Elections are won and lost on simple concepts that extend from the candidate's personal brand and how that brand intersects with external events. So, who has the brand that will resonate better with voters: Hillary Clinton or Donald Trump ?

Hillary Clinton's brand is endurance. She endured endless humiliations from her husband's reckless affairs. She endured two presidential elections and Clinton administrations in the 1990s, Whitewater, her health-care reform debacle, the Lewinsky scandal, two Senate campaigns, a failed presidential bid, a controversial term as Secretary of State, including Benghazi, and the recent email scandal. Her capacity for sheer endurance is a skill in and of itself that must be acknowledged even if it is not always admired.

Donald Trump's political brand is entertainment. He is, at root, a reality star, a rapper who raps about being a brilliant businessman on television. Trump was a reality star before reality TV and a rapper before rap mainstreamed. The twin pillars of Trump's rap are obscene braggadocio and obsessive ridicule of resonant targets. While, as a citizen, I can barely tolerate typing his name, as a professional in the reputation racket, it's impossible to deny that he has gotten very far on his rap. Having a tycoon father backing him in New York real estate didn't hurt.

In positioning wars you're not only trying to drive up your own assets, you must drive up your opponent's liabilities. You seek to unravel your opponent's brand.

So, what are Hillary Clinton's pitfalls? In the past, she has steadily absorbed attacks when accused of wrongdoing and that has earned her public sympathy. Even her misdirection when under fire has been tolerated as an acceptable response to ceaseless assaults. But nobody wants to elect a president they feel sorry for. If Trump browbeats Clinton during the debates, she won't earn a big sympathy dividend. She has to hit back hard. However, she has to be careful not to respond to attacks with her penchant for seeming exasperated that we're too stupid to understand why she shouldn't be president by now. If she does, Trump will score points.

Meanwhile, Trump is the sum total of his pathological insecurities. He cannot abide criticism from even the most collateral parties and one imagines him wanting to use the nation's intelligence services to track down and punish someone who called him a doody-face in third grade. He flirts with psychosis at the very suggestion by reporters that he may not be a billionaire. Entertainers exorcise their insecurities in their art, but if your rap is that you're a larger-than-life mogul, you can't be seen as a panicked adolescent. Team Clinton will try to show the American public that Trump is the "little man behind the curtain," not the great and powerful Wizard of Commerce.

Part of Trump's authority as an entertainer is that he connects with regular people who worship celebrity and want to be a part of it, even if just through voting. Based on numerous public reports, Trump has a big weakness here in the embodiment of such regular people who either worked for him and claim not to have been paid, but also consumers of his products such as Trump University who say they were rooked. One of the reasons why Trump's attack on a judge of Mexican heritage resonated was because it was the act of a plutocrat who thought he should be above the law, the very thing he accuses Hillary of. Expect Hillary's marketers to hit Trump's attacks on the little people hard — and with examples.

While other presidents have possessed the traits of entertainers — Kennedy, Reagan, Obama — shtick alone didn't put them there. Trump's entertainment rap will likely bring about a surge for him in the weeks ahead because his gift for spectacle will energize a big chunk of the electorate demanding to be heard.

The "endurance" brand has always been strong in presidential politics. So, if we're going on brand, Clinton has the better chance of winning in November. However, if she does win, it won't be due to the kind of enthusiasm that Obama generated in 2008, but because voters believe her capacity to endure withering scrutiny on the national stage for a quarter century shows that she's not out of her mind, which is a point of differentiation from her opponent. Remember, Americans have elected unlovable personalities before, most famously Richard Nixon.

When it's all over, I think voters will prefer a serious candidate with serious flaws over a reality TV rapper.

Commentary by Eric Dezenhall, CEO of Dezenhall Resources, a crisis-management firm in Washington, DC. He is also the author of "Glass Jaw: A Manifesto for Defending Fragile Reputations in an Age of Instant Scandal." Follow him on Twitter @EricDezenhall.

For more insight from CNBC contributors, follow @CNBCopinion on Twitter.