Grover Cleveland and Donald Trump are two presidential phoenixes rising from the ashes of electoral defeat. But in the land of second chances, some sequels are best left on the cutting-room floor. Cleveland’s second act was a tragedy in four years, a cautionary tale the GOP seems hellbent on remaking, this time with more hairspray and fewer facts.

In 1892, Cleveland, like Trump in 2024, was resurrected by unwavering party loyalty despite losing the previous election. Both men, separated by time but united in their disdain for the “establishment,” demanded fealty with the fervor of medieval kings suffering from lead poisoning.

But the true test of a leader comes not from an audacious encore but the improvisation when chaos reigns. When faced with national crises, their ability to pivot was akin to that of the Titanic avoiding its infamous iceberg — tragically nonexistent and disastrously consequential. 

For Cleveland, a Democrat, it was the Panic of 1893, a severe economic depression triggered by railroad overbuilding and shaky financing, which set off a series of bank failures. Within months, unemployment skyrocketed to nearly 20%, over 15,000 companies and 500 banks failed, and farmers in the South and Midwest faced ruin as crop prices plummeted. His inflexibility exacerbated the crisis as he rigidly hung on to the gold standard and fiscal conservatism, fracturing his Democratic Party. 

Trump, meanwhile, faced the Covid-19 pandemic with a mix of self-absorption and pseudoscience that would make snake oil salesmen blush. Trump’s erratic policy shifts on tariffs, immigration and foreign relations threaten to create both domestic and global chaos.

Despite their contrasting styles — Cleveland’s stubborn adherence versus Trump’s mercurial shifts — both approaches risk the same disastrous end: a party in disarray. Just as Cleveland’s policies led to William Jennings Bryan’s populist takeover of the Democrats in 1896, Trump’s volatility could trigger a schism between MAGA loyalists and traditional conservatives, fracturing the GOP coalition. 

Trump, at 78, would be the oldest president ever inaugurated. As we learned from President Joe Biden, the commander in chief’s age isn’t just a number; it can be a problem. While some argue that Trump’s base is unbreakable, history suggests that even the most seemingly unassailable political figures face internal challenges, particularly as they age. Their grip on power wanes. Why wouldn’t it? Trump’s glory days are likely behind him; Republicans need to chart a course for the future.

For Cleveland, the second-term midterms were a political bloodbath, ushering in nearly two decades of Democratic exile from power. In a stunning reversal, Republicans gained 130 seats in the House of Representatives, the largest swing in a midterm election in U.S. history, while also securing a 10-seat majority in the Senate. By 1896, Cleveland, 59, found himself a pariah in the party he once led.

If Trump’s second term is a disaster right out of the gate, his party may take a beating in the 2026 midterms. And it’s also not hard to imagine a third party capitalizing on widespread electorate cynicism toward Democrats and Republicans. After Cleveland’s presidency, the People’s Party (or Populists) briefly threatened the two-party system — until the Democrats absorbed them. As electoral cynicism reaches levels that would make Diogenes proud, the preconditions for a third party to find its footing might soon be complete. 

Comebacks can be pyrrhic victories, triumphs that contain the seeds of their own destruction. Cleveland’s presidency imploded in a shower of broken promises and shattered alliances. So, too, might Trump’s — and with it, the future of a party that has hitched its wagon to a reality star that may well be a supernova in disguise. The stage is set for a performance that could reshape not just Trump’s legacy, but the very foundations of the Republican Party. 

Will the GOP heed this historical cautionary tale before the midterms or are they doomed to star in a remake of a flop, hoping against hope that this time, the ending will be different? As the curtain rises on this improbable second act, one thing is certain: In the theater of American politics, the most tragic plays are often those we’ve seen before.