Transcript: Rick Wilson, GOP Strategist


The transcript from this week’s MIB: Rick Wilson, GOP Strategist, is below

You can stream/download the full conversation, including the podcast extras on iTunesBloombergOvercast, and Stitcher. Our earlier podcasts can all be found at iTunesStitcherOvercast, and Bloomberg.


BARRY RITHOLTZ, HOST MASTERS IN BUSINESS:  I have an extra special guest this week, his name is Rick Wilson, he is a Republican political strategist, media consultant, and author who has produced numerous television commercials for governors, Senate candidates, super PACs, corporations, he helped campaign for Connie Mack for the Florida 1988 Senate campaign, he was George HW Bush’s field director in Florida, he was a presidential appointee to the Department of Defense under Dick Cheney, he created a number of award-winning ads for Rudolph Giuliani in the 1997 mayoral election, also campaigned for Giuliani for the 2000 Senate seat and he is the author of “Everything Trump Touches Dies, a Republican Strategist Gets Real About the Worst President Ever.”

Rick Wilson, welcome to Bloomberg.

RICK WILSON, REPUBLICAN POLITICAL STRATEGIST:  Well, thank you, Barry, I appreciate that.  I’ve been looking forward to this but I got to ask you, what’s your beef with Trump?  He’s making America great again.

WILSON:  Well, that’s a great catchphrase, Barry, but it’s also at variance with a lot of the things that I as a conservative believe in.

RITHOLTZ:  Okay, give us some examples.

WILSON:  Limiting the size of government, engaging in a in a trade war that is ultimately going to end as all trade wars do with a complete economic and political disaster, but look Donald Trump isn’t a conservative in the traditional way, he is more of a statist, more of an authoritarian, and is definitely some stuff that I have a lot of issues with as a conservative.

There’s nothing that Donald Trump’s character has ever indicated that he has any of the traits of moral probity or personal responsibility or accountability or integrity and so there were a lot of these reasons that I thought the Trump would be a damaging force in the country, not only for conservatism, but for our economy and for our system of government, and I’ve been I’ve been proven pretty consistently right on this over the last two years.

RITHOLTZ:  I have to admit, I was pretty shocked, I’m a lifelong New Yorker everybody in New York kind of knows what Trump’s gig is…

WILSON:  Of course.

RITHOLTZ:  It’s no big surprise, we all either know someone who’s worked with him or have been involved with one of his properties or been sued by him and I was shocked at how easily the right wing just bought his line when it was clearly nonsense…

WILSON:  You know …

RITHOLTZ:  At least about being a conservative, a fiscal conservative, et cetera.

WILSON:  Exactly, you know and my New York experience started in ’97 working for Rudy in the first in the reelection campaign and then I was here in City Hall for about a year working as an advisor and then on the campaign against Hillary.  So I got enough of a taste of New York at that point to get to where people read Donald Trump and how they scanned him, and it was always like, yes, the guy’s kind of a whatever but we’ll throw him some parking passes once in a while but …


WILSON:  And his ascent politically from people here and other folks that have done business with them and that I know in Florida and elsewhere, they were always stunned like how is anyone buying this con?  How does anyone believe this guy?  This BS is — everybody knows he’s bankrupt constantly …

RITHOLTZ:  Multiple times.

WILSON:  Everyone knows this guy is in debt up to his eyeballs, that this is all a character he’s playing on TV and not the real guy, you know, all this idea that Trump is one of the wealthiest men in the world and he’s an amazing businessman, a masterful negotiator, all these things, it’s all BS, it’s all crap and they all knew it and yes …

RITHOLTZ:  Then why jump on the Trump train?

WILSON:  Well …

RITHOLTZ:  Was it just raw attraction to power and not a lot more than that?

WILSON:  Trump identified something in the Republican base that they really wanted, they wanted someone who was so transgressive who was going to blow up everything because there’s a huge sense of inferiority in the Republican base, they really dislike the fact that the educated elites and the Ivy League people “look down” on them so and has been stoked over the years by Fox and by the right wing talk radio circuit…


WILSON:  And so those folks have the sense that Donald Trump was going to be this as I said, a transgressive and destructive force for the establishment, which they hate, they hate the establishment, Republicans, more than they hate Democrats.  They have a greater anxiety about their own party’s internal “elites” than they do about the Democrats.  And so Trump activated that very brilliantly and the Republican elected officials who followed along in his wake did it for two reasons, the first reason and I would say about, you know, in the house there used to be, a lot fewer today, a lot of those guys were just afraid of him, they are afraid of the Twitter feed, they’re afraid of his followers, they are afraid of the crazy train, they’re afraid of the people that Trump inspires.

RITHOLTZ:  You write about that in “Everything Trump Touches Dies” that there is a genuine fear amongst rank-and-file Republicans…

WILSON:  Absolutely.

RITHOLTZ:  That if this guy comes after me on Twitter, my life is over.

WILSON:  Yes, they have a political fear that they’ll be primaried by some nutcase, they have …

RITHOLTZ:  To their own rights…

WILSON:  Or to the Trump zone, from the Trump zone, they have a…

RITHOLTZ:  State run media is what they call that.

WILSON:  There is a there is a deep sense that a lot of the followers of Trump are the guys who are going to come to your town hall meeting and lose their minds with you and I told a story in the book of a guy who went to one of the first town hall meetings and he was asked “are you going to support the president 100 percent of the time?” and he says, “Well, I want to, I’m a Republican, I hope we can agree on a lot of things but, you know, I’m going to …”

RITHOLTZ:  I’m not taking a blind loyalty …


WILSON:  “I’m going to stand up for my district first.”


WILSON:  And he said, “No, no, are you going to support Mr. Trump 100 percent of the time?”  And he says no, moves on to the next question, by the time he gets offstage, his Facebook page is filled up with death threats …


WILSON:  His wife’s business Facebook page is filled up with death threats, his Twitter feed is a mess, his kids’ school is getting phone calls the next day and it’s because…

RITHOLTZ:  Seems appropriate, balance …

WILSON:  Yes, seems like a normal political discourse, right?

RITHOLTZ:  Measured, right.

WILSON:  But that it comes down to this point where the vast majority of the members of the caucus are just afraid, they are afraid of what Trump is going to say or do, there’s a handful of them who are true believers, there are a few these guys who really  have all the Kool-Aid…

RITHOLTZ:  Devin Nunes is perfect example.

WILSON:  Well Devin Nunes is a perfect example, Dana Rohrabacher, perfect, well, you know …

RITHOLTZ:  And we could discuss his district said “you’re not putting your district first, crossed him out.”

WILSON:  Correct.

And that is something that you know, that is something that we saw in this election.

RITHOLTZ:  Let’s talk a little bit about the GOP and there were so many questions that I had as I was reading the book, the first of which was what was the response from your fellow Republicans when you pretty much declared “Hey, this guy is not a Republican, he’s an imposter and he will destroy the party if you make him your nominee.”  There had to be some pretty fierce pushback.

WILSON:  In the beginning, not at all.

RITHOLTZ:  Really?

WILSON:  In the beginning, it was you are absolutely right, were all in this together and one by one they fell to the conformity of DC, which is a corporate town …


WILSON:  And a lot of them were dependent on work from the RNC or the NRCC or the Senate committee of the Governors Association and so they slowly shut their mouth, sat down, made their peace with the Trump world, and look, I have had a very successful career, I’ve done super PAC work for the last 10 years, I’ve done campaigns in 38 states, I’ve been to the rodeo, I wasn’t really you know subject to a lot of the same motivations that they were of, you know, keeping the mortgage payments up on their $5 million homes in Georgetown, right?


WILSON:  So I have a slightly different take on some of that, but it’s also that I’ve never tried to be one of the DC guys, they were all centrist Republicans and compassionate conservatives when George Bush was president …


WILSON:  And the minute the Tea Party won, they were all hair on fire libertarians, we were going to burn down the government, drown it in the bathtub and we were going to adhere to the Constitution strictly.

RITHOLTZ: That sort of ethical …

WILSON:  Flexibility?

RITHOLTZ:  I mean is it that blatant?  Is it that obviously?

WILSON:  In DC, it’s not even just that obvious, part of the trick for the lobbyist people was they basically had to hire Trump people to make good with the Trump family and the Trump organization.  A lot of these people in DC who hated Donald Trump with the fire of a million suns, to keep their RNC contracts, suddenly were they were hiring all these you know cats and dogs that wandered in from the Trump world who couldn’t have gotten a job at a Burger King otherwise and pretending that this was — that they had always been Trump, they had always been all about MAGA.

RITHOLTZ:  So when did the push back to you start in earnest?  When did you really start to have the GOP rank-and-file turn on you?

WILSON:  While on the frontend, a lot of them have said publicly, we are not working with Rick anymore, a lot of them still talk to me and I have taken on this weird role of like a father confessor to some of these Republicans for the last two years and they will call me up and say, “I hate him, I hate him, I can’t stand this guy, he is destroying the country” and the next day they’re sitting around the cabin off the Cabinet room table or they are wearing a red hat at a rally right because they’re just afraid.

RITHOLTZ:  Right, so they won’t even vote against him.

WILSON:  No, no, the fear defines them and this desire to please his base defines them these days.

And so look, once he got the nomination, I was definitely out of the family picnic list for a while, but I have spent the last two years speaking freely and making a critique of Trump from the right and honestly, I’m liberated.

RITHOLTZ:  You don’t have especially kind things to say about Reince in the book.

WILSON:  I don’t because he had every opportunity to pull the circuit breakers on Trump …

RITHOLTZ:  Early.  Way early.

WILSON:  Early, yes.

RITHOLTZ:  Why didn’t he?

WILSON:  I think in many ways he feared that Donald Trump would “leave the party”

RITHOLTZ:  Go to the Democrats?

WILSON:  No, and run as an independent and therefore would tap off a small but meaningful percentage in enough states that Hillary would be in sure to win, that was what one of his advisers said to me at the time and I said …

RITHOLTZ:  Is that an unreasonable position?  It seems fairly logical.

WILSON:  Well the thing about it is Donald at that point would not be able to raise money from the Republican sucker base who loved him, he would’ve had actually spend his own money for real.

RITHOLTZ:  And we know he didn’t want to do that.

WILSON:  He never does, he doesn’t have any money to spend.

RITHOLTZ:  So my pet thesis about Trump this whole time has been 2012 was a phenomenal branding opportunity for him, he ran, he raised his profile, everything he did financially after that was a big win for him, I looked at 2016 as he has no interest in winning, he just wants to take all the free publicity …

WILSON:  Of course, and the people inside Trump’s campaign for the last month of the campaign, “I can’t wait until this is over, we are going to go have a big steak dinner, I got to tell you the crazy stories about this idiot” and on election night, Steve Bannon Reince Priebus, Kellyanne Conway, all the senior Trump staffers are calling every reporter in the country saying, “It’s his fault, it’s her fault, it’s their fault.”

RITHOLTZ:  They were already blaming each other before the results were in.

WILSON:  They were already brainstorming, this is at 4:45, I got a phone call …


WILSON:  … from a major national reporter who just said I just got off the phone with one of the president’s senior strategists who is today in the White House and this person told me “Bannon is an idiot and Reince blew this and they’re just morons and the family are a bunch of greedy mafia people, this is a cry — this is horrifying” and an hour and a half later, this person is on the stage waving and smiling because then I came up differently, they had no anticipation of winning at all.

RITHOLTZ:  You can tell from the lack of lists of senior cabinet people, ambassadors, there’s still hundreds of unfilled slots, it’s two years later.

WILSON:  Sure.

RITHOLTZ:  Take a look at the tax cuts, there’s no rhyme or — that was a Paul Ryan joint, that wasn’t a Donald Trump joint…

WILSON:  Right.

RITHOLTZ:  He just cares about the victory is how I read it and not the policy details.

WILSON:  He cares about the celebrity.


WILSON:  And that’s always been what motivates Trump, a friend of his, a former friend current friend, I’m not sure how you describe it, said to me one time, whatever makes him money, whatever puts him in the papers that day, that’s Donald Trump’s entire world.

RITHOLTZ:  Fame, money, and love, those are the three most …


WILSON:  I wouldn’t say love, yes.


RITHOLTZ:  I’m trying to put a nice spin on it.


RITHOLTZ:  So let’s talk about what the Democrats should be learning from this election cycle, what should I have done differently in 2016 and what should they be doing differently in 2020?

WILSON:  Well, I think what they learn this year to their credit and it’s taken a long road for them to get there is to try to nominate people for Congress who fit the district, for years though they had this very top-down approach were no matter who you are where you are running, you had to be the same Democrat that would be acceptable in Manhattan or …


RITHOLTZ:  Upper Westside Democrat.

WILSON:  Right you had to be completely pro choice, you had to be completely anti-gun, you had to be completely high taxes…

RITHOLTZ:  Purity test.

WILSON:  Purity test, all the ideological monoculture that Republicans like me used to defeat Democrats all over the country.  What they learned is you can you name an  Ocasio-Cortez in the Bronx.


WILSON:  But you got to name a Conor Lamb in Pennsylvania…

RITHOLTZ:  Makes sense.

WILSON:  In Western Pennsylvania in rural areas, the Democrats finally seem to have started to learn that a little bit this year and some of their more progressive candidates like Andrew Gillum in Florida, who you know, for all the people were very enamored of Andrew Gillum, he was very far to the left of where Florida is.

RITHOLTZ:  Still came within 1 percent, pretty shocking.

WILSON:  It was a very impressive campaign, he is an impressive candidate.  So a lot of them are progressive guys who felt like they started to check all those boxes, fell short, and the fact that 31 candidates that Donald Trump endorsed for the House, 28 of them lost.

RITHOLTZ:  That’s amazing.

WILSON:  Yes, the Trump…


RITHOLTZ:  That is a pretty thorough repudiation of the President.

WILSON:  Yes, the Trump hit on house campaigns is something that will have a longer political run out than the fact that they won some Senate races in states that where the Democrats were disproportionately holding those seats.  I mean Claire McCaskill …


WILSON:  In Missouri, that is a state that has trended redder and redder, Indiana deeper and deeper read all the time, and so you we’re shocked that people — that the Republicans won in North Dakota, Trump won the state by 32 points.

RITHOLTZ:  Wow.  So let’s talk about some of the changes from the prior election and you have to really begin with white college-educated suburban women, how significant was that group for Democrats losing the White House in 2016 and how important was it to this midterm election?

WILSON:  About 55 percent that voted for Donald Trump in 2016.

RITHOLTZ:  Isn’t that a kind of a shock?  That was surprising…


WILSON:  It was a kind of a shock.


RITHOLTZ:  But more than Mitt Romney.

WILSON:  But right away, right away, they realized there was an almost immediate …


WILSON:  Oops factor and the tone and in things like Charlottesville and the immigration, putting kids in cages, not a good look for suburban educated women, they are not really keen on it, so what you ended up with was they sort of got a separation in the fall and winter of 2016, and last night, the divorce was final, they walked away from the Republican Party in enormous numbers, we’re starting to feel through the exit polls, but if you look in places like Pennsylvania, the Democrats picked up four congressional seats there, almost all them in suburban areas where educated white women are the driving political force.

RITHOLTZ: So here’s the long-term question, did they walk away from Republicans or did they walk away from Trump?

WILSON:  Is there a difference anymore?

RITHOLTZ:  Well I imagine there is, so I am, I get grief from friends when I say I grew up a Jacob Javits Republican.

WILSON:  Sure.

RITHOLTZ:  Which is pretty middle-of-the-road, balanced-budget, low taxes, no overseas adventures like Vietnam or subsequently Iraq and keep the government the hell out of the bedroom, fairly moderate Republican…

WILSON:  Sure.

RITHOLTZ:  With the best part of the libertarian side, I haven’t changed, it’s just that the hard right part of the party has taken over and really driven things…

WILSON:  See, there’s a there’s a real desire that we sort of pretended wasn’t there for a long time, not for limited government and you know, the rule of law and low taxes and constitutional adherence, there’s been an appetite for sort of authoritarianism and a strongman bully character that’s been fed for a long time by the sort of talk radio culture…


WILSON:  And so we’ve ended up with know what people wanted, they want the id of the Republican Party not the superego.

RITHOLTZ:  Quite interesting, what keeps coming up all the time is that the country is so divided and part of me feels well Congress is divided but there are so many things that Americans seem to agree with, it almost feels like more and more of us are living in purple states then deeper read and deeper blue and while there are certainly exceptions to New York and California and Indiana and I was going to say Kansas but I guess I can’t say Kansas anymore.  How accurate is that media depiction?  Are we a nation divided her or are there more things that unite us than divide us?

WILSON:  When it comes to politics, the siloing off of Americans has divided us profoundly.

RITHOLTZ:  And what’s the cause of that?

WILSON:  The first is politics has become a reality television show that we are all living in and people every day are fed by the channels they like and by the news sources they like and the Internet has allowed people to silo themselves off into social groups.  Look, we’ve become a disintermediate society, we don’t do the things we used to do as people, we don’t we don’t have the same sort of us churches, social clubs, bowling leagues, baseball teams, all these things people used to doing together, what’s more important to them now is their Facebook group and they interact more with people through social media than they did before.

And so part of that whole it social media problem is that people want to portray this optimized image of themselves.


WILSON:  And to and to get attention in that attention economy social media and so they become flaming partisans, they become something visible inside their social group and so …

RITHOLTZ:  So that’s number one …

WILSON:  That is huge factor.

RITHOLTZ:  So we clearly have a divide set up by media.  Let’s talk about some of the other more interesting issues of the modern electoral campaign.

WILSON:  Sure.

RITHOLTZ:  The polling was under significant criticism in 2016, how’d they do in 2018?

WILSON:  A little better in some places but we’re still at a point where we chase these polling stories that are built on statistical models that don’t reflect what the turnout model is going to look like.

RITHOLTZ:  Which has to do with what?  Is it enthusiasm or just not being able to reach people who only have cell phones?


WILSON:  it’s not being able to reach people, it’s a lot of — there are a lot of mechanical and technical problems in polling now, they used to have to make a couple thousand phone calls to get a decent sample and now you have to make 10,000 phone calls to make it a decent sample, people don’t answer their cell phones from strange numbers they don’t recognize.

RITHOLTZ:  Because you just assume it’s someone calling to lower your credit card ball…


WILSON:  Right, it’s spam, it’s, you know, healthcare enrollment is open, everybody has gotten those calls, a million of them.


WILSON:  Landline phones are basically..

RITHOLTZ:  Don’t work…

WILSON:  Are basically old people.


WILSON:  66 plus, or you know, the chance of you owning a landline phone now, it means you are 60 or older, so there are a lot of technical difficulties in polling, we also are seeing some better analytics coming out using big data …

RITHOLTZ:  Big data, sure.

WILSON:  Using a lot of the things, I mean looked, it used to be you would take a random digit dial, if you call 600 or 800 people and you ask them polling questions.  Well then you sort of making that dial list off of the voter file, so you are really talking  to the people that are actually going to be there.  Then you started modeling that and saying okay, well, this guy’s record says he has voted in two of the last three primaries so we are going to definitely talk to him, he is unlikely, and now we’ve got consumer data, we’ve got click data from the Internet, we’ve got the ability to say, “Okay this guy reads Bloomberg every day and he reads on the Wall Street Journal every day and he looks at drug three times a day” so we know he’s an engaged person maybe the tax issue is the one we are going to talk to him about, we will ask him this question.

So there’s a lot of so that’s giving us an enriched picture for the voters are, but the guys I work with, my pollsters, I’ve been saying to people we are going to get 35 Democratic seats and two or three Republican pickups in the Senate…

RITHOLTZ:  That’s pretty good, that’s …


WILSON:  We were pretty happy with that and we didn’t feel like we missed a lot of big calls and I’ve been — you know, as a purple state guy, as a guy who still lives in Florida, I told people for weeks it’s going to be razor thin …


RITHOLTZ:  Within one percent.

WILSON:  Yes, its 30,000 votes…

RITHOLTZ:  That’s unbelievable.

WILSON:  In a state of 20 million people.

RITHOLTZ:  Let’s talk about Florida because what I haven’t seen a lot of people discussing has been the proposition that passed, namely if you’re a felon, and I think it’s nonviolent …

WILSON:  It’s nonviolent felon.

RITHOLTZ:  Nonviolent felon, throughout most of America, you go to jail and you lose the right to vote, it’s very much a disenfranchising situation that falls proportionally to people of color.

WILSON:  Absolutely.

RITHOLTZ:  Now there is something like 1.3 million …

WILSON:  1.4.

RITHOLTZ:  1.4 million felons in Florida who now will have the right to vote in 2020, and what does that do to the states dynamics?

WILSON:  Well it’s interesting, look I don’t think every single one of those people is going to become a likely voter.


WILSON:  I don’t think every single one of those people is necessarily going to be a Democratic voter, however I strongly supported this because I believe that our justice system, once your sentence is served ….


RITHOLTZ:  You have paid your debt, you are done.

WILSON:  That you paid your debt to society and you get to move on so I really think that in that with that particular amendment, it spoke to a fundamental sense of justice, it also spoke to something that in Florida we are one of the most putative states in the country on the criminal justice side, we put a lot of young black guys in jail, and we put a lot of them in jail for 1.01 ounces of marijuana.

RITHOLTZ:  Ounces.

WILSON:  Yes, we put a lot of them in jail in the 90s during the hyper enforcement of the crack epidemic, and I was part of the original right on crime movement where as conservatives we wanted to look at criminal justice in this country and was this an application of state power that was disproportionate particularly to African American men.


WILSON:  And it is.  It is unarguable that that is the case.  And as a conservative, I don’t want the state to have this punitive thing hanging over these guys heads for their entire lifespan, so I got an email last night from a guy who non-African American guy who had a low-level white-collar thing because I’m going to get to vote for the first time in 22 years, and this is a guy who’s been — who went to jail for two years and absolutely turned his life around in every conceivable way, the straightest arrow in the universe, and I was like that’s where this thing comes in.

You know, at some point where are we going to punish people forever and ever and look, it is vastly disproportionately African American men, I don’t know what the overall percentage is going to be of that 1.4 but I’m going to tell you it’s probably close to 60 percent

RITHOLTZ:  So let’s talk a little about voter suppression, there were all sorts of questions about voter suppression, I had no idea it was so prevalent in Texas, I read a big article, I think it was in the Atlantic but we have to talk about Georgia.  What took place in Georgia, somebody tweeted if this was a foreign country, the US would be …


WILSON:  An article from the Atlantic, yes.

I will say this, the things that were coming out of Georgia on election night shocked me.  And Brian Kemp’s self-interest in the case of I’m going to run an enforcement operation to make sure…

RITHOLTZ:  That benefits myself.

WILSON:  To make sure that I win this race, that does strike me as has as a little small of the third world around it.



RITHOLTZ:  So is this a viable issue for the Democrats to raise broadly that we should expand voting rights to everybody.

WILSON:  They can raise it, they can raise it, but it’s not cutting political issue, it’s a boutique issue, and what I would do if I were the Democrats is make sure that they were litigating the hell out of it which they need to, and if I were the Democrats in a lot of these states, I would make sure that they do more voter training and education so that people know their rights, I mean people being told, “Sorry, polls are closed now” and you’re standing in line, the courts have said time and time and time again that once you’re at a polling place…

RITHOLTZ:  And in line.

WILSON:  And you’re in line, you get to vote, easy lift, but a lot of people don’t know that.

RITHOLTZ:  Interesting.

WILSON:  Republicans have been very good at educating their voters to get out early, to vote absentee, to do early voting, Democrats need to do the same thing because it is harder to do it, it is harder to spread out the suppression effort over a week or two weeks of early voting than it is to do shenanigans on election day.

RITHOLTZ:  We have been speaking with Rick Wilson, he is the author of the “New York Times” best-selling book “Everything Trump Touches Dies” if you enjoyed this conversation, be sure and check out the podcast extras where we keep the tape rolling and continue discussing all things electoral-related, you can find that wherever your finer podcasts are sold, iTunes, Overcast, Stitcher or

We love your comments, feedback, and suggestions, write to us at, you can check out my daily column on, follow me on Twitter @Ritholtz.

I’m Barry Ritholtz, you’re listening to Masters in Business on Bloomberg Radio.

Welcome to the podcast.  Rick, thank you so much for doing this, I have to tell you, I’m like two thirds of the way through the book and it’s really hilarious.  You have not only a wonderful writing style but a vicious wit, I’m glad I never ran a campaign on the other side of you because you seem to have the ability to pull out the dagger and not only sticking in but twist it, let’s talk about some of the things that you mentioned in the book that I find absolutely fascinating and I have to begin with the tale of — “Congratulations, What to Expect When You Are Going To Work In The White House, A Tale In Five Pieces” it’s ironic but everything I read in that list, you can name a dozen people who must’ve gone through that.

WILSON:  Sure.

RITHOLTZ:  It’s pretty brutal.  What is it about Trump that just basically uses people and throws them away and yet there is still a line of people willing to get fed into the maw of the machine?

WILSON:  Well, I’m going to disagree with you on the last part, but I will loop back to that.  Trump is a bad manager, he is a bad leader, he is a bad person, he is a bad President.

RITHOLTZ:  How do you really feel?


WILSON:  I don’t know, you know…


RITHOLTZ:  You got to get…


WILSON:  To the side a little bit, right?


WILSON:  But the folks who go to work for this guy, they…

RITHOLTZ:  I mean they all get demolished.

WILSON:  They are every single person that goes into the White House loses their soul, their reputation, their ability to stand up straight.

RITHOLTZ:  I mean Rex Tillerson, that is just a shocking …

WILSON:  There are people that everyone thought would be fine, like Nikki Haley, she’s going to be fine, she’s worn out, she ran away.

RITHOLTZ:  Who wrote the anonymous letter?  You’ve any idea?

WILSON:  I have an idea but…

RITHOLTZ:  You’re going to keep it to yourself?

WILSON:  But I’m going to keep it to myself for now, because if it is who I think it is, it’s somebody who’s pretty senior okay and is not completely bought in.

RITHOLTZ:  You don’t want to out them?

WILSON:  I don’t want to out them.  Yes.

But I will say this, the story I told there that the what to expect when you’re working for Trump story, it’s a mildly fictionalized version of what we’ve observed over time and it’s also something that you guys that I knew who have done business with him here and in Florida told the same story…

RITHOLTZ:  Over and over again…

WILSON:  These yahoos that go in to work for Trump, and he promises “Well, you are going to be a billionaire too and it’s going to be great, and we’re all going to be driving Lamborghinis and they bust their ass for a few years, they do that one of these projects for him… ”

RITHOLTZ:  And then they don’t get paid.

WILSON:  They get shafted.

RITHOLTZ:  Right, it’s amazing when that story came out, there with 3,000 pending litigations from contractors who want to get paid.


RITHOLTZ:  I heard a wonderful story of a guy, I have a friend who worked in his legal department …

WILSON:  Okay.

RITHOLTZ:  Briefly and went back to a firm said it’s just insane, they needed this guy to get a certificate of occupancy and he basically said nope, you can sue me, you could do what you want, you will not get a CO, you could shut this whole project down, every day what you owe me o goes up, there is interest and penalties, my advice to you is to pay this tomorrow and other than that guy, I dont know anybody who’s been in that sort of dispute and actually got paid and yet people continue to line up although you are going to push back on that.

WILSON:  I will push back on that because Trump has had so much difficulty recruiting people who can walk and chew gum at the same time, he has surrounded himself with a subpar…

RITHOLTZ:  No doubt.

WILSON:  … group of people both in the cabinet and insight the White House itself, these guys are checked out, they are engaged in a constant war with each other all of them hate one another, with the constant leaking between Jared Kushner and John Kelly, and between Kellyanne and every other human being on Earth and then Sarah Sanders sniping at other people, these guys are all — this is a leakiest White House we’ve seen in ages.  I have a rule over time, it’s been proven pretty accurate, good White Houses leak on purpose, bad White Houses, and unhappy White Houses leak all the time.

This White House, this golden age of journalism we’re in is because everyone in the White House from the President on down is leaking to dog other people around them.  It is a — I mean the way the leaks that will come out after this election of everyone blaming Trump, they are going to be inside the White House and he can’t — he doesn’t get it, he’s blowing this, it’s going to hurt him in 2020 if he talks about a red wave which was his big conceit from weeks and weeks on end, there will be a red wave, we are going to gain seats in the house, it’s going to be great, we are going to have the best day ever, I’m the king of this, it didn’t quite work out that way.

But so all these folks inside the White House they’re constantly having their egos just ground up, they are constantly forced to go out and adopt public positions that they know are lies, that they know or anathema, they know will end up hurting their reputations in the long run, and yet, you know, the ones…

RITHOLTZ:  And yet they do it.

WILSON:  The ones who were stuck there are stuck there because you wouldn’t hire these people to manage a waffle house.

RITHOLTZ:  So you mentioned Jared and Ivanka, what’s with the nepotism and bringing the family in?  It just seems so at odds with everything we’ve learned about how do you ethically run a business.

WILSON:  But remember, the business of Trump is not government or patriotism or loyalty to the country or service to the American people, the business of Trump is Trump, and he doesn’t — he skipped that part of the constitutional we don’t do titles of royalty because he seriously considers himself to be some sort of a royal figure, above the law, above the Constitution, and the royal family idea is something that is clearly playing out here.

You have his fans who say things like well after Trump runs, then Don Junior will run, then Ivanka will run and then Eric will run and then Baron will run in the near in the far, far future…

RITHOLTZ:  They can’t be serious.

WILSON:  You know, the cult like devotion to the sky is one of the most shocking elements of Trumpism.

RITHOLTZ:  I agree.


WILSON:  It truly us.  Look, I love me some George W or George HW Bush, I love me some George Bush, I love me some Jeb Bush, the Bush family has been great to me and I have been loved back.  But you know what?  If one of them said to me “Go drink this poisoned Kool-Aid”, I wouldn’t do it.  But Trump could stack people up like Jonestown and they would do it, they — his line about shoot somebody on Fifth Avenue have the disadvantage for a country of being entirely true.

RITHOLTZ:  That is shocking.  Let me shift gears a little bit and ask you about the unspoken elephant in the room the past month, the Mueller investigation continues silently to grind forward.  My best guess is that — let me rephrase that, if I had to pick  somebody assuming I was running a sort of sketchy business and there are perhaps might have been some Russian involvement and maybe there is some money laundering, if I had to pick the one guy I didn’t want investigating me, it would pretty much be Robert Mueller, this guy was built to investigate Trump.  How does this play out?

WILSON:  The last two months, Robert Mueller made a very conscious decision to become a hunter submarine, he is under the water, he is listening, he is working, he knows where the targets.  Just because you don’t see him doesn’t mean he doesn’t mean he doesn’t see you.  This is a guy with a reputation for being methodical, for being diligent, for driving home, for going — for getting to the X of any operation.


WILSON:  And he’s got resources both on the intelligence side, on the financial investigatory side and on the legal side that the clown show around Donald Trump has never taken seriously and never understood and what happened with the election, Robert Mueller is protected now that Trump can’t just idly fire Robert Mueller and…

RITHOLTZ:  What happens if he does?

WILSON:  It is the apocalypse politically, you end up with a House Oversight Committee, hires Robert Mueller and …


RITHOLTZ:  Go ahead, let’s go.

WILSON:  And just go ahead.

Now they can also ask for Robert Mueller to provide them that report.

RITHOLTZ:  Which would not have happened in a GOP controlled …

WILSON:  Which would not have happed with Devin Nunes, and Goodlatte and those guys, it would never have happened, it would have never seen the light of day, there will be political consequences now and there is no defense operation where Nunes or Rohrabacher or Jordan or any of these guys, team obstruction, I call them…


WILSON:  There is no further ability for them now they’re not chairman to go out there and filibuster in these hearings to blast Robert Mueller and to blow up the FBI and to go and attack an assault an investigation and to look away from the involvement of Russia and try to manipulate our elections.

So what’s going to happen is that the shock and awe effect of further indictments is going to cause a sort of accelerating cycle.  Trump will get more and more crazed, by the way, I think Jeff Sessions is gone within a week, I think he’s outie.

RITHOLTZ:  Isn’t it — I was going to say, normally it is in the second term when it’s a turnover but you are just saying postelection, he’s gone.

WILSON:  Right, right.

RITHOLTZ:  Post midterm.

WILSON:  Post midterms I think he’s gone because Trump recognizes that the that the most dangerous window of time for him going forward is between right now and when the Democrats take power.  His actions in the next 90 days are to be very, very telling and it is going to be very, very dangerous for this country and that 60 days — excuse me.

RITHOLTZ:  So assume he asked Sessions to resign, if Session resigns he could do an interim appointment but if Session says, nope you got to fire me…

WILSON:  No, he’s going to have to fire Sessions, but I think Sessions will go.  I think he go.

RITHOLTZ:  In the next 60 days before the Democrats’ new legislative session…


WILSON:  Absolutely, and I will say this also, I know for — I know the White House have been shopping for a new AG and I know …

RITHOLTZ:  Well, you could see Lindsey Graham kissing up for that slot.

WILSON:  Yeah, but that the person that is rumored very heavily right now is Pam Bondi, the former AG of Florida…

RITHOLTZ:  Who by the way it when you look at the Florida foreclosure debacle…

WILSON:  Correct.

RITHOLTZ:  It was as corrupt as any public official ever.

WILSON:  Yes, I have spoken to Trump friendly Republicans in the Senate who are begging him do not name her.

RITHOLTZ:  She is going to open an amazing can of worms.

WILSON:  She cannot — she cannot be confirmed, do not name her.  So if he tries to name Pam Bondi as the AG I think there are going to be, there is going to be some very, very hard push back even from his own side, but the narrow window between now and when the Democrats are …

RITHOLTZ:  What’s the date of that?

WILSON:  The 21st.  The narrow window between now and then is to be a fact a very risky time, but I think he may buy himself more trouble if he does, I mean look, the guy’s already like knocking on the door of obstruction charges every side day.


WILSON:  So if he tries to play shenanigans between now and the time the Democrats have oversight ability, it’s going to be a real — it’s going to be a really ugly moment, and I think one of the things about the Democrats taking over that people are underestimating, they’re not as dumb as they look, they are not going to race…

RITHOLTZ:  Adam Shift is a pretty savvy guy.

WILSON:  They are not going to race to impeach Donald Trump, this is a death of a thousand cuts.

RITHOLTZ:  Right, that is right.

WILSON:  This is an easy, you know, we’re trying to throw the present out of office this is going to be we need your taxes now, we need to talk about your business dealings, we need about your dealings with Russia and Russian banks and Russian oligarchs, we need to talk about your meetings with the Russians, we need to talk about your communication with them, we need to talk about Cambridge Analytica and Steve Bannon, they are going to just peel this thing back one little strip at a time and it’s going to make Trump crazy.

RITHOLTZ:  Is he dangerous when he’s crazy?  Is he more dangerous I should say?

WILSON:  I think Trump is a danger to the rule of law in this country, and I think there been very few checks on him so far, I think he grew accustomed to being unaccountable.  And when people are accustomed to being unaccountable, they are dangerous.

RITHOLTZ:  Now you’ve been on the Bill Maher show, right?

WILSON:  A couple of times.

RITHOLTZ:  And Maher thinks that when it’s time for him to go, he’s not going to leave, I don’t buy into that, I think the mechanism of between the Secret Service and the military and the police, it’s going to be I don’t care what you say grandpa, here is the door.  I could be wrong but I doubt it.

WILSON:  That would be a hell of a moment, that would be a hell of a constitutional test in this country, the most severe constitutional test we’ve had since Nixon and it is a real question about whether Trump look, hypothesized that he is impeached for whatever purposes, they find video of Putin giving him a sack of money and you know let’s just hypothesize he gets impeached, it is going to be tough to drag him out of that room.  I think Bill is right about that.

But I think at the end…

RITHOLTZ:  But he will be impeached not convicted and so why bother?

WILSON:  Correct, correct.

In the end, the impeachment thing has always been a unicorn for Democrats…


RITHOLTZ:  I agree.

WILSON:  Okay, let’s suppose, they impeach him in the house, they could do it tomorrow.

RITHOLTZ:  So what?

WILSON:  You know, they could do it, how you get two thirds of the Senate?

RITHOLTZ:  You don’t.


RITHOLTZ:  You don’t even get to 50 percent of the senate.  So why alienate the people?

WILSON:  Correct, that’s why think they’re going to go and investigate and tear things open slowly and it’s going to look …

RITHOLTZ:  Make him unelectable in 2020.

WILSON:  This is an administration that is lavishly corrupt.

RITHOLTZ:  Lavishly corrupt, that is a good phrase.

WILSON:  They are so overt about it, I mean look at the coal guys, they basically took a shopping list to the White House with prices next to the things they wanted, and “well, you get a million dollars if you take care of this regulation and you will give the inaugural committee half a million if you will do this for this company.”  These guys are just brazen, they aren’t even pretending, and so…

RITHOLTZ:  And what about the  what about the emoluments clause, that’s got to be an issue that comes up.

WILSON:  It should be an issue that comes up and it will be I think and that is, I think, by the way, one of the venues where Donald Trump’s taxes become revealed, because how you know, we’ve got have an answer on that, and the only way we can really get that answer because you know, Donald Trump’s financial statements are always sort of mythical creatures…


WILSON:  You know, it’s man bear pig, it’s whatever he thinks up at that moment, “I am worth $10 billion because it I believe my brand is worth $7 billion.”


WILSON:  Okay, yes.

RITHOLTZ:  $8 billion in good will doesn’t count.

WILSON:  Brand equity is different than what you think it is, Donald, but you know so I think the emoluments stuff where this guy is obviously profiting off of lobbyists and look I know of tunnel lobbyists in DC, they are friends and …

RITHOLTZ:  Foreign countries going to Trumps hotels and et cetera.

WILSON:  The fact that they now go to the Trump Hotel to have all of their meetings and all of their events and they pay a gigantic premium, a gigantic premium, across the street at the Willard which is not exactly the Motel 6, everything in DC now has to go to the Trump properties and so that’s — it’s like such small crappy grift but it is grift, I mean it’s just discussing.

RITHOLTZ:  Are they going to have to disgorge those profits?

WILSON:  I don’t know if they have disgorge them but I think they have to disclose them and I think that’s what you get to the taxes in the emoluments…


RITHOLTZ:  That’s amazing.  I know I don’t have you forever so let me get to my favorite questions and our speed round, let’s plow through this.

WILSON:  Let’s do it.

RITHOLTZ:  What’s the most important thing people don’t know about Rick Wilson?

WILSON:  They don’t know that I am a hell of a cook.

RITHOLTZ:  Really?  Quite fascinating.

Who are some your early mentors?

WILSON:  Some of my early mentors, well this guy named Dick Cheney/

RITHOLTZ:  Really?

WILSON:  He was the Secretary of Defense, I mean you learn so much from him…

RITHOLTZ:  And vice president.

WILSON:  Well, and vice president later, there was a guy that I also worked for, a guy named Donald Rice who is a secretary of the Air Force.  One the most brilliant considered policy guys I have ever met my career.  And I’ve been I’ve been very fortunate over the years to learn from great people.  In New York are Ray Harding who was the chairman of the New York Liberal Party, which is Ray used to say, it’s neither liberal nor party, it’s my political machine.

Ray taught me more about New York politics than any human being on Earth, but I’ve been very fortunate over the years.

RITHOLTZ:  Since you’re here discussing your book, let’s talk about books, what are some of your favorite books be they politics or what have you?

WILSON:  Well I’m going to say one of my favorite books is Cryptonomicon by Neil Stephenson.


WILSON:  Which is about money and the encryption and war, I’m a big fan of overly complicated stuff like that.  I was a classically educated guy so I read a lot of ancient history.

RITHOLTZ:  Give us a name.

WILSON:  Well, Livy and in Plutarch and Tacitus.

RITHOLTZ:  So you are  talking about real classic.

WILSON:  Yes, like actual, but for modern version — modern interpretation, Michael Grant is very good about a lot of stuff.  I read voraciously, so my house is way too full of books, so…

RITHOLTZ:  There are worse things to have filling up your house.

So what are you excited about right now?  What — I know that’s a silly question because I know what you’re excited about.

WILSON:  I’m excited about the fact that America is under a big stress test right now and I’m excited to watch how our resilience plays itself out this time.  I am really fundamentally optimistic about the country.  I think Trump is a terrible destructive horrible figure in our politics and our society, but I also think that there have been, you know, our immune system, it takes a while to kick in sometimes but it always does in the end, and I feel that starting to reshape where were going politically in the country.

And I’m also excited about the sort of you know modern elements of the bad sides of social media we see now but I think it’s also provided this new organizing tool and this new way of — for people to remediate themselves into effective political groups, so…

RITHOLTZ:  Tell us about the time you failed and what you learned from the experience?

WILSON:  Sure, I failed in 2016, I did everything I could to stop Donald Trump, I helped run Evan McMullins presidential campaign as an independent, we absolutely crashed and burned, it was horrifying.  What I learned was the two-party system is really strong, that tribal affinity is really strong and you have to bring a real A game to those things to break that mold.  And you learn more from the campaigns you lose than the campaigns you win.

RITHOLTZ:  Isn’t it always that way?

WILSON:  It is always that way.

RITHOLTZ:  You always will learn from failure.  What do you do for fun?  You mentioned cooking, what else do you do?

WILSON:  I hunt, I fly, I like to be out on the water.

RITHOLTZ:  You have a pilot’s license.

WILSON:  I do have a pilot’s license.

RITHOLTZ:  What do you fly?

WILSON:  Piper Archer.


WILSON:  So just a little thing but I get out as much as I can on the water which I love, I love my — I got a bunch of hunting dogs, German Shorthaired Pointers, and then and luckily, since I live in Florida, I love the chainsaw things because we have a lot of trees down after the big storms lately, so…

RITHOLTZ:  We came very close to getting a Gryphon German Shorthaired — they are just spectacular dogs.

WILSON:  German Shorthairs are an amazing dog, they are great hunting dogs in the field, they are great family dogs at home.

RITHOLTZ:  You just have to run them.

WILSON:  You do have to run them.

RITHOLTZ:  I have a Portuguese water dog.

WILSON:  I love them…


RITHOLTZ:  In the pool out on the boat out constantly.

WILSON:  Yes, yes, yes.

RITHOLTZ:  All right, so a millennial comes up to you and says I’m interested in a career and in political consulting, what sort of advice would you give them?

WILSON:  The first advice I would give them is go volunteer on a campaign to do the crappiest job you can find, drive, you know I started out with Connie Mack as an advance kid, as a driver. that’s how I started in this thing, I ended up meeting and getting to work for the president of — the future president United States because I had hustle, and you know, being willing to go out and do the scutwork and the crap jobs and the stuff that you don’t — you know, they get this one wrong impression from watching  television where there’s these 24 year olds in perfect suits in the White House being yelled senior officials, you got to go do the hard work and politics is one of those few things in this country where it doesn’t matter where you went to school, you got to go out and be in the field and bust your tail and you got to go do the things that — put the stupid yard signs and go deal with the cranky volunteers and go knock the doors.

You don’t get into this tribe of consulting unless you go and do those things and it’s all — it’s, there’s no shortcut to it.

RITHOLTZ:  Makes sense.  And our final question, what you know about the world of politics today you wish you knew 30 or so years ago?

WILSON:  People lie to pollsters all the time.

RITHOLTZ:  Really?


RITHOLTZ:  That is…

WILSON:  They lie to pollsters all the time.

RITHOLTZ:  That is not well understood by a lot of folks.

WILSON:  No, and it is clearer and clearer all the time how much they’re a bunch of damn liars.

RITHOLTZ:  Amazing.

WILSON:  I love it, I love trying to like get to the nut of a question with polling but you got to just factor that in these days.

RITHOLTZ:  Quite astonishing.  We have been speaking with Rick Wilson, he is the author of the “New York Times” bestseller “Everything Trump Touches Dies.”  If you enjoyed this conversation, well, look up an inch or down an inch on Apple iTunes and you could see any of our other let’s round it to the size of trumps inaugural address and call it 250 previous conversations over the past five years.

We love your comments, feedback, and suggestions, write to us at MIBPodcast@  You can check out my daily column on, follow me on Twitter @Ritholtz.

I would be remiss if I did not thank the crack staff that helps put these conversations together each week Michael Batnick is my head of research, Taylor Riggs is our booker/producer.  I’m Barry Ritholtz, you’ve been listening to Masters in Business on Bloomberg Radio.



Print Friendly, PDF & Email

Posted Under