Read More Mexico to Donald Trump: You are one 'ignorant,' 'prejudiced' hombre
While the strategy may have given him a bump in political popularity—he trails only front runner Jeb Bush in the latest CNN/ORC national poll of GOP presidential hopefuls—several public relations and brand strategists believe the statements will severely affect Trump's businesses and personal brand, with one industry insider, who asked to remain anonymous, saying it was "the equivalent of professional suicide."
"For businesses and brands, it's one thing to be associated with a divisive and disrespectful force that you don't as a company believe in, but when you combine that with moronic behavior it's a double whammy," said Lenny Stern, former political consultant and partner at agency SS+K. "It's the idiocy of his statements and how he's handled it."
Trump did not immediately respond to a request by CNBC.com for comment.
According to his Q Score—a industry standard measurement of the public's familiarity and reaction to a brand—Trump has always had a low positive score, meaning the majority of people sampled enjoy criticizing him.
But Henry Schafer, executive vice president at Q Scores Company, explained that it doesn't necessarily lead to bad business. When one trends negative in the public, they can build a successful brand out of upsetting and inflammatory stunts. For example, he pointed out that the Kardashian women also tend to have low Q scores despite the fact that Kim has been estimated to be worth $52.5 million, according to Forbes.
Read MoreWhy you should fear Donald Trump
What's more, Trump's strategy of being the man people bond together over due to collective contempt seems to have worked in the past, if you believe the self-reported fact that his net worth is $8.7 billion.
"They create the love-to-hate relationship," Schafer said.
At this point, it is virtually impossible to estimate exactly how much in dollars these lost business relationships will cost Trump. And even with this modus operandi, there is such a thing as going too far, said Stern, whose company worked on the Obama/Biden 2012 campaign.
"It's served him well in his personal endeavors and business," Stern said. "But what we find is that brands, politicians and businesses can quickly go off the deep end."