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Yes We (Still) Can

10 min

Politics in the Age of Obama, Trump, and Twitter

Introduction

Narrator: Imagine standing in the West Wing of the White House on one of the final days of Barack Obama’s presidency. You’re there to conduct a final interview with the president, a moment that should feel like a triumphant capstone to eight years of history. But the atmosphere is heavy, somber, and surreal. Because just days later, the keys to this building will be handed over to Donald Trump. This was the disorienting reality for Daniel Pfeiffer, a long-time Obama staffer. The victory he had worked for felt like it was dissolving into what he called his "worst nightmare." How could a presidency built on hope and change be followed by a movement that seemed to reject its very foundations? This question is the driving force behind Pfeiffer’s book, Yes We (Still) Can: Politics in the Age of Obama, Trump, and Twitter, which offers a behind-the-scenes analysis of how the political and media landscape was fundamentally, and perhaps irrevocably, transformed.

The Startup Campaign That Rewrote the Rules

Key Insight 1

Narrator: The 2008 Obama campaign wasn’t just a political operation; it was, as Obama himself later called it, one of the "greatest start-ups in history." According to Pfeiffer, this wasn't a choice but a necessity. Facing the formidable Clinton machine, Obama’s team couldn't rely on the traditional Democratic playbook. Instead, they had to build something entirely new, grounded in five core building blocks.

First was attitude. Obama was comfortable with the idea of losing, which gave the campaign a fearless, risk-taking ethos. Second was scaling. The campaign exploded with grassroots enthusiasm, forcing the team to manage massive growth with limited resources. Pfeiffer recalls the chaotic early days as "bolting the wings on the plane as it took off." Third was culture. To avoid the backstabbing that plagued other campaigns, they enforced a strict "no assholes" rule, fostering a loyal, disciplined environment that became known as "No Drama Obama." Fourth was strategy. The campaign manager, David Plouffe, was a political chess player, always thinking several moves ahead and refusing to get distracted by the daily news cycle.

Finally, and most crucially, was branding. The message of "Change We Can Believe In" wasn't just a slogan created in a focus group; it was an authentic extension of Obama’s own story and vision. This stood in stark contrast to Hillary Clinton’s more poll-tested messaging. By blending grassroots organizing with new technology and an authentic narrative, the campaign created a movement that rewrote the rules of modern politics.

The Death of the Bully Pulpit

Key Insight 2

Narrator: Upon entering the White House, Pfeiffer and the Obama team quickly discovered that governing was not campaigning. The president’s ability to command national attention and drive a message—the so-called "bully pulpit"—was dying. The media landscape had fractured into a million pieces. The rise of social media, the decline of local newspapers, and the 24/7 cable news cycle created what Pfeiffer calls the "SportsCenter Effect" in politics, where style was elevated over substance, and gaffes were treated with more importance than policy.

In this new environment, authenticity was paramount. Pfeiffer illustrates this with two contrasting stories. In 2009, the team arranged for Obama to be the first sitting president to appear on a late-night talk show, The Tonight Show with Jay Leno. While establishment figures in Washington balked, calling it unpresidential, the appearance was a massive success. It was authentic to Obama’s personality and allowed him to connect with a huge audience on his own terms.

A few months later, however, the communications team tried to replicate this success by arranging an interview for Obama with ESPN’s NASCAR Now. The idea was to reach a different demographic, but the execution was a disaster. Obama knew little about NASCAR, and the interview was painfully awkward. The lesson was clear: in a fragmented media world, the cleverest strategy will fail if it isn't genuine to the person delivering the message.

The Rise of the Right-Wing Propaganda Machine

Key Insight 3

Narrator: While the Obama administration was learning to navigate the new media landscape, a powerful force was working to create an entirely separate reality. Pfeiffer argues that Fox News is not a news organization but a "propaganda outlet with a specific political agenda." He details how the network systematically worked to undermine the Obama presidency from day one.

One of the most damaging examples was the "death panel" conspiracy. In 2009, as the administration debated the Affordable Care Act, former governor Sarah Palin posted on Facebook that the bill would create "death panels" to decide who was worthy of care. This was a complete fabrication. The provision in question was about funding for voluntary end-of-life counseling. Yet, Fox News and Republican leaders seized on the lie, repeating it endlessly until it became a central point of opposition to the healthcare bill. Despite being debunked repeatedly, polls years later showed that nearly a third of Americans, almost all Republicans, still believed it was true. This incident revealed a terrifying new reality: a lie, if repeated loudly and often enough by a trusted source, could become more powerful than the truth.

How Republican Radicalization Paved the Way for Trump

Key Insight 4

Narrator: The rise of misinformation was a symptom of a deeper disease: the radicalization of the Republican Party. Pfeiffer argues that the election of the first Black president broke something within the GOP. Their response was not policy-based opposition but a strategy of total, unconditional obstruction, driven by a base that was fed a steady diet of fear and resentment by right-wing media.

A telling anecdote reveals the depth of this intransigence. After Republicans won the House in 2010, the White House proposed a bipartisan dinner to find common ground. The Republicans refused. Their leadership privately admitted to Obama’s staff that they couldn't risk being photographed "breaking bread" with the president, for fear of angering their voters. This wasn't about policy differences; it was about a refusal to even acknowledge the legitimacy of the opposition.

This dynamic, where the Republican establishment was held hostage by its most extreme elements, created the perfect environment for a figure like Donald Trump. He didn't create the party's anger and paranoia; he simply recognized it, validated it, and rode it all the way to the White House. The GOP had spent eight years telling its voters that Obama was an illegitimate, foreign-born enemy of the state. It was only a matter of time before someone came along who actually believed it.

A New Playbook for a New Era

Key Insight 5

Narrator: The 2016 election was the tragic culmination of these trends. Pfeiffer argues that the Clinton campaign failed because it ran a traditional campaign in a completely new and unconventional political environment. It was focused on policy and qualifications, while Trump was running a reality show, dominating the media landscape with outrage and spectacle.

The path forward, Pfeiffer contends, is not to go back to the old rules of civility and bipartisanship. That world is gone. The Republican Party has become an entity that is hostile to facts, compromise, and democratic norms. Therefore, Democrats must stop trying to meet them in the middle. Instead, they must build their own media ecosystem to counter the right-wing propaganda machine and speak directly to voters. They must fight to win elections decisively, not by adopting the other side's tactics of lies and division, but by offering a compelling, hopeful, and truthful vision for the future. The goal is not just to defeat a single politician, but to defeat the cynical and destructive brand of politics that he represents.

Conclusion

Narrator: The single most important takeaway from Yes We (Still) Can is that the political and media landscape has been fundamentally rewired. The old assumptions about shared facts, good-faith debate, and the power of the presidency to shape a national conversation no longer apply. We now live in an era of fractured realities, where propaganda can be more potent than truth and where the primary goal of one of our two major parties is often obstruction, not governance.

Pfeiffer’s account is a sobering warning, but it is not a message of despair. It is a call to action. The book challenges us to stop longing for a political past that no longer exists and to start building the tools and strategies needed to win the future. The most challenging question it leaves us with is this: In an age of rampant misinformation and political tribalism, how do we fight for what is true without becoming as cynical and divisive as the forces we are fighting against?

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