06/08/2012 11:19 am ET Updated Aug 08, 2012

The Second Time Around: Don't Underestimate Barack

The nexus between big time entertainment and politics is nothing new. Ever wonder why the defining event of the 1930s, the Great Depression, never appeared onscreen in mainstream Hollywood movies during that decade? Strange or not, politicians and entertainers are constant bedfellows. So when syndicated columnist Kathleen Parker recently compared Barack Obama and Bill Clinton to Frank Sinatra and Dean Martin, I was eager to follow her argument. See, I don't know a lot about our current and former presidents, but I know an awful lot about the Chairman and Dino. And I think Ms. Parker, along with a great many other people, is missing one crucial point.

I should clarify that Ms. Parker's ultimate thesis seems to be that President Obama cannot run against "big money" while palling around with wealthy entertainers. And since I just admitted I don't know much about politics, I won't dispute her point. But I do know this much: Barack Obama has demonstrated, in a very brief time, more political savvy and realpolitik know-how than Frank Sinatra ever had.

Sinatra considered himself a great friend of the Kennedys -- this despite Robert Kennedy's aggressive investigation into the world of organized crime. The targets of his investigations, most notably Teamster president Jimmy Hoffa, were often, like Sinatra and Martin, of Italian descent. This put Sinatra in an awkward position but he nonetheless actively supported John Kennedy in his presidential run. Depending on who you believe, Sinatra, and the cash and influence he was able to commandeer from the Italian-American community, may or may not have been instrumental in electing Kennedy.

In return for this support, Sinatra was hoping for validation. He didn't want a political appointment (though Martin did claim that Kennedy had named him Secretary of Liquor), and if he wanted money or power, he saw them largely as by-products. He wanted respect, the kind of mainstream, cultured respect that no number of gold records and bedded starlets could bring to a skinny Italian kid from Hoboken. Sinatra hoped that a friendship with the Kennedy family would do the trick.

John made Bobby his attorney general and largely restricted further association with Sinatra. Sinatra was not exactly broken by the snub, but he was disappointed and most likely disillusioned. The Italian kid from Hoboken would never be a welcome guest at the Whitest of all Houses.

Less than fifty years later, the African-American kid from Honolulu would not only be a welcome guest; he would be the master of the house. Barack Obama's achievement in 2008 still has not been put in proper perspective. Consider this: at the 1960 Democratic National Convention, Sinatra, Martin and the rest of the Rat Pack performed the Star Spangled Banner. There were delegates present who insisted that Sammy Davis, Jr., the black Rat Packer, not be allowed onstage. This is the kind of embedded prejudice Obama had to overcome in 2008.

Those who underestimate Barack Obama's political instincts and savvy make a great mistake. He may not defeat Mitt Romney. The winner of that election may well be determined by events that are out of both candidates' hands. But to think he will make the same miscalculation as Sinatra, that proximity to celebrity bestows a false sense of entitlement... well, you can call me irresponsible, but I expect Obama will still be able to make the case that the country should have high hopes, that the best is yet to come.