Buttigieg and Warren conducted almost a controlled experiment in these two approaches during the final months of 2019. Perhaps surprisingly, it was the millennial candidate who went retro. Warren’s campaign leaned heavily on a modern, digital-first strategy early in the campaign, believing that the traditional, broad-brush medium of television wouldn’t be effective until later in the contest. Buttigieg invested early, consistently and heavily in television, believing it was the best messaging tool to help a relative unknown break through the pack.

But this is not just an argument between two candidates for president. It is also the latest brief in a disagreement that goes back more than a decade, between two Democratic messaging masterminds who are colleagues turned campaign rivals. Larry Grisolano, 55, is Buttigieg’s top media consultant and a veteran of Democratic presidential politics. Joe Rospars, an alum of Howard Dean’s 2004 campaign who is not yet 40, is Warren’s top strategist. The two men have sparred over how political candidates should balance spending on TV and digital since 2007, when they both worked for Barack Obama as he sought to become the first-ever African American president.

Considering the history between Rospars and Grisolano, a former Obama campaign staffer said, “It is not surprising that the two of them are now at war with each other again.”

Larry Grisolano | Julia Schmalz/Bloomberg via Getty Images

When David Axelrod began assembling a team for Obama’s first presidential campaign, Larry Grisolano was his first phone call. The two had known each other since the 1990s. Eventually, Grisolano oversaw all of what political professionals call “paid media”—advertising—for Obama’s 2008 campaign. Not long after his conversation with Axelrod, Grisolano brought 30 people into a conference room in Des Moines, where they sat, theater-style, with a large screen at the front and individual test dials in front of each of them. If you’ve seen a Frank Luntz focus group on cable news, you know the drill: They were to turn the dials varying degrees to the right to show how strongly they liked a particular scene, or to the left to register their distaste.

Images flashed of Obama, a young politician from a nearby Midwestern state starting with the letter “I.” Here he was, giving a speech at the Democratic National Convention to thunderous cheers. There he was in a black and white photo, helping people in Chicago register to vote. The dials started to move.

Then the video shifted to an interview with Harvard law professor Laurence Tribe, and the testers turned their dials hard to the right—the tracking line shot straight to the top. Democratic strategist Pete Giangreco, in the session at the time, pulled his head back in surprise. “I’m sitting there saying, ‘Who the fuck cares about some Harvard professor?’” Giangreco says, recalling the moment. “But then he delivered that line, that Obama could have taken all that knowledge, all that pedigree from Harvard and made a killing on Wall Street. But instead he decided to devote it to making people’s lives better.”

An ad featuring, of all people, Larry Tribe was produced, and it became one of the most memorable spots of Obama’s 2008 run for office. To Grisolano’s contemporaries, it’s part of the résumé that makes him the gold standard among Democratic TV admakers. Giangreco says the moment in the dial-testing room gave him goosebumps. People who have worked with Grisolano describe him as meticulous, a visionary, even a genius.

In Iowa, where caucusgoers are older, Grisolano firmly believes TV still has the greatest impact. “Television is viewed as inefficient because it is compared to television as it used to be,” he said. “But if you look at what your options are today, television remains the best vehicle to reach a lot of people in a short period of time. I believe with digital, when you have the luxury of time, it can sink in over time. But largely, if you look at how commercial advertisers use digital advertising, it’s almost exclusively for direct response.”

One Obama staffer, however, saw shortcomings in Grisolano’s strategy. Then just 25 years old, Rospars had cut his teeth in Democratic presidential politics on Dean’s 2004 campaign, and he was an insurgent believer in the power of new media. People’s media habits were changing. They were spending more time online. The campaign should find new ways to reach them, Rospars argued. “I remember Rospars thinking Larry was ancient in 2008, in that he was addicted to broadcast television and didn’t invest in digital,” says Jeff Link, who worked for Grisolano as Obama’s deputy paid media director. “He was always coming back asking, ‘Why aren’t we committing more to digital?”