Until now, Donald Trump has defied all the expectations. Most of the political experts predicted he would be one of the media-fueled candidates who have emerged in last few primary seasons, propped up by intense coverage and then deflated when reporters turned their attention to another candidate.
The Donald has proven to be a much more durable candidate than they expected, maintaining a strong position in national polls as well as in local polling in key primary states such as New Hampshire. He has demonstrated tremendous savvy in keeping the media’s attention for a sustained period of time, which is not a total surprise given his deep experience on “The Apprentice” as well as the dynamics of what I have called the click-bait primary, where incendiary statements are more likely to win attention than to receive widespread rebuke.
But the Republican campaign is starting to enter a new phase where there are a number of questions about how Trump will fare. Now that the early phase of the competition will soon wind down — a free-for-all primarily revolving around televised debates — Trump will have to prove his chops if he is to win in Iowa, New Hampshire and the primaries that follow.
The most pertinent question has to do with grass-roots organization. In less than three months, the voting will actually begin. When it comes to the caucuses and primaries, old-fashioned retail politics still matters. As Barack Obama proved in 2008, the winner of these contests needs to put together a formidable grass-roots organization to mobilize and bring out the vote.
In a few states like Iowa, Trump’s campaign has given indications that it understand this. It has brought on some talented figures and started to put together a campaign. In Iowa, Trump scored a success by hiring Chuck Laudner, the grass-roots campaign operative who put together Rick Santorum’s surprise victory there in 2012, to handle his operations.
But it is not yet clear whether Trump is willing to devote the money or can devote the kind of day-to-day appearances that the campaign will require, and how well-organized his strategic voter mobilization plan will be. Tim Fernholz reported, for instance, that Trump had not even purchased some of the basic voter information databases that are prerequisites for victory.
Trump has made a point of saying he is self-funding his campaign, trying to draw a contrast with his rivals. While it is true he used some of his money, donations are still funding a lot of his campaign, and it’s not clear how much of his fortune he is willing to commit to this effort, particularly if his odds of winning start to diminish.
Soon Trump will also have to contend with an actual establishment candidate. The leaders of the Republican Party are starting to coalesce around a main candidate, very likely Sen. Marco Rubio. Trump has thrived in part because the GOP did not yet have a central candidate upon whom to shower its resources and energy. The divisions and uncertainty that have resulted from Jeb Bush’s poor run have opened up room in the campaign for some of the “outsiders” who have gained support.
If party leaders settle on Rubio, or Bush somehow engineers a miraculous comeback, the pressure against outsiders such as Trump will intensify. The party leaders will do much more, through their candidate, to unload blistering political and personal attacks on opponents within the party. Most recently, The Wall Street Journal, a scion of the Republican establishment, published a scathing editorial about how little Trump seemed to know about what was in the Trans-Pacific Partnership deal. When Trump responded by calling the editors “dummies” through a tweet, the paper stood by its comments.
If Trump is able to transition to the next phase with his standing in the polls intact, the media still have a lot of exposing to do. Everyone who has followed him since he made a splash on the national scene in 1980s New York as a “greed is good” real estate mogul knows there is a long record to explore.
Despite all the attention he has received thus far, the scrutiny has been relatively contained. Ironically, the fame with which he entered into the contest has diminished the incentive of some reporters to dig more deeply into his life. It is a contrast with candidates such as Ben Carson about whom the media didn’t really know much. That made reporters more curious to figure it out. With Trump, and the assumption we know everything there is about him, there has not been as much investigation as we might expect. But if he remains a serious candidate, more scrutiny will focus on his failed business ventures and his rocky marriages.
There are a number of important issues that have barely made it onto the radar. For example, a handful of reports have surfaced on how little Trump has given to charity over the years, a measure for the values of a wealthy person who has not been in public service, and the ways in which he has greatly exaggerated and misconstrued the money that he has donated.
The Associated Press produced a scathing report in August showing how he has overstated his contributions, how they are small compared with others of his income status, and that they advance his personal interests. This record would not sit well with some voters, who are seeking a populist voice, especially from a billionaire candidate who is now insisting that the wages of workers are too high.
His recent attacks on Carson, such as comparing what he called the neurosurgeon’s “pathological temper” to the sickness of a “child molester” have offered a reminder as to just how nasty the thin-skinned businessman can become against his opponents.
There are also questions about Trump himself. Thus far he has clearly enjoyed the ride. Yet it is not evident how he will feel as the campaign slog really gets going, with the brutal hours that it requires, and if he starts to fall from his plateau. It is not clear how passionate Trump is about the job and the kind of commitment winning a presidential race requires.
He has already made some comments about his willingness to quit if he is not doing well. In October, he told “Meet the Press”: “I’m not a masochist. And if I was dropping in the polls, where I saw that I wasn’t going to win, why would I continue?”
He gives off a different sentiment than some of the other candidates, such as Rubio, who are clearly willing to invest everything they have for as long as they are still viable.
For those who have always doubted whether this is about promoting his brand name as opposed to promoting a vision for the White House, there are doubts about whether he might just be willing to fire himself if this process turned unpleasant.
The brutal terrorist attacks in Paris this weekend are also a stark reminder of the immense security challenges that the United States and the world faces. These are serious times that call for extraordinary leaders. In this context, Trump’s yelling and insults, combined with questions about whether he would really be up for this job, are likely to become bigger liabilities among voters.
It is clear Trump has the potential to survive over the long run, and the state of the Republican Party might give him room to make it much further than anyone suspected. But the going is about to get a lot tougher, and the challenges Trump will have to overcome will intensify in the next few months.