For more than 50 years, Sinatra was a friend to presidents. But along the way, he made a political U-turn after a bitter falling-out with JFK.
Mr. Kennedy cut off ties with Sinatra in 1962 because of the singer's reputed mob ties, and "from there on in, it was no longer Frank Sinatra, Democrat; it was Frank Sinatra, Republican," says columnist Army Archerd of Daily Variety.
Sinatra would be back in the good graces of the White House in years to come as presidents decided Sinatra's star power outweighed any liabilities.
Author Garry Wills credits Sinatra with "a neglected masterpiece of political recovery."
Sinatra chaired the Reagan inaugural committee in 1980 and became a White House intimate once again.
"No one but Sinatra has been such an intimate of a Democratic president, then fallen from favor and become even more at home in the White House of a Republican successor," Wills wrote in "Reagan's America."
President Clinton said after Sinatra's death that he never met the singer before taking office. They had dinner since then, and Mr. Clinton said he had a chance "to appreciate on a personal level what hundreds of millions of people around the world, including me, appreciated from afar."
Sinatra's association with presidents dates to 1944. Already a superstar, the crooner visited the White House to offer his support to Franklin Roosevelt's re-election campaign.
Mr. Roosevelt reportedly asked him, "What's on the Hit Parade this week, Frank?" David Hanna wrote in "Sinatra Ol' Blue Eyes Remembered."
Sinatra went on to support Harry Truman even when the odds favored Thomas Dewey, and he was active in Democrat Adlai Stevenson's losing presidential campaigns before signing on with Mr. Kennedy.
"Dad felt that Jack Kennedy was a breath of fresh air," Tina Sinatra said in Seymour Hersh's book, "The Dark Side of Camelot." "He hadn't been as excited about an election since Roosevelt."
Sinatra organized Mr. Kennedy's inaugural gala and became a knight at Camelot's round table.
Mr. Kennedy cut Sinatra off in 1962 at the urging of his brother, Attorney General Robert F. Kennedy, who had seen the FBI files on the singer.
The snub became all the more humiliating for Sinatra when Kennedy stayed at the Palm Desert house of rival crooner Bing Crosby, a Republican. Sinatra's helipad went unused.
So started Sinatra's political turnaround. The man who once helped engineer Kenned's victory became a supporter of onetime Kennedy rival Richard Nixon.
Sinatra's star appeal is evident in a 1971 memo between Nixon presidential aides: "He has the muscle to bring along a lot of the younger lights."
Charles W. Colson wrote of Sinatra: "If we are going to cultivate him, as I believe we should (I also recognize the negatives) then he should very shortly be invited to the White House to entertain."
Mr. Nixon in 1973 became the first president to have Sinatra perform at the White House.
Sinatra "had tears in his eyes when he thanked me afterward," Nixon later wrote.
By the time Ronald Reagan was in the White House, Sinatra was back on top politically. Nancy Reagan, who liked to call him "Frances Albert," consulted him on entertaining at the White House and blew him a kiss on inauguration night.
Recalling those years, the Reagans on Friday said in a statement: "We will never forget when Frank performed at our inaugural celebrations - it made those evenings that much more special to the both of us."