Triumph of the Wily: Donald Trump, Comeback King
- Mark Chin
- Nov 11, 2024
- 14 min read

Love him or hate him, Donald Trump sure knows how to make a comeback.
His first term in office ended in chaos and condemnation - even from members of his own party. Given his victory on Tuesday, November 5th (only the second time anyone has ever returned to the White House after previously losing a presidential re-election bid), Trump has not only been given that rarest of political gifts – a second chance, he has an opportunity for redemption and greatness, if only he could overcome those aspects of his nature that marred his previous tenure.
Nonetheless, he has achieved an astonishing comeback for the ages. And he has done so with pugilistic finesse.
Americans love a fighter. Even those who think he is anathema to everything they believe in must admit to some degree of admiration for a man whose relentless will to win – at any cost – compelled him to struggle so mightily for a role he does not seem to actually like.
It’s nothing less than an extraordinary reversal of fortune for the 78-year-old former president which has vaulted him back into the White House as a man who seems politically bulletproof, with sweeping plans to remake America (and by extension, the world) with ranks of loyalists behind him and complete control of the levers of power.
It would have been so simple to write him off. Four years ago, Trump indeed appeared a beaten man. His Democratic opponent, Joe Biden, had defeated him by both a comfortable electoral and popular vote margin in the 2020 presidential contest. Trump seemed to have been relegated by vox populi to the same ignominy as Jimmy Carter and George H.W. Bush, single term presidents both. With the possible exception of James K. Polk (who actually pledged to only serve four years), most American commanders-in-chief are generally regarded as “successful” having had eight years in office.
Courts had batted away his attempts to contest those results. His last-ditch rally in which he urged his supporters to march on the US Capitol as lawmakers were certifying Biden’s victory culminated in the crowd launching a violent attack that sent those inside scrambling for safety. Hundreds of law enforcement officers were injured, and the image of American political stability had been severely tarnished. If it could happen there, it could happen anywhere.
Education Secretary Betsy DeVos and Transportation Secretary Elaine Chao were among a spate of Trump administration officials who quit in protest. “There is no mistaking the impact your rhetoric had on the situation, and it is the inflection point for me,” DeVos wrote in her letter of resignation to the president. Hardly a ringing endorsement from someone who’d been seen as a close supporter, much less a cabinet member.
Even South Carolina Republican Senator Lindsey Graham, one of Trump’s closest allies, broke with the president. “All I can say is count me out,” he said on the floor of the Senate. “Enough is enough.”
The movement away from Trump extended into the corporate world, as dozens of large companies – including American Express, Microsoft, Nike and Walgreens – announced they were suspending support for Republicans who had challenged the results of the 2020 election. His coattails, it appeared, were actually banana skins, tripping up his supporters.
And he didn’t help matters by appearing petulant at best, a bad loser at worst. On the day of Biden’s inauguration, Trump broke with 152 years of tradition by declining to attend the ceremony, instead flying back to his private club in Mar-a-Lago earlier that morning, accompanied by a handful of his closest aides and family, leaving then Vice President Mike Pence to represent the outgoing administration in his stead.
That day, it was obvious that his mood was sullen, and it was easy to see why. Not only had he lost to a man whom he’d denigrated as slow, dull-witted and a loser, Trump was likely angry, frustrated, unsure of how to spend his days and without a plan for his political future. Not for him the lecture circuit, penning of memoirs or raising funds for a presidential library.
The media coverage and political chatter that month reflected this uncertainty over his future. After a clear electoral defeat followed by the chaotic scenes at the Capitol, some were even more definitive, suggesting there could be no way back:
“And just like that, the bold, combustible and sometimes brilliant political career of Donald J. Trump comes to an end,” one opinion piece read. The subheading of an opinion piece in in a venerable daily declared: “The terrible experiment is over.” The headline was even more direct: “President Donald J. Trump: The End.”
Trump appeared to be heading for the political equivalent of Napoleon’s Elba: permanent exile from power. Yet even then he hinted at what was to come: his determination to make it St. Helena instead: a triumphant return from the wilderness He would not go quietly into the good night.
“We love you,” he said in remarks to supporters on a Maryland Air Force base tarmac. “We will be back in some form.”
And this statement in a nutshell, sums up Donald Trump. He simply does not like to lose. Call it vainglory, delusion, or a messiah complex but ever since a childhood where his father encouraged and cajoled him to compete for everything and corporate lawyer Roy Cohn mentored him to be relentless, Trump has never accepted defeat as a permanent state.
A week later, it became clear that Trump wouldn’t have to wait long to assert his continued political influence. The party came back to him. California Congressman Kevin McCarthy, the Republican leader in the House of Representatives, paid the former president a visit at Mar-a-Lago, posing for a photo next to a beaming Trump.
It was nothing less than an astonishing volte face. In the immediate aftermath of the 6 January attack, McCarthy had said that Trump “bears responsibility” for the mob violence and recommended that Congress formally censure him for his conduct. Now he was pledging to work with the former president to win a congressional majority in the next year’s mid-term elections.
Even as the Democrat-controlled US Senate was preparing to hold Trump’s impeachment trial, McCarthy’s Palm Beach pilgrimage illustrated that one of the most powerful Republicans in Congress still viewed the former president as a kingmaker. McCarthy’s visit really opened the door for Trump, acting as a permission slip to Republicans who had criticized Trump to forgive him and move on.
Trump’s Senate trial would end in acquittal, as most Republicans – including some outspoken critics like minority leader Mitch McConnell – voted against a conviction that could have led to the former president being banned from future elective office. McConnell had said that Trump’s conduct on 6 January was “a disgraceful dereliction of duty”, but he chose not to take the one step that could have conclusively ended the former president’s political career – perhaps out of fear of effectively ending his own, for the MAGA movement was still very much alive.
Republicans also worried that the former president might start a third party that would siphon off support from Republicans – concerns that Trump’s closest aides did little to dispel.
The former president spent the next month mostly within the comfortable confines of his Mar-a-Lago club, venturing out only for a round of golf or a private dinner. By the end of February, as the furor around 6 January ebbed, he was ready to hold his first public event. At the Conservative Political Action Conference – the right-wing confab typically held near Washington, DC but relocated to Orlando, Florida, due to Covid restrictions – the former president demonstrated that he still commanded the loyalty of the Republican base. Addressing thousands of cheering supporters in a sprawling hotel conference centre, Trump basked in the glow of their adoration.
“I stand before you today to declare that the incredible journey we began together,” he said, “is far from over.” He also hinted, coyly, that he might beat the Democrats “for a third time” in 2024.
An official straw poll of conference attendees only underlined what by then was obvious. Sixty-eight percent of respondents said Trump should run again. Fifty-five percent said they would vote for him in a contested primary – more than double the second-place candidate, Florida Governor Ron DeSantis.
After a brief hiatus, Trump reactivated his steady stream of fundraising emails to supporters and resumed holding his carnival-like outdoor rallies.
“Do you miss me?” Trump asked at a June gathering in Ohio. The crowd responded with
cheers. “They miss me,” he concluded.
Starts and Stops
If 2021 hinted at Trump’s continuing influence within the Republican Party, the 2022 midterm elections confirmed it.
By then, American military forces had haphazardly withdrawn from Afghanistan, leading to the fall of that nation’s US-backed government. Gas prices and inflation were approaching highs not seen in decades. US economic growth, which had been bouncing back from pandemic disruptions, sputtered. Biden’s approval ratings tumbled into negative territory. The political environment that had seemed so hostile to Trump at the beginning of 2021 was starting to shift.
Mar-a-Lago became an obligatory stopping point for any conservative candidate seeking to become their party’s nominee. The former president’s endorsement was the most coveted prize – a key to unlocking fundraising dollars and grassroots conservative support. Four of the six Republican House members who voted for Trump’s second impeachment and were running for re-election were defeated by Trump-backed candidates in party primaries. Meanwhile, Senate candidates like J.D. Vance in Ohio and Herschel Walker in Georgia pulled ahead in crowded primary fields with the help of Trump’s support. It began to look like his endorsement all but guaranteed a primary victory.
But if the first half of 2022 was unambiguous good news for the former president, November’s elections painted a much different picture. Of four prominent Trump-endorsed Senate candidates, only one – author turned politician Vance – defeated his Democratic opponent. While Republicans narrowly regained control of the House of Representatives, elevating Kevin McCarthy to the speakership, the party largely underperformed, and Democrats retained control of the Senate.
In Florida, Governor DeSantis, the distant second-place finisher in that 2021 presidential straw poll, won a surprising double-digit re-election victory, fueling speculation that he might actually be the real frontrunner for the 2024 Republican presidential nomination.
Meanwhile, Trump fumed – blaming the Republican shortcomings on the party’s support of unpopular abortion restrictions and insufficient fealty to his own brand of conservative populism. Only a few weeks after the midterms, when pundits were still wondering if the former president’s political moment had passed, Trump formally launched his 2024 presidential campaign.
Pathways to Power
The start of his presidential bid seemed shockingly ill-timed. Just a few weeks after the Republican midterm misfire, it put the former president in the headlines when many were still wondering if he had lost his political instincts. His formal announcement, held within the exclusive confines of Mar-a-Lago, made his campaign feel insular and ill-suited to the current political realities.
He would subsequently make news for all the wrong reasons - dining at Mar-a-Lago with Nick Fuentes, a prominent white nationalist, and posting on social media that rules in the US Constitution should be “terminated”, allowing him to be re-instated as president were all strangely dissonant actions that put him on the very fringes of political thought. The Thanksgiving through New Year period was a pretty dark time on the Trump campaign as more conventional Republicans were having their doubts and wringing their hands both in front of and behind the cameras.
The prevailing sentiment among those GOP nervous nellies seemed to be: “He's announced that he's running for president but are we sure that he's going to be able to pull this off?” This would be followed by the inevitable perennial question about the notoriously short attention span Trump had become known for: “Does he actually have the discipline to do this?”
People were not giving Trump enough credit. He has always been a wily, street-smart operator who learns by experiencing life, not through dusty theoretical texts. His 2016 presidential campaign was in truth a ramshackle, ad-hoc affair created not with the intent to win, but as a marketing tactic designed to give him and his businesses maximum visibility. 2020’s effort was better organized, but ultimately undermined by a sycophantic team more dedicated to pushing their own agendas then Trump’s.
By 2024, stung by losing to Biden, Trump assembled a behind the scenes campaign team that – unlike 2016 and even 2020 – was headed by seasoned political operatives. Chris LaCivita and Susie Wiles (recently appointed as the first female White House Chief of Staff) may not be household names, but the former was a bare-knuckled veteran of Republican politics with decades of experience and the latter had helped turn Florida into a conservative stronghold. They were, and are, smart, savvy, and most importantly, loyal to the boss.
The two worked with Trump to formulate a presidential primary strategy built around the candidate’s greatest strength: his marketing and messaging ability which in politics means capturing airtime aggressively by virtually any means so that the metaphorical airwaves are dominated by you. While DeSantis was bogged down with official duties in Florida, Trump moved early to define the contours of the campaign. And while others deferred to the Florida governor, Trump hit him head-on, demeaning and diminishing him.
Based on the establishment media’s anyone-but-Trump orientation, Ron DeSantis had been built up as a kind of Republican superman, at the very apex of politics with momentum behind him and couldn’t be torn down.
Trump tore him down with relentless attacks about his record, his character and most devastatingly of all, with a nickname: Ron De Sanctimonious.
Then came a boost from the unlikeliest of sources – prosecutors in New York, Georgia and the Justice Department in Washington, DC. Starting with the FBI search of Mar-a-Lago for sensitive national security documents in August 2022 and culminating in a series of indictments in 2023, the former president’s criminal jeopardy became a central issue in the rapidly unfolding Republican presidential nomination fight. Trump’s showman instincts capitalized on the moment: he wanted to be arrested, fully comprehending how incensed his base would be and how even his most vociferous opponents within the Republican party would be compelled to voice their outrage at what was perceived to be the weaponization by the Democratic administration of the US Attorney General’s office. His mugshot, glaring in a photograph taken at an Atlanta jail, was soon plastered on campaign t-shirts and yard signs: free publicity on a global scale.
For many on the increasingly histrionic left, justice was finally being served. But among the kind of conservative voters who choose their party’s nominee in early voting states like Iowa, New Hampshire and South Carolina, it became a moment to rally around their party’s embattled leader.
The indictments created a divide within the Republican Party between those who saw the indictment as an abuse of power and those who didn’t. Initially, Ron DeSantis took the ‘didn't’ approach DeSantis had at first called the March 2023 New York indictment, which he noted was about Trump’s hush-money payments to Stormy Daniels an adult film star, a “manufactured circus” that wasn’t a “real issue”.
By autumn 2023, Trump had opened a massive lead in most Republican primary polls – a margin he would never relinquish. He even skipped the Republican primary debates, depriving them of political oxygen. He focused instead on cementing support among rank-and-file voters through his trademark rallies and grassroots organizing. And soon DeSantis became political roadkill.
Despite raising nearly $200 million in campaign funds, DeSantis was out of the race within days of finishing a distant second in the January 2024 Iowa Caucuses. After Trump easily beat former South Carolina Governor Nikki Haley in New Hampshire, the Republican primary fight was effectively over. For the third straight presidential election, the party’s nomination was his.
Ups and Downs
The former president’s courtroom drama may have been a boon to his political fortunes, but it also came with very real legal implications. In May 2024, a Manhattan jury convicted Trump on 34 felony counts involving hush-money payments to adult film star Stormy Daniels.
In a pattern very similar to his business fortunes, every judicial setback, however, seemed to be followed by a bigger victory in much the same way that every bankruptcy was prelude to recovery. His sentencing was delayed until after the election, the document indictments in Florida were discarded, and the Supreme Court ruled that presidents have sweeping immunity for official acts.
Outside of court chambers, Trump’s campaign was rolling from his primary victory into the general election. A halting, hopelessly confused performance by Biden in his late June debate with the former president left Democrats in nothing less than a full-blown panic. At last, it appeared, the world was seeing what Trump had warned about all along: a blubbering, lost, bumbling, semi-senile incumbent.
Trump’s approval ratings and head-to-head polling numbers were ticking ever higher. And after his brush with an assassin’s bullet in Pennsylvania in mid-July (which he capitalized upon with his heroic, fist-pumping pose) he arrived at the Republican National Convention in Milwaukee a day later as nothing less than a conquering hero to his supporters and a feeling of inevitability to his opponents.
Tesla's Elon Musk, the richest man in the world, publicly endorsed the former president and began funding a massive organizing operation in key battleground states. Republican pride – pride in Trump – was running high and the party appeared more united than ever. It felt and looked like a campaign with momentum.
At that moment, it seemed like Trump’s return to the pinnacles of American power from the depths of 6 January 2021 was all but complete. A campaign that had first vanquished DeSantis and his other Republican rivals was now set to deliver a knock-out punch to Biden and the Democrats. There was even talk of an electoral landslide on a Reaganesque scale.
But, in a twist of fate so common in Trump’s biography, three days after he formally accepted the Republican Party’s presidential nomination, Biden abandoned his re-election bid and endorsed his vice-president, Kamala Harris. In a matter of a few weeks, Harris consolidated her party’s support, injected new enthusiasm into Democrats and even pulled ahead of the former president in some head-to head polls, buoyed by the halo effect of “newness.”
Trump’s efforts were not helped by a scattershot and frankly, occasionally surreal debate performance against Harris in September (the less said about animal-eating immigrants the better) and an apparent difficulty reorienting his campaign to take on his new opponent, whose strengths – and weaknesses – were decidedly different from Biden’s.
Yet this also afforded him an opportunity not remarked upon by observers and pundits. Donald Trump is usually not at his best until he is tested, and his competitive streak fully engaged. After some floundering and obvious testing of attack lines and sound bites, Trump began to find his footing back. Harris, seeking to channel Barack Obama’s magic, did not build upon the almost hagiographic coverage of her convention performance by seeking to define herself, her policies and her convictions. Instead, she coasted along on ephemera like good feelings, hope and change, allowing Trump the breathing room to retool his message and hit her back with accusations of socialist, even communist tendencies.
Most tellingly, he sprinkled his occasionally outrageous attacks with pointed segues into bread-and-butter issues like the economy, the cost of living, inflation, followed by attacks on Biden/Harris’s record on illegal immigration, the porous border and the administration’s seeming inability to end the crises in the Ukraine and the Middle East. For their part, the Democrats responded by not allowing Harris to contrast her policies with Trump’s but rather to concentrate her fire on Trump by name-calling and essentially threatening the end of democracy and hellfire if he were to prevail.
They ended up on his playing field. No one can out-insult Donald Trump: she sounded alarmist and shrill’ He was a known commodity after his three runs at the White House; she was a cipher spouting platitudes and bromides. He connected with blue-collar workers while serving French fries at McDonald’s while she hobnobbed with celebrities. She talked about issues orientated more towards college-educated urbanites in high-flown theoretical language while he spoke in clipped terms blue-collar workers understood. She had trouble reconstituting the Obama coalition because she simply did not have the charisma or the policy heft while Trump ultimately won mor African-American and Hispanic votes than any previous Republican nominee in the modern era.
As 2024 comes to its end, Trump has been in the whirlwind of presidential politics for nine years now – and in the public spotlight for more than four decades. He has seemed indefatigable. But with another four years in the White House looming on the horizon, what is likely to come?
Realignment and Transformation?
That Trump simply got this close to the prize once again was a remarkable achievement. And now he will return to the White House having overcome obstacles – legal, political, many of his own creation – that few presidents have confronted.
With control of the reins of power, the majority in the Senate (and as of this writing) possibly the House, and without the burden of having to face the judgement of voters again, Trump will be able to make those legal dangers disappear. And unlike his first term, he will be entering the White House with a team of advisers and administration staff who are fully loyal to him.
His intent to dramatically reorganize the federal bureaucracy could replace career civil service employees with political acolytes. And even if he doesn’t win full control of Congress, he could use existing presidential powers to impose new restrictions on immigration, enact his plans for mass deportation of undocumented residents and impose tariffs that are designed to protect US jobs but could significantly increase the cost of imported goods, not to mention affect inflation, severely curbing the fiscal room to maneuver for many countries.
Democrats warn that this would be a presidency without “guardrails” to limit what they say are Trump’s more dangerous proposals. Republicans, in a party that has been remade in Trump’s image, hope that he will be able to more effectively enact his agenda without the internal resistance and organizational chaos he faced in his first term.
For a man who has always seen himself as larger than life, the hero of his own story, and with a burning desire to leave his mark on history, Donald Trump, the King of the Comeback could fundamentally reshape American government for generations to come.
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