Teaching the Presidency Through Character

Nathan Harden | November 15, 2026

(RealClearEducation) — When Harry Truman moved into the Oval Office, he cleared FDR’s things off the walls and hung two portraits: Andrew Jackson on one side, Franklin Roosevelt on the other. Ronald Reagan, on the other hand, asked for a portrait of Calvin Coolidge.

“You can tell a lot about a president by whose pictures are on the walls of the Oval Office,” David Brooks says in In Pursuit: Lessons of American Leadership, the new PBS documentary from Retro Report. “It’s like they have the dead whispering to them.” When it comes to the world’s biggest job, those who hold it have learned from those who preceded them.

That idea is the film’s case for a distinctive way to teach about the presidency. Students usually encounter the office in one of two ways: as a civics diagram of powers and checks, or as the subject of a partisan fight. In Pursuit treats the presidency as a long line of individual choices and asks former presidents to reflect on which choices taught them the most. George W. Bush writes about Washington’s humility, Barack Obama about Lincoln, Bill Clinton about Theodore Roosevelt. Chief Justice John Roberts writes about William Howard Taft.

The film also doesn’t shy away from presidential failings or controversies, from slavery at Mount Vernon to the Iraq War. For teachers who have learned to avoid presidential politics in class, it offers a way back into the subject through history, at enough of a distance that students can debate character and power without arguing about today’s politics.

Retro Report has produced classroom materials for middle and high school students related to the documentary. RealClearEducation asked David Olson, who leads Retro Report’s education work and has taught at the middle school, high school, and college levels, what teachers and students can take away from it.

For readers new to this project: what is In Pursuit, who is behind it, and how did Retro Report come to make a film from it for PBS for the 250th anniversary?

In Pursuit is a project of More Perfect, led by Colleen Shogan, John Bridgeland, and several others. Retro Report was privileged to partner with them to turn the project and its series of essays into a special for PBS. We thought the essay and podcast series was an amazing starting point for exploring presidential history and the lessons we can learn from presidents’ leadership.

Why look at American history through presidents and first ladies? What can students learn from this group that a broader history of the country might miss?

Presidents and first ladies are a natural place to turn when studying history and civics. This small group of individuals are probably the most recognizable people when we think about major historical events. What makes this project unique is that we tried specifically to draw lessons from their leadership. This film and the accompanying resources are about more than just “what happened.” They’re about what we can learn from people who faced intense challenges under a bright spotlight. Students gravitate to stories, so examining the character and choices of people making momentous, difficult decisions is really engaging for students, and for everyone!

The film argues that Article II says relatively little about the presidency, so much of the office was built from precedent, starting with Washington’s choice to step down. Most students meet the presidency through today’s partisan fights. How do you help them see the difference between what the Constitution requires and what is only custom?

From my own experience teaching middle school, high school, and college courses, the best place to start is with the Constitution. Not only does Article II provide a pretty limited list of powers, but the arguments in the Federalist Papers were meant to show that the president’s power would be limited. Students always find it fascinating that Madison, Hamilton, and others were convinced the legislative branch would be dominant, so it’s fun to have students analyze the president’s different roles and how those roles square with the Constitution. I also think it’s important for students to understand that our partisan fights about the executive branch are not new. That is the power of using history as a lens to examine the present.

The series puts a lot of weight on character, such as Washington’s humility, Grant’s restraint during the Johnson-Stanton fight, and Taft’s habit of asking where the Constitution gave him authority before he acted. Civics classes usually focus on structure and process. Can character be taught through history?

Absolutely. Examining character gives students the chance to see historical figures as real human beings. We aren’t governed by deities. We get, and choose, real people. Structure and process are essential to understanding how our government operates, but stories about real people making consequential decisions are what give that content life. Narratives and storytelling hook students and help them connect concepts to real-world applications. I’m not sure how you would teach character without history, so my hope is that this film and the classroom resources make life easier for teachers.

The film doesn’t hide its subjects’ failings. It mentions the enslaved people who worked Washington’s land, the “tentative” antislavery position that Obama attributes to Lincoln, and the Iraq War. How should teachers present presidents as flawed and still worth learning from, without sliding into hero worship or cynicism?

I believe in being honest with students, and I think it’s great when teachers can model this kind of analysis in their classrooms. Humans are flawed. They can do great things and make difficult decisions alongside serious flaws. Only 45 people have served as president, and they have been at the forefront of the most important decisions and actions in U.S. history, which makes them a natural starting point.

Several segments feature people who held power themselves: George W. Bush on Washington, Obama on Lincoln, Clinton on Theodore Roosevelt, and Chief Justice Roberts on Taft. What do students gain from hearing leaders explain which predecessors shaped them, and should teachers help students approach those perspectives critically?

This question connects well to learning to think like a historian and to building media literacy. When we hear from people like George W. Bush, Barack Obama, or Chief Justice Roberts, we want students to account for the perspective of the author or speaker. Having students examine how that perspective might inform a position is an excellent task, and I think it will lead to excellent questions from students as well. Teachers can ask students directly: How might Bill Clinton’s perspective differ from a historian’s when writing about Teddy Roosevelt? What different things might we learn depending on who is telling the story? These skills carry over to the rest of our study of history and civics.

The film raises the question of whether too much authority has piled up in one office. How can teachers take on those kinds of questions in a mixed classroom without it turning into an argument about the current president?

I hear regularly from teachers that discussing current events and political topics can be a minefield. That’s why a film like In Pursuit can help. Using history as a lens shows us that most of our political, social, and economic debates aren’t new. The debate over presidential power has been with us from the very beginning. It shaped the Articles of Confederation, the Constitution, and several amendments. My hope is that we’re making it easier for students to ask questions and think critically while tying their thinking back to historical examples and primary sources. That approach can help defuse partisan arguments, and it’s also good teaching.

The In Pursuit site lists educator resources by grade level, along with lesson packages developed with partners like iCivics and the Bill of Rights Institute. How do you hope teachers will use the film alongside those materials?

The Retro Report resources should be on that site soon as well. Along with the PBS special, we produced a handful of standalone short videos about first ladies, including Eleanor Roosevelt’s role as a human rights leader, Bess Truman’s efforts to preserve the White House, and Nellie Taft’s ambitions for her husband. As Presidents Day approaches, we will also release segments of the PBS special, accompanied by lessons and activities for middle and high school civics and U.S. history classes. My hope is that teachers explore the full collection from iCivics, the Bill of Rights Institute, and Retro Report. Across the organizations, we have grades 3-12 covered, with more to come. The full film is a great entry point for teachers starting a unit on the executive branch, and the individual segments fit well when teaching specific moments in history or the roles of the president.

This article was originally published by RealClearEducation and made available via RealClearWire.