Sad!

These three campaign gurus for Jeb Bush, Ted Cruz and Marco Rubio
have had some time to reflect on their loss to The Donald.
And do they ever have stories to tell.

Interview By Sam Stein
Photos By Matt Roth

Sad!

These three campaign gurus for Jeb Bush, Ted Cruz and Marco Rubio
have had some time to reflect on their loss to The Donald. And do they ever have stories to tell.

Interview By Sam Stein
Photos By Matt Roth

It's been roughly 40 days since Donald Trump became the presumptive presidential nominee of the Republican Party, and the mere fact of it hasn't come to feel any less weird, or any less scary. It also means that the three people I had coffee and pastries with last Wednesday morning—Danny Diaz (Jeb Bush's campaign manager), Jeff Roe (Ted Cruz's campaign manager) and Alex Conant (Marco Rubio's communications director)—have been able to process what the hell happened.

Well-compensated, highly intelligent and very publicly defeated, each one of them is still angry, both at Trump and at the media. Each one of them has theories about how we got to this very disconcerting place in American political history. And not one of them is prepared to vote for Trump.

The stories they told me over a 90-minute conversation at a bar called Black Jack in Washington DC provided an entirely different view of the campaign and of elite Republican thinking. They spoke with unusual candor about which strategies they pushed that they now regret, how they believe network executives conspired against their candidates, what a disaster the Republican convention will be and why a Hillary Clinton blowout may be upon us. This is what it’s like to lose to Donald Trump.This interview has been edited and condensed for clarity.

This interview has been edited and condensed for clarity.

When you enter an election, you have a carefully laid plan about how you’re going to win it. At what point in the cycle did you realize that plan was meaningless?

Danny Diaz (Jeb Bush's campaign manager)
A D.C. fixture whose biggest successes have been for moderate Republicans. He helped elect Mark Kirk to the Senate in Illinois and Susana Martinez to the governor's mansion in New Mexico.

I appreciate your starting with me. [laughs] Right after Labor Day, we understood that it was going to be a really, really difficult race for us, despite the advantages that we had. It was persistent in the survey work just the level of unhappiness, anger and disaffection among voters.

A D.C. fixture whose biggest successes have been for moderate Republicans. He helped elect Mark Kirk to the Senate in Illinois and Susana Martinez to the governor's mansion in New Mexico.
Jeff Roe (Ted Cruz's campaign manger)
He is often described as one of the sharpest minds in Republican politics, the next Karl Rove.

Labor Day was about the time we knew, too.

He is often described as one of the sharpest minds in Republican politics, the next Karl Rove.

Really? That seems early.

Roe

So we did 5,000 calls a night from the day we got in the race to the day we got out. We had a continual analytic program. And you could tell from early on that Trump had a floor. He was always going to have 25 to 30 percent of liberal-to-moderates, he was going to have 25 to 30 percent of somewhat conservatives, he was going to have 25 to 30 percent of very conservatives.

Alex, what about for you?

Alex Conant (Marco Rubio's communications director)
He's a well-regarded communications hand who cut his teeth in the George W. Bush administration before heading over to the RNC. He also ran press for Tim Pawlenty in 2012.

Well, we were a lot later than that. We knew that Trump was going to be strong going into the holidays, but it wasn't until after he beat us in Nevada that we felt he was more likely than not to be the nominee.

He's a well-regarded communications hand who cut his teeth in the George W. Bush administration before heading over to the RNC. He also ran press for Tim Pawlenty in 2012.

Let’s go back to the moment Trump descended his beautiful gilded escalator at Trump Towers to announce his candidacy. Did you honestly recognize him as a threat?

Conant

I was skeptical. Like a lot of people, I didn’t even know if he would qualify for the first debate. I didn’t know if he would be willing to file the FEC financial disclosures, or if the networks would take him seriously enough to allow him to be on the stage.

I had the editor of a major news outlet tell us that for every candidate who enters the race, they do five stories, including a deep dive on their background and a fact-check of their speech. But they weren’t doing that for Trump because they didn’t take him seriously. They just viewed it as publicity. And that was how I thought about his candidacy as he came down the escalator.

Diaz

If you took a cursory look at his record, the positions and stances he had taken, and lined those up against where conservative voters are, it was hard to see how those two lines connected at the outset.

And thus began the fall. (Getty)

Jeff, what was your polling telling you at the very beginning?

Roe

We do our polling a little bit different. We always had a continual, rotating “consider score.”A consider score measures whether a respondent will consider a candidate for the office they are seeking. When Trump got into the race, I think he was at a 28/58 favorable/unfavorable rating. And he was earning about 3 or 4 percent in the overall ballot. But his consider score matched his favorable rating, which never happens. Your consider score should be in between your favorable and your ballot.Ben Carson, on the other hand, had a huge favorable number, but few people seriously considered voting for him for president. So, out of the gate, the race became about him or not him.

A consider score measures whether a respondent will consider a candidate for the office they are seeking.Ben Carson, on the other hand, had a huge favorable number, but few people seriously considered voting for him for president.

There were a bunch of times when people were like, “Well, this is going to do him in.” Like when he said John McCain wasn’t a war hero, or the Megyn Kelly menstruating comment, or making fun of a disabled reporter. Which one made you say, “This guy is smoked”?

Roe

All of the above. There was a time when you wondered if the bug was going to meet the windshield or not. But everything was brand-consistent. His brand was being politically incorrect: He’s saying everything that you’ve always wanted to say. You might not like it, but he’s speaking for you. He's the billionaire blue-collar guy. That’s why this Mexican judge thing is different. That's him looking out for himself, instead of him looking out for you.

Diaz

What’s different now is the electorate. He’s playing to a much broader field of people than he was in the primaries.

Let’s be nice to each other for a minute. What was a strategic decision that a rival campaign made that impressed you?

Roe

Bush’s manhandling of Romney was pretty impressive. I think Mitt was a big question mark at that point in the race.Romney, the 2012 Republican nominee, was flirting with the idea of entering the race in January 2015 but ultimately decided against it. He would have walked in with a ton of credibility, a ton of dough, a ton of institutional support, and really swamped that lane. It was interesting to watch how Bush was making donors saddle up. It was very clearly aimed at one dude.

Romney, the 2012 Republican nominee, was flirting with the idea of entering the race in January 2015 but ultimately decided against it.
Conant

I would agree. I thought the early days with Jeb’s campaign, when he was able to lock down the Florida establishment and the Florida donor base—not only did that continue to be a long-term problem for us, it was very effectively done. And then I think the Cruz campaign showed an amazing amount of discipline through the summer. Partnering with Trump at the Iran rally was a really smart move. Our campaign manager said last fall that he thought the Cruz campaign was the best-run campaign in the race, and I think that held throughout.

Alex, what would you say was the low point of your campaign?

Conant

The New Hampshire debate was our low point.It was a disaster. Rubio had just performed well in Iowa, and it seemed as if he was about to consolidate elite support. But on stage, Chris Christie mercilessly mocked him for being robotic. Rubio responded by assuming many of the characteristics of a non-carbon-based life form.

It was a disaster. Rubio had just performed well in Iowa, and it seemed as if he was about to consolidate elite support. But on stage, Chris Christie mercilessly mocked him for being robotic. Rubio responded by assuming many of the characteristics of a non-carbon-based life form.

I thought you might say that one. What was it like being backstage for a moment like that?

Conant

In the moment, you know it’s not good, but you don’t know how bad it’s going to be. You're certain it’s not great, but the instant metrics that we had in terms of the fundraising, what the Google analytics were saying about how people thought Marco did were all encouraging. But the media narrative coming out was just devastating.

The media would be wise to come out and tell the truth, which is: We make business decisions, and the reality is that this guy sells magazines and ads. Danny Diaz

So you’re in a competing campaign, and you’re watching Chris Christie essentially put the shiv into Rubio on the stage. Does any part of you feel sympathy for him?

Roe

No, no, no. Maybe afterward. But no. It’s an aggressive contest.

We all sit within 20 feet of each other in different rooms in these awful debate locations. So you can hear other campaigns react. But you don’t hear everybody cheering when somebody else screws up. You hear cheering from other rooms when their guy does well.

Diaz

What's amazing is that you can talk about New Hampshire and Rubio, you can talk about Boulder and Jeb.Bush tanked badly at this debate. Attempting to mock Rubio for not showing up for work in the Senate, he ended up being widely criticized for his desperation. I mean, Trump had a moment like that in every other debate. But everyone was kind of like, “That's Trump,” and moved on.

Bush tanked badly at this debate. Attempting to mock Rubio for not showing up for work in the Senate, he ended up being widely criticized for his desperation.
Rubio hurt this kid a lot more than he hurt Trump.

Which rival candidate pissed off your campaign the most?

Diaz

I'm glad you started on the other side of the table this time.

Conant

I'm struggling. I mean, I don't fault Chris Christie for trying to beat Marco.

I'm not asking who you fault. I'm saying, who pissed you off?

Conant

Honestly, probably the Jeb campaign for spending as much as they spent against us, which I realize was more of the super PAC than Danny.

Let it out, man.

Diaz

It will make you feel good.

Conant

There is no question that having tens of millions of dollars spent against you in Iowa…

...Sucks?

Conant

Yes, that had an impact on the outcome of the election.

Diaz

I’m going to be candid with you. I don't take it personally. It’s business.

You're gonna sit here and tell me that Trump calling your candidate "low-energy" for months on end didn't piss you off?

Diaz

Well, hold on. We’re running a race for the presidency of the United States. I have every expectation that anything and everything on the table will be used to try and achieve a desired outcome. With that said, quite obviously Donald Trump’s personal slurs against Jeb and against his family were and remain totally and completely outside the bounds of what is appropriate in discourse. And I feel like, looking back now, he was appealing to a certain kind of element within the electorate. He’s playing the same card now, and it doesn't seem to be working to his benefit. The dynamics are entirely different.

Roe

I agree with everything Diaz said. Our campaign office is 13,000 square feet. You sign that lease the month before you announce. That’s $30,000 a month in overheard right out of the gate. You’ve got salaries stacking up. There’s a whole culture that comes with that. And so ranting and raving about this candidate or that candidate can really get a campaign sideways. It will obviously give permission to the junior and younger staffers to do things that will not be beneficial to your campaign.

But when John Kasich...

Roe

So I have an answer. I mean I’m upset at, routinely, all of the other candidates. But in reverse order: I do not know why John Kasich did not get out after Wisconsin, I don’t know why Marco didn’t get out after March 1, I don’t know why Ben Carson didn’t get out after Iowa. Actually, I was sad, more than mad, watching him be used by other campaigns as a wedge. Here was someone, who is by all accounts a great man, being completely manipulated.Roe was referring to how other campaigns piled on Cruz after his campaign spread word that Carson was dropping out of the race during the Iowa caucus, which was not true. Other campaigns, he felt, used Carson’s anger over the episode to paint Cruz as a liar.

Roe was referring to how other campaigns piled on Cruz after his campaign spread word that Carson was dropping out of the race during the Iowa caucus, which was not true. Other campaigns, he felt, used Carson’s anger over the episode to paint Cruz as a liar.

Watching John Kasich stuff his face instead of campaigning while siphoning off votes must have been frustrating.

Roe

Two things we measure all the time are media share and small-dollar fundraising. That’s what I spent ungodly amounts of hours on that I’ll never get back. But the pie and the eating and all that, that actually got him media share. He would get a half-day or he would get a quarter-to-a-half-day on that.TV days are split into four parts: early morning through 10 a.m., 10 a.m. through 2 p.m., 2 p.m. through 6 p.m., 6 p.m. through 10 p.m. Controlling those parts is essential to the success of a presidential campaign. It’s been the number one indicator for about 50 years.

TV days are split into four parts: early morning through 10 a.m., 10 a.m. through 2 p.m., 2 p.m. through 6 p.m., 6 p.m. through 10 p.m. Controlling those parts is essential to the success of a presidential campaign. It’s been the number one indicator for about 50 years.
Kasich: Nom nom nom, but not the nominee.

That’s a great campaign tactic! Just eat everything in sight…

Roe

A lot of people said that he should’ve gotten out, which is why I wish [his campaign manager, John] Weaver was here. It’d be nice to have him on the record. I mean, he won Ohio and they did confetti cannons. I get it. Ohio’s a big state. But then what state was he waiting on after that?

Isn’t the issue that there was a broader collective action problem among the non-Trump campaigns? Everyone wanted to be the last guy standing against him.

Roe

I think so. Our strategy required us to be head-to-head against him. And when your strategy requires somebody else doing something, that’s a pretty weak strategy.

Was there any backchannel communication to team up against Trump?

Diaz

Look, there’s always backchannel communication. But I think it would’ve taken more than one or two campaigns. I think the campaigns would’ve all needed to come together to say, “Hey, there’s a line in the sand here that’s been drawn, and we need to come together to vote someone off the island.”

Conant

In a typical election cycle you wouldn’t need all the campaigns to make that agreement. It would just be recognized by all of them that Trump is a huge threat, not just to the collective but to each campaign, and they would all target him in their own way and put an immense amount of pressure on him and his team. And that just never happened. He got a free pass from most of the other campaigns.

Was there a decision you wish you could totally do over?

Roe

Hundreds, right?

Diaz

Yeah.

Roe

We’re in Chicago, speaking at some big-donor Republican dinner, a real establishment crowd. It’s the Friday night before the March 15 primaries.March 15 was one of the most important days of the cycle, with Florida, Illinois, North Carolina, Missouri and Ohio all voting. And as Ted is speaking, these riots happen—well, "riots" is too strong. Let’s say Trump had a big disruption where they had to cancel the rally and there are fights and bottles being thrown and police cars being stomped on and all that stuff. And we’re thinking, “Well, this is probably going to help Trump.”About 30 minutes later, Roe told me he thought Trump tried to gin up the riots by holding a rally at the “racially diverse” Chicago campus of the University of Illinois the Friday before the election: “That’s no accident.”

So we were tied with him in Missouri and tied in North Carolina—and we had a decision to make about where we were going to go Sunday and Monday. We were already booked to go to North Carolina on Sunday, but do we stay in Illinois, where we thought we could pick up about 20 delegates in the outskirts of Chicago, or do we go to Missouri? We thought this could be the time to consolidate, to make it just us and Trump. So we spent Sunday night and all day Monday in Illinois. And we lost Missouri by 1,700 votes, and we lost North Carolina by 2,000 or 3,000, and we didn’t pick up any of the delegates. In Chicago, we went from down 4 percent to down 11.

I mean, in retrospect, no shit the protests were going to help him. And so that was an awful decision, which I solely made. It was a 40-delegate swing.

March 15 was one of the most important days of the cycle, with Florida, Illinois, North Carolina, Missouri and Ohio all voting.About 30 minutes later, Roe told me he thought Trump tried to gin up the riots by holding a rally at the “racially diverse” Chicago campus of the University of Illinois the Friday before the election: “That’s no accident.”

Alex, do you wish Rubio hadn’t mocked Trump for his skin color and penis size and all that?

Conant

I don’t know if that had an impact on the outcome of the race, but Marco himself has said that he regretted doing that.

So why do it?

Conant

The strategic reason to engage on that level was that we needed the race to become Marco versus Trump. And it worked to a certain degree. The media coverage coming out of the Houston debate and through that weekend was Marco-dominated in a way it hadn’t been the entire campaign, in some ways very positively.

Was it a unanimous campaign decision to do that?

Conant

Yeah. I mean, look, Marco said that he regretted doing it, so I don’t have too much to say on it beyond that.

Roe

Still on point, I love that!

I know, I thought you were going to be candid. We gave you coffee.

Roe

Well, you can tell who one of his big retainer clients is.Just two days before this conversation, Conant had opened a consulting firm with fellow Rubio alum Terry Sullivan.

Just two days before this conversation, Conant had opened a consulting firm with fellow Rubio alum Terry Sullivan.

What were you thinking when you were watching that?

Roe

Oh, we had an instant conference call to see if we should do the same thing: Get in the conversation.

And?

Roe

It was widely panned from our side. It was about media share, and they were soaking it up.

How quickly after your campaigns fizzled did you send your resume to the Trump people?

Diaz

I will be very candid. I have never spoken with anyone associated with the Trump campaign.

That was a facetious question.

Diaz

I understand. That was a less-than-facetious answer.

How about someone like Alex Castellanos? Here’s a political operative who spent the last year criticizing Trump, and he just took a job running one of the Trump super PACs. What should people make of a move like that?

Diaz

We’re in politics. Nothing is surprising.

Not surprising at all?

Diaz

Nope.

Conant

After the last six months, nothing surprises me.

What does that say about the state of the Republican Party then?

Diaz

I watch the shows and folks go on and they’re like, “Republican politics has changed forever. This has undone everything that has happened over the last however many decades or generations.” But I think we’re getting too far ahead of ourselves. This is a unique person, and the timing worked incredibly in his favor.

Do you think he poses a threat to the country in a way other candidates haven’t?

Roe

Everybody I talk to says we know what Hillary will do as president, but we’re not sure what Trump will do. I don’t know the answer to that yet.

He’s clearly broken a lot of norms. He can seem dirtier than we’re used to.

Roe

I don’t know if it’s dirty or not. Some of it’s OK. We were getting to be kind of pansies in politics. People used to shoot each other on the Senate floor, you know.

That happened like once or twice.

Roe

Politics used to be more anonymous. Now at least the chalk outline has a signature next to it.

It's got a Twitter stamp on it.

Conant

So, after Marco dropped out, I was invited by the State Department to do a bipartisan speaking tour in Australia. And the number one question I got from Australian officials was, “If he’s elected president, what happens to the U.S.-Australian relationship?” And my answer was always, “Look, our relationship with an ally like Australia is much bigger than any one individual.” And I sort of think the same about our country here. He's just one person. And no matter how bad you think he might be, our country is stronger. We’ve had bad presidents in the past.

That seems a bit Pollyanna-ish to me. You can easily envision a case where the Australian prime minister says something that Trump takes personally, and then he decides to cut off trade with them.

Roe

The rigors of democracy check this. If he’s going after a judge in California and we’re all blowing up like this, then imagine if he starts going after an ally.

But the Republican mantra about Obama has been that this guy is an out-of-control executive, doing unconstitutional things. How can you then turn around and say, “You know, the system will restrain Trump”?

Roe

Because Republicans control themselves. We police ourselves better.

OK, let’s play a little game here. Let’s say you have decided to become Democrats, and you have a chance to sit down with Robby Mook, who’s running the Clinton campaign. What advice do you give him about how to handle Trump?

Roe

I don’t want to offer advice to Robby Mook! This game we’re playing right now is how we get kicked out of the Republican Party.

Let’s play a different game then. Let’s say you get to take over a major newspaper…

Roe

OK, now we can dance. But we still have to become Democrats, same thing.

You are now Arianna Huffington or Marty Baron. You choose. And you have an investigative unit that you can assign to do a story that’s Trump- or campaign-related. What’s the story you do?

Diaz

Foreign business abroad for both candidates and how it will affect their policies oriented around major, major geopolitical issues.

Roe

Donald is one of the best players of the inside game, which was always the irony that we could never quite get over. What kind of deals does he cut? Those types of things. For the Clintons, I wouldn’t just look into the Foundation, which is the easiest piece of this pie to put together. The money her family made when she was secretary of state is incredible. I mean, that would put most people in jail.

We were getting to be kind of pansies in politics. People used to shoot each other on the Senate floor, you know. Jeff Roe
Conant

Yeah, I would follow the money for both of them. I think the most success the media has had pursuing a story against Trump has been following the veterans' money.

Roe

And it didn’t start until everybody was out.

Diaz

Right. Once you hit that 1,237 delegate number, you know what’s going to happen. The assignment of stories and the stack of hits that come against you as a Republican nominee.

You thought the media was holding off on Trump during the primary?

Roe

I believe that there were financial decisions made in media suites on who they wanted to have as a nominee and what they would do to him after he became a nominee. I don’t think all of this is accidental. I really don’t.

Diaz

It’s too uniform.

You’re right–we have a big media mogul meeting after this…

Roe

This judge situation? This story in November would’ve been, “Oh, this is just Trump.”

Conant

He tweeted the same thing [about the judge] in early March.

Diaz

The media would be wise to come out and tell the truth, which is: We make business decisions, and the reality is that this guy sells magazines and ads.

Roe

After Wisconsin, we had won four states in a row. We were having a moment. So we wrote a 13-minute speech, and it was one of our best speeches. We actually got the framing right, we got the look right. And 7 minutes and 11 seconds in, Fox News cuts away from our speech to a segment that shows how Donald can still win the nomination before June 7. That’s what they cut to. That’s a stunning thing, that’s a major political development. And those kind of decisions are not made by the beat reporters.

Diaz

Let me raise another one. George W. Bush had not campaigned in more than a decade. He goes out into Charleston, South Carolina, for Jeb Bush, and most of the cables did not carry it live. You have the former president of the United States, and how many stories have been written about him being a private kind of citizen, and if Donald Trump had given a speech on whatever, they all would’ve carried it live.

One thing about the coverage is that Trump was willing to go places that other candidates would never go. For instance, linking Cruz’s dad to the JFK assassination.

Roe

Oh, he didn’t know that for sure! He was just throwing it out there!

Do you think the media legitimized that kind of craziness by airing it at all?

Roe

I mean, he essentially runs the National Enquirer. So that was the way they would do their kind of dumping ground. But it’s tough. It's hard for the press to cover the press.

Who does Trump end up picking as a running mate? Dennis Rodman? The ShamWow guy?

Conant

I stopped trying to predict Donald Trump a long time ago. But, selfishly, I think he should pick somebody I agree with on policy. The future of our party belongs to next-generation conservatives who believe in reforms like the ones Paul Ryan often mentions. Someone like that would be great. But I have low expectations.

Roe

It seems like he's going to pick Newt [Gingrich]. I would’ve thought Newt took himself off the list after he criticized the judge thing, but they made up quickly, and it sounds like he respects him in a way, too.

On the flip side, who do you not want Hillary Clinton to pick as her VP?

Diaz

Elizabeth Warren.

You think Elizabeth Warren would be problematic for the Republican ticket?

Diaz

I, Danny Diaz, would not want see Elizabeth Warren as vice president of the United States of America. It would be an incredibly liberal ticket, and a ticket that would be incredibly damaging to America’s economy.

Left: The rictus grins of two dear friends. Right: To Newt or not to Newt? (Getty)

All right, you’re dodging the question. What about you, Jeff? Which VP candidate gives Hillary the best chance of winning?

Roe

I believe in base elections, and I believe in turnout. I believe that this election will be condensed into seven to 10 states and the actual number of people who still need to make up their mind is very small. We chase these people relentlessly. In actuality, though, if you’re trying to get another 10,000 votes in Loudoun County, Virginia, I think you can find those 10,000 votes more easily with people who already believe in you but aren’t likely to vote than you are by getting undecideds to vote for you. So I fear Democrats running a base campaign, directed toward liberals, maximizing that vote, and electing a devastating ticket. But if her philosophy is based on capturing the ever-shrinking middle, then she should do Tim Kaine.Current senator and former governor of Virginia. White guy with good foreign policy credentials. Safe as can be.

Current senator and former governor of Virginia. White guy with good foreign policy credentials. Safe as can be.
Conant

It depends on where the race is in mid-July. If it looks like it is going to be a close race, then a senator from Virginia or Ohio is probably the safest, smartest move to make. If she continues to have trouble uniting her base, I would fully expect her to look to someone like Warren. But if we are going into mid-July and Trump’s candidacy has imploded, or if he’s down by double digits, I would not be shocked if she went big and picked [former Secretary of Defense] Bob Gates or somebody like that, who could turn it into a real blowout in November. She would have to have tons of confidence that her base wouldn’t go anywhere. But a Clinton-Gates ticket would be very attractive to a lot of moderate Republican voters.

He hasn’t earned my vote yet. I’m not voting for Hillary. But he hasn't earned my vote. Alex Conant

Let’s talk about the Republican convention in Cleveland. Is it going to be chaos?

Conant

If I was at the RNC today, my concern would be twofold. One…

Do you have enough riot gear?

Conant

Right. I worry there’s going to be massive demonstrations in the streets like we haven’t seen at a convention since Chicago [in 1968]. If nothing else, that will distract from the candidate’s message. Two, I’m sure the media will focus an inordinate amount of attention on who is not on the stage. Where are the Bushes, where is Mitt Romney, where is Condi Rice?

So the two storylines coming out of Cleveland could potentially be demonstrations and splintered party, neither of which is helpful for Trump. And then in Philadelphia the next week, I think it's going to be the opposite. You'll have a party unified and the focus very much on the historic nature of her candidacy, which does not bode well for us going into the fall.

Roe

I think there will be riots in Cleveland because there are paid political protesters that the Democrats have.

You just made the case that it would work to Trump’s favor to have riots—why would Democrats pay them?

Roe

Maybe because they’re uncontrolled. Look, if you want a protest and you’re a Republican, you need about a month and a highly organized plan to get people to come out at 10:30 on a Tuesday. But if you’re a Democrat…

You start a Facebook page…

Roe

No, you call SEIU and you call AFSCME and you call the Teachers’ Union and you’ve got a protest in 15 minutes. I think the Democrats have a chance to overreach and really coalesce the party in a way Trump himself could not do.

What’s your level of confidence in a Trump victory in the fall?

Diaz

The reality is that we start with a very difficult map. I worked on the '04 campaign and that campaign carried Virginia, it carried Colorado, carried Nevada, New Mexico, it carried a lot of these swing states that are now moving in the opposite direction. As a Republican, we should start from the perspective of understanding that it’s a very heavy lift to begin with.

Roe

There are 120 days until early voting, 153 days until Election Day. The ground game—a good organization—gets you anywhere between 2.5 and 5.5 points, and if he’s giving all that away, that’s a problem. But I think he can win. I can see a Trump victory. I can see a Clinton blowout. And I think we’ll end up somewhere between.

What is almost assured is how lonely he will be in victory. Good luck if you’re a Senate Republican in a swing state anticipating turnout shifts. Those Senate campaigns have 10 to 15 people on staff. They've got a budget of $20 million, of which $15 million has to be direct voter contact. Super PACs aren’t equipped to do this kind of stuff.

And Trump’s whole idea is to bring in voters who have never voted.

Roe

Right, that’s his theory of the case: Take the people who typically don’t vote, who stand with you ideologically, and walk them into participation. That’s unpredictable in its own right. Usually you’ll have somewhere between a 2.5 to 4 percent drop-off anyway from the presidential vote to the down-ticket races. Now, imagine that along with a voter turnout problem or people coming out to vote for Trump but then voting for the Democrat for Senate or House. That is a very real possibility.

How do you think Hillary’s focus on being a woman and running a historic campaign will work against Trump's misogyny?

Roe

Jeez. Wow.

Diaz

That’s loaded.

Conant

Look, I think what we saw last nightThis was the morning after the California and New Jersey primaries, when Clinton picked up enough delegates to become the presumptive nominee. She focused heavily on being the first female candidate of a major political party. is what we're going to see from the Clinton campaign every day from now until November. Which is, they're going to make this election a referendum on whether or not you want a woman in the White House. Not whether or not you want Hillary Clinton in the White House. I think that’s her only message.

This was the morning after the California and New Jersey primaries, when Clinton picked up enough delegates to become the presumptive nominee. She focused heavily on being the first female candidate of a major political party.

Do you think it plays?

Conant

It’s better than asking people to vote for Hillary.

Roe

That is the thing that we haven’t spent much time on: what a complete and utter train wreck she is. They’re going to have to rely heavily on the no-to-Trump vote rather than the yes-to-Hillary vote. I mean, anybody would’ve beaten her in the primary besides a 74-year-old socialist.

Lincoln Chafee?

Roe

In a head-to-head, I think he would have won!

So, final question: It’s November, are you voting for Trump?

Conant

I don't know. He hasn’t earned my vote yet. I’m not voting for Hillary. But he hasn't earned my vote.

Diaz

Election Day is November 8.

Credits

Interview - Sam Stein
Sam is the senior politics editor of The Huffington Post.
Photos - Matt Roth
Matt is an editorial and commercial photographer based in Baltimore.
Development & Design - Gladeye
Gladeye is a New Zealand-based digital design agency.
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