Daniella Diaz spent months as Elizabeth Warren’s shadow.
The CNN producer crisscrossed the country, following the presidential hopeful as she pressed the flesh in a middle school gymnasium in Muscatine, Iowa, or delivered a blistering rebuke of Donald Trump in a packed auditorium in Lebanon, N.H. Anywhere the candidate looked, while working a rope line, taking a debate stage, or posing for selfies with supporters, she’d be likely to find Diaz and her camera gazing back at her.
It’s a heady, grueling experience to be a campaign embed like Diaz. But it was one that took an unusual turn when the cameras were turned on Diaz herself.
“I never thought that I would be the story,” says Diaz. “My goal has always been to shed light on other people’s stories, but I just kept doing my job and focusing on accomplishing what I needed to accomplish in any given day.”
That job and those of several other women journalists who followed the dozens of Democratic candidates around from one grip-and-grin to another is at the heart of “On the Trail,” a new campaign documentary that premiered this month on HBO Max. The film also serves as the inaugural effort in what is shaping up to be a very important partnership between the new streaming service and its corporate cousin, CNN Films.
“We got some fantastic natural moments from these women, and you kind of fall in love with them because they’re not all household names,” says Amy Entelis, executive vice president for talent and content development for CNN Worldwide. “You get a sense of their daily lives and the sacrifices they make to get a story out. It’s fascinating and inspiring.”
“On the Trail” is the first of many collaborations between the two WarnerMedia divisions. HBO Max will premiere “Persona,” a deep dive into America’s obsession with personality testing. The pair will also team on “Generation Hustle,” a series about the things young people will do to achieve fame and fortune, from Oscar winner Alex Gibney; and “Heaven’s Gate,” a look at a cult movement that ended in mass suicide. CNN Films is also selling HBO Max streaming rights to movies that it plans to release theatrically, such as “Bourdain,” a look at Anthony Bourdain, the globe-trotting chef whose travel show aired on the news network. Focus Features plans to distribute the movie in cinemas.
HBO Max, which launched in May, is hungry for fresh, original content. CNN Films, which is in the business of producing buzzy documentaries, has plenty of that and a very particular need. Because it is housed inside CNN, a 24/7 news operation, the documentary filmmaker has only so many slots it can fill. Moreover, the Trump presidency has made it even harder to get space, with the news division devoting more and more time to the various controversies emanating from the Oval Office and earning bigger ratings in the process. As it stands, CNN Films makes between four to six features a year, ranging from “RBG” to “Three Identical Strangers,” and produces 9-12 multipart series.
“There was a sense that we can always do better, but we can’t necessarily do more,” says Entelis. “So I started looking around and thinking how do we grow this?”
After Sarah Aubrey was appointed as head of original programming for HBO Max in July 2019, Entelis moved fast.
“Amy was the third person on my phone sheet after my mother and my former agent called,” says Aubrey “She called before it was even announced internally. What I love about Amy is literally from minute one she realized that this was going to be an opportunity for both of us. I’d get a best-in-class producer, and she’d be able to program some content that either there wasn’t space for on CNN or that didn’t work for that audience and demographic.”
For HBO Max, CNN Films filled an important need. Unlike Disney Plus, which is owned by the same conglomerate as NatGeo, HBO Max had no in-house provider of unscripted content. And Aubrey says she has found that that kind of content performs remarkably well with streaming customers.
“I’m learning every day about what’s right for the platform,” says Entelis. “We have certain strengths that we can add to certain projects, but we don’t do reality shows or something like that. We stay in our lane, but there are certain things that we can do that no one else can.”
Before she reached out to Aubrey, Entelis had come to see CNN Films as having arrived at a pivotal transition moment. When she launched the division in 2012, she says there were many skeptics inside the company. CNN had not invested heavily in the documentary space; its bread-and-butter was global, breaking news. Initially, the idea had been to buy more completed films, but Entelis quickly realized that the prices for these were often exorbitant — with sales agents asking top dollar for the movies that made a stir at Sundance and other festivals.
“We kept getting outbid,” Entelis says.
So she and her team turned their attention to making their films in-house and found success with many of their initial projects. “Three Identical Strangers,” a story of triplets separated at birth, was a box office hit when it opened in 2018, grossing more than $13 million globally (a huge number for a doc). “RBG,” an extensive look at Supreme Court Justice Ruth Bader Ginsburg, earned a hefty $14 million worldwide and scored an Oscar nomination for best documentary. Other films — such as “Love Gilda,” which examines the tumultuous career of comedian Gilda Radner, and “John Lewis: Good Trouble,” a look at the life of the civil rights pioneer and congressman — were critical successes. These films air on CNN after having a theatrical run.
“Right around the time that HBO Max was announced, we were sort of just coming to our maturity,” Entelis says. “We had been a scrappy underdog in the beginning, and nobody understood what we were up to. Now we were getting noticed, and we needed to find fresh collaborators.” In the case of “On the Trail,” the project came about after Entelis realized that many of the CNN journalists who were embedding with the campaigns were women, many of them in their 20s. She started to think that they would be an important prism through which to examine the 2020 presidential election. Aubrey, a political junkie herself, agreed that it could be the makings of an interesting inaugural project.
“We really wanted to do something that was behind the scenes of the election but would not be the kind of thing you would find on CNN proper,” says Aubrey. “We didn’t want something that was strictly newsy, but I loved the idea of looking at how a story gets told on the trail and also the toll that the trail takes on the journalists themselves.”
“On the Trail” went through several permutations before the partners hit on a winning formula. Initially, Entelis wanted to do a multipart series, one that would air on HBO Max in roughly real time, but that proved to be unrealistic given the sheer number of candidates and the fast-changing nature of the story, not to mention that the primary had essentially wrapped up by the time HBO Max launched. Instead, they settled on a two-hour film that roughly follows the course of the primary itself. CNN journalists were told they didn’t have to participate if they didn’t want to, but most of the reporters said they enjoyed the experience and welcomed the opportunity to give friends and families insight into the job that kept them on the road for months.
“I’m hoping this ends all the questions about what it is exactly that I do,” says Jasmine Wright, who traveled with the Kamala Harris and Amy Klobuchar campaigns. “I definitely don’t think people know what the word ‘embed’ means, and this film shows how rigorous the job is and how dedicated you have to be.”
Even though some of the footage for “On the Trail” was shot only last spring, it seems like a time capsule from a different era. The crowded events and rallies that these correspondents witness and report on are a thing of the past, made impossible by the coronavirus pandemic. But Aubrey thinks that people are burned out by the constant coverage of COVID-19 and are eager to take a more reflective look at how we got to this moment.
“We’re releasing it at a time where we’re going to start focusing very intently on who is going to win this election,” says Aubrey. “But what’s fascinating about the piece is you see markers of what is coming. It’s a ticking clock, and there’s a train wreck at the end of this that’s going to bring the entire world to a screeching halt.”
As for CNN Films, the pandemic has complicated its efforts to keep making documentaries. However, the company is continuing to greenlight projects. It has also started doing social-distanced interviews with subjects and is developing ways of working during the pandemic.
“We don’t want to lose our momentum,” Entelis says. “There’s lots of great projects out there that we’re committed to getting completed. We all have to face the world that we’re in and we want to keep making films, so we have no choice but to go forward with great optimism.”