Theodore Roosevelt vs. Donald Trump
Lessons of history for Trump's second administration
Echoes of the Gilded Age
Many political observers have noted striking similarities between today’s political climate and the Gilded Age (1870 – 1900). Democracy’s Sisyphus previously argued that the de-exceptionalization of American politics would feel more familiar to voters at the turn of the 20th century than to those of the post-war period. The Economist recently compared Donald Trump to President William McKinley. However, most Trump supporters would likely find a McKinley-style presidency underwhelming. Who they truly want is McKinley’s successor—President Theodore Roosevelt.
Roosevelt is often called the first modern president because he wielded executive power more broadly than almost any of his predecessors and shaped the United States’ political identity more than any president before him. There are indeed similarities between Roosevelt and Trump. Much like Trump mastered social media to advance his political agenda, Roosevelt was the first president to leverage large-circulation newspapers—the social media of the Gilded Age—to his advantage.
Despite his privileged upbringing, Roosevelt had an uncanny ability to connect with and articulate the frustrations of the “common man.” He was no stranger to hyperbole and occasional name-calling. He famously derided McKinley for having “no more backbone than a chocolate éclair,” and his political agreement with Senator Mark Hanna allegedly included a promise to stop calling him “old man.” Like Trump, Roosevelt was not lacking in ego. His daughter Alice once remarked that he wanted to be “the bride at every wedding” and “the corpse at every funeral.” However, crucial differences separate Roosevelt from Trump and these differences tell us a lot about both men.
The Men Off the Stump
Roosevelt did not rise to power through reality TV fame or a series of failed business ventures. By the time he became the youngest president in U.S. history, he had already served as a state legislator, Civil Service Commissioner, Police Commissioner, Assistant Secretary of the Navy, Governor of New York, and Vice President. That was in addition to his combat service and status as a bona fide war hero.
Roosevelt was also a scholar and writer. Before and after his presidency, he authored works on an astonishing range of topics. His biographer, Edmund Morris, observed that what seemed like impulsiveness from Roosevelt often stemmed from his mind simply moving faster than those around him. Roosevelt read, on average, a book a day, making him perhaps the most well-read president in U.S. history. As Morris wrote, “Theodore in private was different from Theodore on the stump.” His habit of “charging arguments with more passion than needed” led some to forget that he was “actually a thoughtful man.”
Thoughtfulness is not a characteristic typically associated with Trump. His decision to pardon over 1,500 January 6 perpetrators reportedly caught even some of his closest advisors off guard. Reportedly, the decision was reached in a discussion where Trump simply declared, “F--k it! Release ‘em all.” Accounts from former Cabinet officials, along with books’ worth of late-night social media posts, cast doubt on any claim of deep reflection. The Republican Party as a whole seems to have abandoned scholarly thinking, replacing it with conspiracy theories as the pseudo-intellectualism of the right.
Commitment to Order and Rule of Law
Roosevelt’s presidency demonstrated his consistency in progressive beliefs. He pursued change where necessary but always viewed the government’s highest role as maintaining order and promoting the general welfare. He enacted meaningful reforms but never sought to create chaos.
Crucially, Roosevelt had a genuine commitment to the rule of law. His famous Square Deal was not just rhetoric—it was a true governing principle. As The Economist pointed out, McKinley had the backing of the industrial titans of his day, most notably J.P. Morgan. That support, somewhat reluctantly, shifted to Roosevelt after McKinley’s assassination.
Morgan was stunned when Roosevelt and his Attorney General filed suit against him, launching the trust-busting era. He met with Roosevelt, incredulous that the issue had not been settled privately. Why had they not just made a deal? Morgan asked. Roosevelt rejected the notion but assured him that the government would not arbitrarily target his other interests unless wrongdoing was found. Roosevelt genuinely believed the trusts violated the law and harmed the common welfare—but he also believed that even the wealthiest Americans were entitled to a Square Deal. The United States government was not just another business rival with whom to negotiate.
This contrasts sharply with Trump, who insisted TikTok should be banned until a wealthy Trump donor had important connections to the company—after which he suddenly became open to working out a deal. Similarly, he initially dismissed cryptocurrency but embraced it once he personally profited from it. The contrast is further underscored by the billionaires who once opposed Trump but have since donated heavily, seemingly hoping to avoid being “DOGE’d.” Meta and CBS have both chosen to settle lawsuits they were embroiled in with President Trump. The latter reportedly did so to avoid getting a desired merger blocked by the administration. President Trump has proven almost conclusively that he isn’t just someone with whom you can make a deal, he is someone with whom you must make a deal.
The Roosevelt Administration vs. the Trump Administration
Although Trump likes to talk about the “historic” nature of his victories they are not, mathematically speaking, historic. Roosevelt’s landslide victory in 1904—56% of the popular vote and 70% of the Electoral College—remains unmatched by any president since Ronald Reagan. By 1908, his reelection was all but guaranteed, yet he chose to honor democratic norms and step aside. Biographer Edmund Morris identified this as one of Roosevelt’s proudest achievements. Despite his expansive use of executive power, Roosevelt still recognized the necessity of restraint. Maybe because he could see the danger in himself.
That restraint extended to those around him. Elihu Root, who served as both Roosevelt’s Secretary of War and Secretary of State, was no lackey. He was far less progressive than Roosevelt and had helped arrange Roosevelt’s meeting with J.P. Morgan. He was a competent, independent-minded official, and Roosevelt valued his counsel. Roosevelt never demanded personal loyalty, ideological purity, or adherence to conspiracy theories. Despite their ideological differences, he still called Root “the ablest man… in government service” and hoped he would succeed him as president.
No Elihu Roots exist in Trump’s orbit. His first administration had a staggering 92% turnover rate among senior officials. His second term is unlikely to be different. Even Vivek Ramaswamy, who was never officially part of the Administration, found himself discarded after an errant tweet. Former “A-team” members quickly transformed into imbeciles the moment they departed. Quick turnover and the treatment of those dismissed send a clear signal that Trump does not want to be challenged.
Another key difference may have nothing to do with Roosevelt but resides with Congress. When Roosevelt assumed the presidency, the legislative branch was still jealous of its power as the founders had intended it to be. With a House run by “Uncle Joe” Cannon, perhaps the most powerful Speaker in history, and Senators like Henry Cabot Lodge and Mark Hanna controlling the Senate, they were far from a rubber stamp for Roosevelt, nor did he expect them to be. In particular, his attempt to reform the military into a modern fighting force more capable of projecting power abroad was not always well received by his fellow Republicans.
Despite these challenges, Roosevelt worked within the system rather than against it. He sought bipartisan support for his initiatives but never demanded absolute loyalty from his party. He did not attempt to purge dissenters or brand them as enemies. No RINOs to be shamed and castigated. Had he tried to for conformity, it would surely have been rejected by powers within his own party.
Democracy’s Sisyphus has already written about the damage done by an ineffective legislative branch that continually avoids its duty. That does not show great signs of improving under Trump. Partially because he isn’t keen to see it happen. Today’s Republican-led Congress, rather than asserting its constitutional role, increasingly defers to the executive branch. Instead of reclaiming authority from bureaucratic agencies, many lawmakers seem eager to transfer more power to the president. For example, Senator Mike Lee’s recent push to make it so the President doesn’t have to spend money allocated by Congress. Overturning Nixon-era laws. Effectively attempting to forfeit the power of the purse to the president.
Roosevelt contended with a legislative branch that valued its independence and refused to cede its authority. Trump, in contrast, faces a Republican majority that shows little interest in countering a strong executive. If Congress continues to sideline itself, it will further erode the checks and balances that have long defined the American system.
The 1912 Roosevelt: A Warning from History
Frustrated by Taft, fueled by ego, and egged on by frustrated progressives, Roosevelt entered the most Trump-like era of his public life in 1912. He ignored the pleas of those who had once restrained him, including Root, and attempted to regain the presidency. This unrestrained Roosevelt, surrounded by only his most fervent followers, embarked on a Quixotic quest to gain the Republican nomination.
His campaign for the Republican nomination became a personal crusade, filled with vitriol and a messianic tone that far exceeded anything in his earlier political career and anything that came after it. He championed increasingly radical ideas, such as subjecting judicial decisions to the popular vote. When the Republican Party denied him the nomination, he declared the process fraudulent and took the party down with him.
Even as an admirer of Roosevelt, it is hard to read this chapter of his history without being awestruck by his zeal and political will—while also concluding that this version of Roosevelt was unfit for office. Ultimately, his former allies saved him from himself by ensuring his defeat.
Conclusion: Strength Without Restraint is Weakness
In his years as president, Theodore Roosevelt embodied a nuanced approach to strong executive leadership. Championing government intervention where necessary while maintaining a deep respect for democratic principles and the constitutional structure. He never sought to undermine the peaceful transfer of power or consolidate authority in ways that disrespected the legislature’s prerogatives. Roosevelt was undoubtedly a man of ambition and ego, but these traits were tempered by intellectual curiosity and a respect for the institutions of government.
The United States has endured turbulent and erratic presidencies before, but for the good of the country—and even for the good of Trump himself—Republicans must reintroduce restraint. Otherwise, they risk engaging in what William Allen White accused the GOP of in 1912:
We made the too obvious pretense in those days of our party loyalty…Whistling in unison through the tall timber of darkening events to support our courage.
