The Secret Affair that Led to Frank Sinatra’s Banning from the Kennedy White House

In the lifetime of John F. Kennedy, he encountered numerous famous individuals, yet his most intriguing association was with entertainer Frank Sinatra, as depicted in Lee Server's biography, Handsome Johnny, focusing on West Coast mobster Johnny Rosselli.

The following account sheds light on why Sinatra was excluded from the Kennedy family fold.

The prevailing narrative surrounding Sinatra's expulsion from the inner circle of the Kennedys suggested that FBI's J. Edgar Hoover met with the attorney general before the president's Palm Springs retreat to caution him about Sinatra's ties with Sam Giancana and other mobsters.

Allegedly, Bobby, shocked by this revelation, hurried to Jack in the Oval Office, urging him to cut off all communication with the singer.

While the sequence of events appears largely accurate, it seems improbable that Bobby, or anyone informed by news or gossip columns for the past two decades, remained oblivious to Sinatra's connections with the Mob.

If Sinatra's affiliations had not stirred trouble for the administration until then, why did it suddenly become a point of contention?

An alternative version of the story, with a more plausible and personal angle for Bobby's abrupt decision to sever ties with Sinatra, emerged through Joe Shimon, a DC police detective with close ties to the FBI, Giancana, and Rosselli.

According to Shimon, Hoover presented Bobby with recent audio recordings from Giancana's tapped phones, featuring private conversations between Giancana and Sinatra.

The gangster pressing Sinatra for government favors, while Sinatra vowed to help.

The language was explicit and unsavory.

It became apparent that Sinatra was romantically involved with Pat Kennedy Lawford, the president's sister (wife of Peter).

In exchange for her influence on the brothers, Sinatra declared he would persist in this relationship.

Shimon recounted, “The tapes were played to Bobby, and he reacted with astonishment.

Overnight, Sinatra was out.

No more White House visits.

Complete isolation.”

With Joe Kennedy sidelined and Sinatra ousted, the Mob's hopes for leveraging electoral benefits dwindled.

The government's crackdown on crime persisted, leading to financial losses, arrests, and Giancana's growing resentment.

By June '63, Giancana resorted to legal action, suing the FBI for harassment and privacy violations.

Despite the Feds' refusal to participate, believing the court lacked jurisdiction, Giancana secured a victory.

The Chicago judge issued an injunction limiting FBI surveillance, specifying boundaries around his home and golf outings.

However, this triumph was short-lived as subsequent rulings revoked these constraints, reinstating the surveillance that troubled Giancana.

In defiance, Giancana refused to comply with directives, vowing to retaliate using his own methods if provoked.

The tumultuous relationship between the Mob and the authorities continued unabated, with Giancana's resilience against governmental interference remaining steadfast.