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Tired of Winning

Donald Trump and the End of the Grand Old Party

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22 minutes read | Text | 8 key ideas
In a turbulent swirl of power plays and political drama, "Tired of Winning" pulls back the curtain on Donald Trump's dramatic reinvention of the Republican Party. From the sun-soaked exile of Mar-a-Lago, Trump emerges more emboldened and unyielding than ever, casting a long shadow over the GOP's future. Jonathan Karl, with decades of firsthand experience, chronicles Trump's audacious comeback and the GOP's precarious crossroads—an existential choice that echoes Reagan's call to action from sixty years ago. Here lies a tale of ambition, vendetta, and the relentless pursuit of influence—a provocative exploration of the man who refuses to fade quietly into history.

Categories

Nonfiction, Biography, History, Politics, Audiobook, Journalism, Historical, Presidents, American History, Government

Content Type

Book

Binding

Kindle Edition

Year

2023

Publisher

Dutton

Language

English

ASIN

B0C48NJY3D

ISBN

059347399X

ISBN13

9780593473993

File Download

PDF | EPUB

Tired of Winning Plot Summary

Introduction

January 6, 2021 marked a pivotal moment in American political history. As rioters stormed the U.S. Capitol, the peaceful transfer of power—a hallmark of American democracy for over two centuries—was violently disrupted. This shocking event would become the starting point of Donald Trump's post-presidential journey, a period characterized by remarkable highs and devastating lows. The transition from the most powerful office in the world to private citizenship is challenging for any former president, but Trump's post-White House years have been uniquely tumultuous. What happens when a former president refuses to accept electoral defeat? How does a political movement evolve when its charismatic leader faces mounting legal troubles? These questions lie at the heart of this exploration of Trump's post-presidency. Through meticulous reporting and insider accounts, readers gain unprecedented insight into the former president's attempts to maintain relevance, the fracturing of his political coalition, and his legal battles that culminated in multiple indictments. This narrative offers valuable perspective for anyone seeking to understand contemporary American politics, the fragility of democratic institutions, and the complex interplay between personality and power in the modern political landscape.

Chapter 1: The Shattered Presidency: January 6th and Its Aftermath

January 6, 2021, marked the nadir of Donald Trump's presidency - a day when his desperate attempts to cling to power culminated in violence at the U.S. Capitol. As his supporters stormed the building, Trump's response was not to immediately condemn the violence, but to watch it unfold on television from the White House dining room for nearly three hours. This period of inaction, from 1:21 p.m. until 4:03 p.m., is documented in White House logs that show a complete blank - not because records were erased, but because the president did nothing official during this critical time. Trump's failure of leadership that day was comprehensive. While Vice President Mike Pence was making urgent calls to the Pentagon requesting National Guard assistance, Trump was calling senators trying to delay the certification of electoral votes. When Republican House Leader Kevin McCarthy called Trump during the riot and urged him to call off his supporters, Trump reportedly shrugged it off, telling McCarthy the rioters just cared more about the stolen election than McCarthy did. Even Trump's closest advisors were horrified. White House Counsel Pat Cipollone testified that there "needed to be an immediate and forceful response, statement, public statement, that people need to leave the Capitol now." The aftermath of January 6th revealed just how isolated Trump had become. When he left the White House for the last time on January 20, 2021, few officials from his administration bothered to attend his farewell ceremony. Vice President Pence was notably absent, choosing instead to attend Joe Biden's inauguration. On Air Force One during that final flight, Trump told Republican National Committee chairwoman Ronna McDaniel, "I'm done. I'm starting my own party." When McDaniel protested that this would destroy the GOP, Trump responded coldly: "Exactly. You lose forever without me. This is what Republicans deserve for not sticking up for me." Upon arriving at Mar-a-Lago, Trump entered a period of darkness and isolation. Club members would applaud when he appeared for dinner, but on at least one occasion, he got up from the table in the middle of his meal and left without explanation. The man who had played hundreds of rounds of golf as president suddenly found it difficult to make it through eighteen holes, picking up his ball in the middle of one round and going home. Trump's fall from grace was so complete that some of his cabinet members considered invoking the 25th Amendment to remove him from office in his final days. Education Secretary Betsy DeVos explored this option before resigning, and Treasury Secretary Steven Mnuchin and Secretary of State Mike Pompeo discussed the possibility as well. As Mnuchin later admitted under oath, "I do recall speaking to Secretary Pompeo about the 25th Amendment. It came up very briefly in our conversation." The political wilderness for Trump lasted just eight days. On January 28, 2021, Kevin McCarthy visited Mar-a-Lago, effectively restoring Trump's status as the party's leader. The message of McCarthy's pilgrimage was clear: the Republican Party would continue to be defined by Donald Trump, despite the catastrophe he had just inflicted upon the nation.

Chapter 2: Delusions of Reinstatement: The Big Lie Takes Hold

In the aftermath of his 2020 election defeat, Donald Trump embarked on an extraordinary journey into fantasy. By March 2021, just weeks after leaving the White House, he had begun entertaining the notion that he might somehow be reinstated as president before the 2024 election. This belief, while completely detached from constitutional reality, became a central fixation for the former president throughout 2021. The reinstatement fantasy took various forms, but gained significant momentum when Mike Lindell, the MyPillow CEO and fervent Trump supporter, began publicly declaring that Trump would return to office by August 2021. "Donald Trump will be back in office in August," Lindell proclaimed on Steve Bannon's War Room podcast. "The election of 2020 is going bye-bye." Trump latched onto this timeline, telling confidants he expected to be back in the White House by summer's end. When Republican congressman Mo Brooks received a call from Trump in March 2022, the former president demanded Brooks issue a statement calling for Biden to be removed from office and Trump reinstated immediately. What made this delusion particularly dangerous was Trump's willingness to pressure officials to act on it. In his conversation with Brooks, Trump insisted the congressman call for "rescission of the election," the "immediate removal of Joe Biden," and Trump's reinstatement as president. Brooks refused, telling Trump, "It's not the truth." Trump's response was telling - he erupted in anger, using profanities before hanging up. As Brooks later recounted, "It's pretty clear he's used to people doing what he says, even if it violates the law." The reinstatement fantasy wasn't merely a private obsession. Trump signaled his belief publicly, ending one statement with the cryptic phrase "2024 or before!" When directly asked about this possibility in a July 2021 interview, Trump responded, "I'm not going to explain it to you, Jonathan, because you wouldn't either understand it or write it." This wasn't just political posturing - those close to Trump confirmed he genuinely believed reinstatement was possible. By summer 2021, Trump's fixation had become so consuming that even his own aides grew concerned. One junior aide at Mar-a-Lago told him, "If you really think it's true, then stop talking about it. Just let it happen. If you keep talking about it so much, people will think you are crazy." Trump's response was revealing: "You say that because you aren't a true believer!" The aide replied, "No, I just believe in the Constitution." The reinstatement fantasy represented more than just a refusal to accept defeat - it revealed a fundamental break with reality that would define Trump's post-presidency period and set the stage for his increasingly desperate attempts to regain power by any means necessary.

Chapter 3: The Arizona Obsession: Failed Audits and Conspiracy Theories

In the spring of 2021, Donald Trump became fixated on an extraordinary effort unfolding in Arizona - a massive audit of every ballot cast in Maricopa County during the 2020 election. For Trump, this wasn't just about setting the record straight; he genuinely believed it would be the first domino to fall in a process that would ultimately return him to the White House before the 2024 election. The Arizona audit was unprecedented in its scope and peculiarity. Rather than selecting one of several reputable election technology companies that had submitted bids, Arizona Senate Republicans chose Cyber Ninjas, a small Florida-based cybersecurity firm with no experience conducting election audits. The company's CEO, Doug Logan, had previously promoted some of the most far-fetched conspiracy theories about the 2020 election, including claims involving the late Venezuelan dictator Hugo Chávez and alleged ties between China and Dominion Voting Systems. What began as a project expected to take just a few weeks dragged on for more than four months, ballooning in cost from the $150,000 originally allocated to millions of dollars. The audit was partially funded by some of the most extreme figures in Trump's orbit - including $600,000 from an organization led by One America News hosts, nearly $1 million from a group affiliated with Michael Flynn, and more than $500,000 from Sidney Powell's Defending the Republic. As Maricopa County Board of Supervisors chairman Jack Sellers, a Republican, described it: "a grift disguised as an audit." Trump was obsessed with the process, constantly checking in on the livestream being broadcast by One America News. "One America News (OAN), one of the fastest growing networks on television, and the 'hottest,' is doing a magnificent job of exposing the massive fraud that took place," Trump declared in a statement. He even referenced the audit during appearances at Mar-a-Lago, telling guests, "It's on closed-circuit, I guess it's on all over the place because everyone's talking about it." The methods employed by Cyber Ninjas veered into the absurd. Volunteers were observed scanning ballots with ultraviolet light, searching for secret watermarks that didn't exist. Others took pictures of ballots with special cameras, looking for traces of bamboo that would supposedly prove ballots had been flown in from Asia. Ken Bennett, Arizona's Trump-supporting former secretary of state who served as a liaison for the audit, later revealed that Cyber Ninjas CEO Doug Logan held daily meetings with state senator Wendy Rogers to provide updates to the audit's funders - and possibly Trump himself. When Cyber Ninjas finally released their findings in September 2021, the results were devastating to Trump's narrative. After months of work, they found 99 more votes for Biden and 261 fewer for Trump than the original count. The audit had confirmed Biden's victory in Arizona by a slightly larger margin than before. "Truth is truth and numbers are numbers," Republican state senate leader Karen Fann conceded as the auditors presented their report. Trump frantically tried to spin the results, issuing six increasingly desperate statements on the day the report was released. "The Fake News is lying about the Arizona audit report!" he claimed, later adding, "It is not even believable the dishonesty of the Fake News Media on the Arizona audit results, which shows incomprehensible Fraud at an Election Changing level." Within hours, a fabricated "real" report claiming the election "should not be certified" was circulating online, but even the audit's biggest proponents acknowledged it was fake. The Arizona audit's failure marked a significant blow to Trump's reinstatement fantasy. As David Becker of the Center for Election Innovation and Research observed, "If Trump and his supporters can't prove it here, with a process they designed, they can't prove it anywhere." Nevertheless, Trump continued to insist the 2020 election was stolen, setting the stage for his increasingly desperate attempts to maintain relevance and reclaim power.

Chapter 4: Legal Walls Closing In: From Plaintiff to Defendant

The trajectory of Trump's post-presidency took a dramatic turn as his role in the legal system transformed from plaintiff to defendant. Initially, Trump and his allies filed dozens of lawsuits challenging the 2020 election results, virtually all of which were dismissed for lack of evidence or standing. These legal defeats, however, were merely the prelude to a far more serious legal reckoning that would come to define his post-White House years. By 2022, Trump faced mounting legal challenges on multiple fronts. The Justice Department was investigating his handling of classified documents found at Mar-a-Lago, while a special grand jury in Georgia examined his efforts to overturn that state's election results. In New York, both the state attorney general and the Manhattan district attorney were conducting investigations into his business practices. These weren't just political nuisances—they represented existential threats to Trump's freedom, reputation, and financial empire. The Mar-a-Lago documents case proved particularly damaging. In August 2022, FBI agents executed a search warrant at Trump's Florida residence, recovering dozens of classified documents that he had failed to return despite multiple opportunities to do so. The unprecedented search of a former president's home shocked the nation and forced Republicans to choose between defending Trump and respecting the rule of law. Trump responded with characteristic defiance, claiming he had declassified the documents "by thinking about it" and suggesting the FBI had planted evidence—claims that further eroded his credibility with all but his most devoted supporters. Trump's legal strategy revealed much about his post-presidential mindset. Rather than cooperating with investigators or mounting conventional defenses, he relied on delay tactics, public attacks on prosecutors and judges, and attempts to politicize the legal process. He hired and fired attorneys at a dizzying pace, often preferring lawyers who would echo his grievances on television rather than those with relevant expertise. This approach reflected Trump's continued belief that the rules didn't apply to him and that political pressure could overcome legal jeopardy. The culmination of these legal battles came in 2023, when Trump became the first former president in American history to face criminal charges. In March, a Manhattan grand jury indicted him on 34 felony counts related to falsifying business records. By summer, federal indictments followed for the classified documents case and for his efforts to overturn the 2020 election, including his actions leading up to January 6th. A fourth indictment in Georgia charged Trump and 18 co-defendants with racketeering for their attempts to subvert that state's election results. These indictments transformed Trump's political narrative. What had begun as a story about a former president seeking vindication became a tale of a potential felon fighting to stay out of prison. For Trump's base, the indictments reinforced their belief that he was being persecuted by a "deep state" determined to prevent his return to power. For others, including many Republicans who had previously supported him, the mounting legal troubles raised serious questions about Trump's fitness to serve again. The legal battles not only consumed Trump's time and resources but fundamentally altered the calculus of his potential 2024 presidential campaign.

Chapter 5: The Midterm Disaster: Electoral Rejection in 2022

The 2022 midterm elections represented a critical test of Trump's continued influence over the Republican Party and American politics more broadly. In the lead-up to November, Trump had positioned himself as the party's kingmaker, endorsing candidates in primaries across the country and demanding loyalty to his election fraud claims as a litmus test for his support. This strategy produced a slate of Republican nominees who were deeply aligned with Trump but often lacked traditional qualifications or appeal to moderate voters. As Election Day approached, Republicans were widely expected to achieve a "red wave," potentially winning back both chambers of Congress by substantial margins. Historical patterns favored the GOP, as the president's party typically loses seats in midterm elections. Additionally, President Biden's approval ratings were underwater, and voters consistently ranked inflation and the economy—traditionally Republican strengths—as their top concerns. Trump confidently predicted that Republicans would win big and that he deserved "all of the credit" for their anticipated success. The actual results delivered a stunning rebuke to Trump and his endorsed candidates. Democrats maintained control of the Senate and limited Republican gains in the House to a razor-thin majority, defying historical precedent and polling predictions. In the most competitive races, Trump-endorsed candidates consistently underperformed, with notable losses in Pennsylvania, Arizona, Georgia, and other battleground states. Post-election analyses found that Trump-backed candidates performed approximately 5 percentage points worse than traditional Republicans, suggesting that Trump's influence had become a significant electoral liability. The pattern was unmistakable: candidates who embraced Trump's election denial and MAGA rhetoric fared poorly with moderate and independent voters. In Georgia, for instance, Republican Governor Brian Kemp, who had resisted Trump's pressure to overturn the 2020 results, won reelection by a comfortable margin, while Trump-endorsed Senate candidate Herschel Walker lost to Democratic incumbent Raphael Warnock. Similar dynamics played out across the country, with Republicans who maintained some independence from Trump generally outperforming those who tied themselves closely to him. Trump's reaction to the disappointing results revealed his inability to accept responsibility for failure. At an election night gathering at Mar-a-Lago, he appeared visibly agitated as results came in, eventually delivering a brief, subdued speech before leaving the event early. In subsequent days, he blamed others for the losses, including Senate Republican leader Mitch McConnell and his wife Elaine Chao, while insisting that his endorsed candidates had actually performed well despite evidence to the contrary. The midterm disaster prompted unprecedented criticism of Trump from within Republican ranks. Former allies like Chris Christie declared Trump a "three-time loser" who had cost the party winnable elections in 2018, 2020, and now 2022. Conservative media outlets like the New York Post and Fox News began giving Trump less coverage and treating him with greater skepticism. Even longtime supporters acknowledged privately that Trump's fixation on 2020 and his personal grievances had become political liabilities. For the first time since he descended the golden escalator in 2015, Trump's grip on the Republican Party appeared to be genuinely weakening.

Chapter 6: A Diminished Return: The Troubled Third Campaign Launch

On November 15, 2022, just one week after the midterm election debacle, Donald Trump stood before a crowd at Mar-a-Lago and announced his third campaign for the presidency. The timing was deliberate—Trump had hoped to capitalize on what he expected would be a Republican wave in the midterms, positioning himself as the natural leader of a resurgent party. Instead, he launched his campaign under a cloud of blame for the party's underperformance, creating an inauspicious start to his 2024 bid. The announcement itself reflected Trump's diminished stature. The crowd at Mar-a-Lago was notably smaller than at previous Trump events, with many prominent Republicans and even some family members conspicuously absent. Trump delivered a subdued, teleprompter-driven speech that lacked his usual energy and improvisational flair. Media coverage was limited, with several networks cutting away before he finished speaking. Even Fox News, long a reliable Trump ally, gave the announcement only partial coverage, signaling a shift in the conservative media landscape. In the weeks following his announcement, Trump's campaign showed signs of serious dysfunction. He remained largely confined to Mar-a-Lago, venturing out only to play golf at his nearby properties. Campaign events were virtually non-existent, and hiring for key positions proceeded slowly. Perhaps most damaging was Trump's series of self-inflicted controversies, including a dinner with white nationalist Nick Fuentes and antisemitic rapper Kanye West, a call to terminate the Constitution to reinstate himself as president, and the bizarre launch of digital trading cards featuring himself as a superhero. Trump's legal troubles continued to overshadow his campaign messaging. Rather than focusing on policy proposals or critiques of the Biden administration, Trump devoted much of his public communication to attacking prosecutors, judges, and witnesses involved in his various cases. This defensive posture prevented him from articulating a forward-looking vision that might appeal to voters beyond his base. When he did address policy issues, his proposals often seemed half-formed or contradictory, suggesting a candidate more focused on grievance than governance. By spring 2023, polling showed Trump maintaining a lead in the Republican primary field but facing significant vulnerabilities. His favorability ratings among the general electorate remained deeply underwater, and a growing number of Republicans expressed openness to alternatives. Several prominent Republicans, including Florida Governor Ron DeSantis, former Vice President Mike Pence, and former Trump administration officials Nikki Haley and Mike Pompeo, began positioning themselves for potential primary challenges, sensing Trump's weakness. Perhaps most concerning for Trump's prospects was the apparent erosion of his mystique. The aura of invincibility that had surrounded him since his unexpected 2016 victory had been punctured by repeated electoral defeats and legal setbacks. Republican donors and elected officials who had once feared crossing him began speaking more openly about the need for the party to move on. Even some of his most loyal supporters privately acknowledged that his path to another term in the White House had narrowed considerably. The man who had dominated American politics for seven years found himself in an unfamiliar position: fighting not just for another chance at power, but for continued relevance in a political landscape that was beginning to evolve beyond him.

Summary

The trajectory of Donald Trump's post-presidency reveals a fundamental tension in American politics: the conflict between personality-driven populism and institutional resilience. Trump's refusal to accept electoral defeat and his subsequent efforts to maintain power—through election fraud claims, pressure on officials, and ultimately the January 6th insurrection—tested the strength of democratic guardrails. While these institutions ultimately held, the damage inflicted on public trust in elections and peaceful transfers of power may take generations to repair. Throughout this period, Trump's personal grievances increasingly overshadowed any coherent political vision, transforming him from the leader of a movement to the center of a cult of personality detached from traditional policy goals. The lessons of this tumultuous period extend beyond one man's political journey. First, democracies are more fragile than they appear, requiring constant vigilance and institutional reinforcement to withstand authoritarian pressures. Second, political movements built primarily around individual personalities rather than enduring principles tend to become increasingly extreme and detached from reality over time. Finally, the power of narrative in politics often trumps factual reality—millions of Americans continue to believe demonstrably false claims about the 2020 election because these narratives align with their identity and worldview. Moving forward, rebuilding democratic norms will require not just institutional reforms but a renewed commitment to shared truth and civic responsibility across the political spectrum. The ultimate legacy of this period may depend on whether Americans choose to learn from this near-miss of democratic collapse or continue down a path of partisan tribalism that makes such crises increasingly likely.

Best Quote

“He lacks any shred of human decency, humility or caring,” the former White House official wrote of the man he had served for more than a year. “He is morally bankrupt, breathtakingly dishonest, lethally incompetent, and stunningly ignorant of virtually anything related to governing, history, geography, human events or world affairs. He is a traitor and a malignancy in our nation and represents a clear and present danger to our democracy and the rule of law.” ― Jonathan Karl, Tired of Winning: Donald Trump and the End of the Grand Old Party

Review Summary

Strengths: The review praises Jonathan Karl's reporting skills, noting that he is "always at the top of his reporting game." It highlights the book's ability to provide new information and insights, describing it as a "scorching takedown" of Trump and his associates. The book is also recognized for its contribution to the historical record of Trump's presidency and its aftermath. Weaknesses: The review points out some repetition between this book and Karl's previous works, suggesting a lack of fresh content in certain areas. Overall Sentiment: Enthusiastic Key Takeaway: The book offers a compelling and critical examination of Trump's presidency and its ongoing impact, emphasizing the importance of safeguarding American democracy against internal threats. Despite some repetition, it provides valuable new insights and serves as a significant historical account.

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Jonathan Karl

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Tired of Winning

By Jonathan Karl

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