond.

 

When Sammy Davis Jr.died in 1990, Sinatra canceled all his performances and flew to California for the funeral.

As a pallbearer, Sinatra spoke simply but poignantly: “It’s hard to sum up a friendship of more than 40 years in a few words. I wish the world could have known Sammy the way I did.”

These words were seen as Sinatra’s ultimate affirmation of their complex but genuine friendship.

 

Their relationship has been revisited by scholars and journalists as an example of friendship transcending race, politics, and industry pressures.

Davis’s daughter, Tracy Davis, wrote about her father’s gratitude for Sinatra’s support, alongside the emotional toll of the jokes and control he endured.

 

Rumors about the nature of their relationship, including speculation about sexuality and power dynamics, remain unsubstantiated.

FBI files and historical records show no evidence of romantic involvement or remorse from Sinatra for his occasional harshness.

Instead, Sinatra’s consistent actions over decades—his protection, advocacy, and loyalty—paint a picture of a bond that was complicated but deeply rooted in respect.

 

Frank Sinatra’s final tribute to Sammy Davis Jr. encapsulates the essence of their relationship: a friendship that defied societal barriers and left an indelible mark on American culture.

Their story is a testament to the possibilities and limitations of racial progress in mid-century America and the enduring power of human connection.

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