On first glance, it might be unexpected to compare Omaha from a century ago to the reality of the United States right now. However, there are lessons to learn about Tom Dennison (1858-1934) and Donald Trump, the current president. This article compares their reigns and gives a new light on what the history of Omaha can teach the entire country today.

The Men at Hand

Tom Dennison was an old world political boss who ruled Omaha from the shadows of its saloons. Trump is a modern-day populist who commands the world stage from a perch of national and global media. There are strange and enduring threads that connect both of these men. While their eras and arenas of power are a world apart, the methods they employed to seize and keep their influence reveal a shared playbook that spreads across the boundaries of time and technology.

Both men were masters of manipulating the public by bypassing traditional media to control their own narratives and discredit opponents. They both built political bases less on ideology and more on a “cult of personality.” This fostered fiercely fealty among their followers that prioritized their leadership over established institutions, party platforms, and the democratic processes they controlled. Ultimately, both Dennison and Trump are seen as figures who used powerful populism and divisive rhetoric to climb and “succeed” in their whims.

Let’s unpack those realities.

The Art of the Outside Man

Both Dennison and Trump were masters of being outsiders. Dennison, with his gambling debts and no formal education, was the quintessential anti-establishment figure in Omaha. Positioned as a man the people who battled against the city’s blue-blood elite, Dennison wasn’t a politician. Instead, he was a strongman who fixed things for his people, always speaking in blunt ways that resonated with those who felt abandoned by the system.. Trump, in his own time, has cultivated a similar image by framing himself as a champion for the working class and a disruptive force against a “corrupt” establishment in Washington, D.C. Neither figure climbed up through the party ranks to become a boss. Instead, they both went past the old gatekeepers and built direct, transactional relationships with their bases.

One of the main keys to these relationships was the strategic control of the narrative. Dennison’s machine had a close alliance with the Ed Rosewater, the publisher of the Omaha Bee and a Republican Party operative of the times. That newspaper was Rosewater’s own personal mouthpiece, spinning stories and discrediting enemies with all the time, without hesitating. It was a 20th-century prototype of narrative manipulation. In the 21st century, Trump has achieved a similar effect, not through a single outlet, but by using the full force of social media and a mastery of the news cycle to bypass traditional media and speak directly to his followers, often casting doubt on any information that challenges his version of events.

The tools changed, but the tactic remains the same: The one who controls the story controls the people, and the one who controls the people has the power.

Power and Its Pervasive Reach

At that point though, the stories of these two become pretty different.

Dennison was a political boss who built his empire on peoples’ vices, including gambling, prostitution, and bootlegging. He never held public office, instead acting like a shadow government. He was propped up by patronage and the ability to swing elections by simply delivering a block of votes, including the Irish, Black people, the Czechs, and others. Omaha was his own private world, and his operations were purely transactional. Dennison used his power to protect his crime syndicate and punish his enemies, often ruthlessly.

By contrast, Trump’s power is apparently formal and constitutional. He ran for and won the nation’s highest office twice, revealing his own biases and discriminations with intention in order to manipulate the electorate and divide his opposition. He has assumed extralegal authority of the presidency by suppressing the power of the Congress and the courts. His influence is not rooted in a localized patronage machine but in a national, decentralized movement built on charisma, media, and direct appeals to a his base. By nearly constantly challenging democratic norms, his power operates outside of the established framework of the American republic, he imposes his will by manipulation and misdirection. While this is different, its not completely opposite from Dennison’s back-alley governance.

This differences in scope and legality are undermined by the crucial similarities in how each figure used division to their advantages. Dennison was a direct and tactical inciter of racial hatred. His machine, as we know from historical accounts and grand jury findings, deliberately instigated the 1919 Omaha Race Riot to discredit a political rival, which resulted in the lynching of Will Brown and the segregation of Omaha’s African American community. It was a cold, calculated move of a political boss using a lynch mob as a weapon to remove his enemy, and was a specific and direct cause-and-effect event. Trump’s rhetoric has long fanned the flames of social and racial division and he was found to be directly responsible for events like the January 6, 2021 Capitol riot. His involvement in such events is of a similar nature to Dennison’s involvement in Omaha—one of clear and direct tactical orders to remove a political rivals from their offices and popular opposition from democratic involvement.

Reconsidering Relevance

The end of Tom Dennison’s power and Donald Trump’s current popular standing are similar. Despite facing huge public and legal pressure, both men retained a core group of deeply loyal supporters.

At the end of his run, Dennison’s machine was fatally wounded by a public trial that exposed its corruption in many ways, and it ultimately dissolved upon his death. Trump’s influence, while also facing legal challenges, has proven more resilient, as his brand and direct connection with his base are a powerful force in politics right now. If anything, he shows how Dennison could have shifted from a localized, patronage-based machine to a national, media-driven political horror show. The words of both men have real-world consequences that contribute to social discord, political unrest, and the destruction of democracy in real time.

In the end, Dennison and Trump tell us two stories about power with one single emphasis. Dennison’s is a story of how a man can subvert a city from the outside by using fear and patronage. Trump’s is a story of how a man can master a nation’s own institutions and media to control the public. These two stand are peculiar historical bookends, each a testament to how charisma and control over the narrative can reshape a political landscape, whether that landscape is Omaha or the entire world.

Special thanks to my friend Wendy for recommending I write this.

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