How?

Donald Trump is here to stay.  He’s not going anywhere, and he’s not going to flame out like many (including me) predicted.  So it’s time that we start treating him like a real candidate.  That means it’s time to start asking the tough question.

And by tough question, I don’t mean gotcha style attack questions. Asking a presidential candidate who an obscure world leader is, for instance.  Total gotcha.  Asking them which newspapers they read?  Well, it can be a gotcha question for some people, apparently.  Hugh Hewitt was accused of asking Donald Trump a gotcha question when he asked about Iran and the internal working of the Iranian regime.  Whether that was a real gotcha question is in the eye of the beholder.

But there’s one tough question that few have been willing to ask Donald Trump – or, at the very least, few have been able to force him to answer.  And that’s a simple, one-word question that has the potential to derail his meteoric rise to the top of the polls.

How?

Trump has mastered the art of promising.  His speeches are rife with promises.  His articles are rife with promises.  Last night, in front of a crowd in Dallas he made dozens of promises. “I’m going to be so good to women, I’m going to be the best on women’s health issues,” he said at one point. “I’m going to build a great, great wall,” he said at another point.  We all know he wants Mexico to pay for that wall, too.

He says these kinds of things all the time.  It’s practically his trademark.  Here’s a few of the things he’s said in a similar vein:

“I will be the greatest representative of the Christians they’ve had in a long time.” – Trump on his faith in an interview from May 15, 2015.

“I will bring back jobs, I will strengthen our military, I’ll take care of our vets, I’ll get rid of Obamacare, which is, by the way, a catastrophe.” – Trump at the Iowa State Fair, August 15, 2015.

“We’re going to have so much money.” –  Trump discussing taking oil fields from ISIS on Meet the Press, August 16, 2015.

“We’re going to be reducing taxes for the middle class, but for the hedge fund guys, they’re going to be paying up.” – Trump discussing taxes on Face the Nation, September 13, 2015.

“Some of these illegal immigrants are gang members, they’re rough dudes. They’re going to be out of here so friggin’ fast…” – Trump talking about illegal immigration in Dallas, September 14, 2015.

We’ve heard from him over and over again the things he’s going to do.  Not once – not even once – have we heard how.

Trump is promising to do things that nobody has been able to figure out how to do – tax reform, repealing Obamacare, bringing back jobs, taking care of veterans.  These are all great things and things that every Republican candidate wants to do and has said they want to do.  Some of them have significant policy proposals that go into detail as to how they plan to get some of these things done. But we haven’t heard a single thing from him about how gets to where he wants to go. How is he, a political neophyte who has never held elected office, going to solve these apparently intractable problems that have stymied Washington for decades?  He needs to let us in on the secret, because many of us – including me – aren’t buying the promises.  They’re too similar to the other lies we’ve heard from so many other figures in the past.  How is he going to succeed where so many others have failed?

It’s great that Trump has a list of things he wants to accomplish in office. That’s a good sign, and his wish list is resonating with voters.  But as the old saying goes, you can wish in one hand and crap in the other, and see which one gets filled first.  Trump needs to start explaining how he’s going to get Democrats to go along with his agenda if he’s elected.  He has to start explaining how he’s going to be great on women’s issues while being “the greatest representative of the Christians” given how incompatible some women’s issue (like abortion) are with representing Christianity.  He has to start explaining how he’s going to reform the VA, how he’s going to deal with sequestration, how he’s going to rebuild a military while cutting taxes on the middle class and not ballooning the deficit.  He’s got to start explaining how he’s going to pay for this wish list, because all the hedge fund guys in the world don’t have enough money to fund everything he wants to do.

How?

That’s the question that’s going to hobble the Trump machine.  We need to start asking it.

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