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Siege

9 min

Trump Under Fire

Introduction

Narrator: What if a president viewed the law not as a boundary, but as an obstacle to be bulldozed? What if he saw his own lawyers not as counselors, but as "fixers," whose only job was to make problems disappear, no matter the cost? This is the chaotic world at the heart of Michael Wolff's book, Siege: Trump Under Fire. It chronicles the second year of the Trump presidency, a period defined by escalating legal threats, internal paranoia, and a commander-in-chief who, when faced with a subpoena for his business records, didn't ask about legal strategy. Instead, he raged, "Where's my Roy Cohn?"—invoking the infamous, ruthless attorney who had served as his mentor. Wolff's account argues that to understand this presidency, one must first understand the man at its center, a figure who believed he was under siege from the very institutions he was elected to lead.

The President's War on His Own Lawyers

Key Insight 1

Narrator: In Trump's worldview, the legal system was just another opponent to be dominated. He didn't want legal advice; he wanted problems to vanish. This core belief created a constant, simmering conflict with his own legal team. His lawyers, from Don McGahn to John Dowd, were judged not on their legal acumen but on their ability to produce solutions and, most importantly, to reassure him. A favorite refrain in the West Wing was Trump’s demand for a letter from the special counsel, Robert Mueller, personally exonerating him. When this letter never materialized, he berated his staff, shouting, "Where is my fucking letter?"

This desire for a "fixer" over a lawyer was rooted in his admiration for two figures: Roy Cohn, the notoriously aggressive attorney, and Bobby Kennedy, who he saw as his brother's loyal hatchet man. Trump frequently lamented, "Where's my Roy Cohn and Bobby Kennedy?" This wasn't a search for legal expertise; it was a search for absolute, weaponized loyalty. This perspective created a toxic environment where lawyers were expected to bend the truth. When Hope Hicks, one of his closest aides, admitted to telling "white lies" for the president, it was seen not as a failure of integrity, but as a baseline expectation in a White House where the truth was perpetually negotiable.

The Ghost in the Machine: Steve Bannon's Enduring Influence

Key Insight 2

Narrator: Though ousted from the White House, Steve Bannon remained one of the most influential and disruptive forces in Trump's orbit. Operating from his Washington townhouse, dubbed "the Embassy," Bannon saw himself as the true guardian of the populist revolution. He believed Trump himself was merely a flawed vessel for a much larger movement. Bannon’s influence was most potent during the battle over the 2018 congressional budget. When Trump was initially convinced by Republican leadership that the $1.3 trillion bill funded his border wall, Bannon, along with Fox News hosts, quickly disabused him of the notion.

They framed the bill, which allocated only a fraction of the requested funds, as a total betrayal by the establishment. Bannon mobilized the base, and Trump, incensed and feeling duped, threatened a veto. Though he ultimately signed the bill, the episode demonstrated Bannon's power to shape the narrative and steer the president. Bannon’s long-term strategy was to save Trump from himself and the "elites," even devising a radical plan to fire Deputy Attorney General Rod Rosenstein and retroactively claim executive privilege over White House communications to cripple the Mueller investigation. He saw the presidency not as a job, but as a war, and he was determined to be its chief strategist, whether from inside the West Wing or out.

The Unraveling of the West Wing

Key Insight 3

Narrator: By the spring of 2018, the Trump White House was in a state of advanced decay. The initial chaos had given way to a deep, systemic dysfunction. This was perfectly captured in the disastrous nomination of the White House doctor, Ronny Jackson, to head the Department of Veterans Affairs. Trump had a personal "crush" on Jackson, who had famously lavished praise on the president's health. The nomination, however, was based on little more than this flattery.

What followed was a masterclass in internal sabotage. The office of Vice President Mike Pence, led by his ambitious chief of staff Nick Ayers and his wife Karen, allegedly orchestrated a campaign to sink the nomination. Karen Pence reportedly held a grudge against Jackson for an indiscretion regarding a personal medical issue. Soon, a flood of anonymous allegations about Jackson's on-the-job drinking and loose handling of prescriptions appeared in the press, forcing him to withdraw. The incident was a stunning display of the administration's internal rot. It showed that the president's power was limited, his wishes could be subverted by personal vendettas, and the so-called "adults in the room" were engaged in their own ruthless power games.

The Helsinki Summit: A Portrait of Deference

Key Insight 4

Narrator: The July 2018 summit with Vladimir Putin in Helsinki stands as one of the most controversial moments of the Trump presidency. Against the advice of his national security team, Trump met with the Russian president alone for two hours, with only translators present. The public press conference that followed was a public relations catastrophe. Standing next to Putin, Trump stunned the world by appearing to accept the Russian leader's denial of election interference over the unanimous conclusion of his own intelligence agencies.

The fallout was immediate and bipartisan. Back in Washington, the White House was in full-blown panic mode. Officials scrambled to do damage control, but Trump himself was a major obstacle. He refused to brief his team on what was said in the private meeting, leaving his own administration in the dark. The performance was so alarming that it sparked serious discussions among Republicans about a potential primary challenge in 2020. For critics, the Helsinki summit was the ultimate proof of Trump's strange deference to Putin, a moment where he seemed to act not as the President of the United States, but as a subordinate to a foreign adversary.

The Shutdown and the Wall: A Crisis of Trump's Own Making

Key Insight 5

Narrator: In the final weeks of 2018, the presidency spiraled into a new crisis, this time entirely of its own making. Goaded by criticism from conservative commentators like Ann Coulter, who called him a "gutless president" for failing to secure funding for his border wall, Trump plunged the government into a shutdown. He refused to sign any spending bill that didn't include the $5.7 billion he demanded for the wall, a promise that had become the central, non-negotiable symbol of his presidency.

The shutdown dragged on for 35 days, the longest in U.S. history. Inside the White House, Trump grew increasingly isolated and erratic. He was reportedly obsessed with his Secret Service detail, feeling like a "prisoner." The standoff revealed his susceptibility to pressure from his base and the media figures who stoked its passions. Ultimately, Trump capitulated, reopening the government without securing the funds. He then declared a national emergency to build the wall, a move that was immediately challenged in court. The entire episode, from the impulsive shutdown to the legally dubious emergency declaration, encapsulated the siege mentality of the administration: a president cornered by his own promises, lashing out in a desperate attempt to claim victory, even as the walls closed in.

Conclusion

Narrator: Ultimately, Siege portrays a presidency defined by a singular, all-consuming reality: the character of Donald Trump himself. The book argues that despite the Mueller report not finding a criminal conspiracy, Trump's true vulnerability was never just about a single investigation. It was about his fundamental nature—his transactional relationships, his disregard for norms, and his deep-seated belief that loyalty was a one-way street. He survived the siege described by Wolff, but the book leaves readers with a chilling question. When a leader's character is the central, chaotic force in a government, can the institutions of democracy truly hold, or are they destined to be warped and weakened by the constant, unrelenting pressure?

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