Toast to the Plan Trusters

An unparalleled comeback we will never see again

It was impossible to imagine in January of 2021. The entire online world had exiled him, and the political system impeached him and hid him for two weeks. If you were in Washington anytime that winter and spring, the mix of homeless encampments and fencing in the heart of D.C. was depressing. Despite this banishment, Donald J. Trump is now, four years later, the president of the United States of America.

In American history, political comebacks are few and far between, showcasing the resilience of peculiar politicians. Failed comebacks in both parties litter 21st century history: Spitzer, Weiner, Clinton, Sanford, and Jeb. While Donald Trump's return to the presidency is unique in many ways, there are parallels to others who staged high profile comebacks. Is Trump’s path so different? We know other comeback stories, but is anyone on his level?

One of the most famous political comebacks in American history is that of Richard M. Nixon. After losing the presidency to JFK in 1960 and a gubernatorial race in California in 1962, his political career appeared over. He was young though and brilliant. It is forgotten how he and JFK were both incredibly young in 1960 (47 and 43 respectively). In 1962, he famously declared at the concession press conference, “You won’t have Nixon to kick around anymore.” The Sixties went awry though as Camelot crumbled and the dream turned into a nightmare. Nixon meticulously rebuilt his political image over the next few years, capitalizing on divisions within the Democratic Party, supporting safe but new GOP congressional candidates and focusing on the growing concerns about Vietnam (read Nixonland). In 1968, Nixon won the presidency, positioning himself as a stable leader capable of addressing the nation’s challenges during a chaotic era and using advertising that removed Nixon from the ad and focused on broad, American problems (read The Selling of the President 1968). Nixon reached the top, but his first peak was not as high and his low was not as low as Trump’s.

Grover Cleveland’s comeback offers another striking parallel. Cleveland was the first U.S. president to serve two non-consecutive terms, winning in 1884, losing in 1888, and winning again in 1892. His political resilience was rooted in his adherence to principles and a reputation for honesty. Similar to Trump, he was fighting corruption. After his defeat in 1888, Cleveland maintained a significant connection to the Democratic base and benefited from public discontent with the Republican administration of Benjamin Harrison. Cleveland’s loss was also a rare case of the popular vote victory/electoral college defeat combination. Cleveland’s return to the presidency was a testament to his enduring appeal as a fighter… and Harrison’s billion dollar spending spree that angered voters. That feels Trumpish but not quite.

President Cleveland is a bit too deep in the past. The wilderness period matters for Trump’s journey as well. Governor Jerry Brown’s political path offers insights into political comebacks. Brown served as governor of California from ‘75 to ‘83 as a progressive and unconventional leader who capped property taxes when Prop 13 passed. After leaving office, Moonbeam unsuccessfully ran for president as an old, retread lib in ‘92 to stop moderate Clinton and faded from the political spotlight. It was insane to see Brown resurrect his profile and in 2010, a full generation after his first governorship, Brown returned to California politics, winning the governorship again. His comeback was fueled by the Democrats having no good bench in California, the state’s economic challenges after the housing crash, and his ability to position himself as an experienced leader. California had moved so far left that he was moderate now. Brown’s resurgence misses a little flair though, someone else has what we are looking for.

Let’s go back to D.C. The story of Marion Barry in Washington, D.C. stands out. Barry, the mayor of Washington, D.C., from ‘79 to ‘91, was caught on camera smoking crack (“The bitch set me up.”) and presided over a crime infested dump. Barry retained strong support among many core D.C. constituents, particularly the black community. In ‘94, he staged a remarkable comeback, winning re-election as mayor after the arrest. Barry’s return relied on the rather unique connection between a black mayor and majority black city, so it taints the comparison to Trump even if it has a criminal element.

President Trump’s comeback shares some similarities with these examples, yet stands apart in profound ways. Like Nixon, Trump has faced a wilderness period as an outsider sentenced to political exile, but retained a devoted base. Similar to Cleveland, he is one of two presidents in U.S. history to serve non-consecutive terms. Like Brown and Barry, Trump has leveraged his status as a known political entity to restore an older order. Trump’s comeback bid is occurring in an unprecedented media and political environment, marked by intense polarization, the dominance of left wing influence in legacy and social media, and lawfare from coordinating state and federal entities.

What makes Trump’s attempted comeback unique is the scale of his influence within the Republican Party and the broader political landscape. Unlike Nixon or Cleveland, who operated within established norms of party loyalty and governance, Trump was an outsider who reshaped the Republican Party with MAGA. His ability to maintain a strong grip on the party, even after losing the presidency and multiple indictments, speaks to his unparalleled connection with a chunk of the electorate. This loyalty has allowed him to remain the central figure in American politics, despite efforts from opponents to sideline him. We cannot forget that after brushing aside legal setbacks and a lame primary season, someone came within a half an inch of killing him.

Trump’s comeback is unfolding amidst unprecedented challenges, including multiple criminal indictments and civil suits intended to bankrupt him. No major presidential candidate in U.S. history has faced such legal scrutiny while running for office with the added concern of two assassination attempts. Assassinations stymying political dreams is deeply ingrained in the American psyche for the mass media era. President Trump managed to survive. Trump framed these challenges as evidence of political persecution has energized his supporters and reinforced his narrative as a political outsider fighting against the establishment (the murky ‘they’). His return not only defied historical precedent but also signifies a broader transformation in American politics, where traditional norms and barriers no longer apply.

The spectacle matters and his 2025 inauguration delivers on it. He signed EOs as part of a rally. Made a rock star type appearance for his fans. EOs were being signed continuously as he fielded questions from the media. It was all a show, and the end to a chapter in the greatest political story ever. The next chapter opens with the return of the king and a public no longer hiding their MAGA hats in closets.

While American political history is rich with examples of remarkable comebacks, President Trump’s January 20th, 2025 return to the presidency stands alone. His return to the throne, despite unprecedented legal and political challenges and despite scheming assassins, highlights the shifting dynamics of political coalitions and media power in the age of realignment. No one before Trump has ever come back from such setbacks, and no one after Trump ever will.