"As a Republican, you have to have a narrative that talks about how you are actually doing work, how you are improving the lives of people," said Rick Wilson, a Florida-based GOP messaging consultant. "The value of the management asset associated with being in business has changed somewhat dramatically over time and that is difficult for Republicans. It used to be, 'He's a businessman, he has good values.'"
With the addition of Trump, and the anticipated candidacy of Ohio Gov. John Kasich, the current Republican primary will feature a quartet of contenders with past careers in finance or corporate America. It remains to be seen if any of them can do a better job than Romney in asserting the "business experience" raison d'être—or who among them will even try.
Jeb Bush has already been declared to have a "Mitt Romney problem," as Bloomberg Politics put it, due to his post-gubernatorial stint in offshore private equity.
Carly Fiorina, the former Hewlett-Packard CEO, lost her 2010 U.S. Senate bid amid a withering assault over her stewardship of the info tech giant.
Kasich, for his part, won the Ohio governor's race in 2010 despite his opponent's persistent attacks about his time at Lehman Brothers, where he served as a managing director until its collapse. He has since become a vocal critic of Wall Street's "greed," but has thus far refused to release his tax returns during his halcyon Lehman days.
And Trump is, well, Trump.
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Needless to say, there's a lot to pick at, and Democrats are already at it.
During her campaign kickoff speech, which themed generally on income inequality, Hillary Clinton also had specifics to say about American business; she uttered the word 14 times, according to the official transcript of the speech.
While Clinton warmly invoked her father's small drapery printing shop, and spoke of her campaign championing "small-business owners who took a risk," she noted the American public's distrust in big business and said, "Prosperity can't be just for CEOs and hedge fund managers."
A number of Republican operatives involved in the race expressed confidence that any effort by Clinton to Romney-cize their candidate or party in 2016, like Obama did in 2012, would be neutralized by the Clinton's own money-making over the last 15 years.
"It helps to have a presumptive nominee on the other side who is the epitome of the political class and the sort of reigning ideology of, this is due to me," Sarah Isgur Flores, Fiorina's deputy campaign manager, told CNBC.com.
It's worth noting the success Republicans enjoyed with a number of business-touting candidates in 2014, in both congressional and gubernatorial races. Perhaps the party's most impressive midterm victory was its takeover of Illinois, thanks to the self-funding financier, Bruce Rauner. (I previously wrote about Rauner's challenge in avoiding the Mitt Romney problem. Although the race went to a runoff, he ultimately prevailed.)
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Intriguingly, Rauner's campaign manager, Chip Englander, is now managing the presidential campaign of Kentucky Sen. Rand Paul, who has positioned himself as a bur in Wall Street's saddle.