Bully Power: How Teddy Succeeded and Trump Failed.

Charlie Kirk in The Federalist recently compared Donald Trump and Grover Cleveland, likening the 2024 election to the 1892 election between Cleveland and Benjamin Harrison. However, while the circumstances between the elections were similar, Trump and Cleveland are very different people. Trump, a dynamic and active communicator, contrasts with Cleveland, who was more passive in his approach. While Cleveland had no real ambition to be president, it has been the apple of Trump’s eye since before his days on The Apprentice.

Cleveland was a diligent executive. He operated with honesty and integrity—a steady hand on the executive lever of power in a time of corruption and division. Trump, on the other hand, was an impetuous executive. He operated with hostility and crassness. A drunken captain spinning the wheels of power on a joy ride. While Cleveland bridged the gap between corruption and division in his time, Trump drove a wedge between his supporters and the Republican party.

Trump is more like another Gilded Age president, Teddy Roosevelt—both wealthy New York aristocrats who executed bully power. While Cleveland operated the executive branch as a negative check, using the veto and limiting federal power, Trump and Roosevelt operated as progressive positives, legislating executive orders and expanding federal power. However, Trump differs from both Cleveland and Roosevelt. While the latter saw their power as a responsibility and sought to check the corrupting forces that led them there, Trump saw power as his spoils and rewarded the corrupting forces that lifted him.

Roosevelt and Trump's cult of personality is the source of their bully power. However, Roosevelt’s power was scaffolded by a sense of duty and honor, hard work and diligence, and Trump’s from a sense of privilege and ego. While Roosevelt “spoke softly and carried a big stick,” Trump spoke loudly and carried a twig.