I recently read Uncharted: How Trump Beat Biden, Harris, and the Odds in the Wildest Campaign in History by Chris Whipple, whom I consider one of the finest political journalists writing today.
Here are my key takeaways from Uncharted as a political consultant:
Lesson 1: You Can’t Win by Tiptoeing Around Your Opponent
During the primaries, Ron DeSantis didn’t really take on Donald Trump. As a challenger, you need to go on the offense. You can’t win by tiptoeing around your opponent. But what happened was actually the opposite. Behind the scenes, Trump’s team launched a concerted effort to define DeSantis, which would ultimately end his campaign before it ever started for good.
Lesson 2: Denial at a time of Crisis is Deadly
After the disastrous debate, Biden and his team were, by Whipple’s description, in denial. At a time of crisis, this is deadly, as crisis management rewards realism and speed. One cannot help but wonder what might have happened if the response of the Biden team had been more immediate, more aggressive, and more grounded in political reality.
Lesson 3: The Calling Pyramid
When Kamala Harris stepped in after Biden dropped out, she executed one critical move extremely well: the consolidation of her candidacy. Whipple recounts that within days, she made more than a hundred phone calls to opinion leaders and key figures in the Democratic Party. By doing so, she skillfully locked down the elites and prevented a process of intra-party fragmentation.
Lesson 4: Never Ever Again Be Swift-Boated
A weaker moment came when Trump’s team launched a barrage of negative advertising on Harris. A particularly effective one focused on Harris’ previous position supporting gender-affirming surgery paid for by taxpayers. According to Whipple, the Harris team tested various responses but ultimately chose to try and pivot away rather than to forcefully confront the attacks. From a tactical standpoint, that was a major mistake.
Lesson 5: Visuals Matter More Than Commentary
Trump’s campaign demonstrated an instinctive understanding of visual politics. They seized moments — even something like the “garbage truck” episode — and turned them into powerful imagery. It does not matter as much what commentators say on television. What matters is what voters see on television. Strong visuals cut through noise. They simplify narratives. They linger.
Lesson 6: Men Also Vote
Another strength of Trump’s operation was its outreach to low-propensity voters, many of them young men. At the time, much of the media hype focused on women and especially young women and single mothers. But men vote too — and their votes count exactly the same.
Lesson 7: Television Still Matters — A Lot
Whipple notes that in the final weeks Democrats were actually outspent on television because they devoted substantial resources to their ground game and get-out-the-vote operations. Ground operations are important, no doubt. But this confirmed something I have long argued: while television advertising is less dominant than it was 20 years ago, it remains the ace of political communication.
Lesson 8: You Must Be Change When the Status Quo Is Unpopular
On the most fundamental level, Harris’ problem was clear. The dissatisfaction with Biden was an albatross around her neck. She represented status quo at a time when that was very unpopular. At the beginning of her short campaign, she tried to represent change, and she could and should have pursued that route aggressively. But as the campaign went on, she increasingly represented the status quo and was ultimately rejected by the voters.
Whipple’s Uncharted reads like a case study in timing, denial, consolidation, messaging and strategic clarity and the power of visuals. For anyone who works in campaigns — or studies them — the lessons are neither abstract nor academic. They are practical, and they are unforgiving — I can highly recommend the read.