It would be hard to fashion a more exquisite snare for a man like Donald Trump than the modern, institutional presidency. Just five months into his term, he appears trapped by its constraints—and the harder he tries to escape them, the more thoroughly entangled he becomes.

On Thursday morning, President Trump again lashed out at the “bad and conflicted people” investigating him for obstructing justice. “They made up a phony collusion with the Russians story, found zero proof, so now they go for obstruction of justice on the phony story,” he tweeted. But to take Trump’s charge at face value is to read it as an indictment of his own blunders. Trump is claiming that there was no underlying wrongdoing, but his decision to fire his FBI director sparked the appointment of a special counsel who’s now exploring whether it was a criminal act. This, he says, is a purely self-inflicted wound—or, as a senior administration official told The Daily Beast, “The president did this to himself.”

Trump is, in many ways, a man out of his time. He ran his business as he is attempting to run the presidency, as a 19th-century style entity, built around its proprietor. But the federal government has long-since evolved into a modern bureaucracy, an institution Trump appears to have neither the experience nor the patience to successfully operate.

Trump’s business empire sprawls into hundreds of LLCs and licensing agreements, but at its core, it takes a familiar form: the proprietary firm. Built around its founder, generally branded with his name, its reputation intertwined with his, and its affairs directly under his management—this was the dominant form of business in the United States until the final decade of the 19th century.  

There are real advantages to that arrangement. It confers flexibility, allowing leaders to react to shifting circumstances with speed, and to take risks without fear of being second-guessed. It mitigates the agency problem—the danger that professional managers will prioritize their own interests. And to the proprietors, it offers the satisfactions of independence; they control their own destinies.

It is a form almost perfectly adapted to play to Trump’s strengths, and cover his weaknesses. As a CEO hired by an independent board, he might not have survived the bankruptcies of some of his businesses, a string of failed ventures, constant lawsuits, or the other setbacks of his career. But the Trump Organization is his to do with as he pleases, and if not all the risks he chooses to take, the loopholes he exploits, the deals he strikes, or the ventures he launches have succeeded, enough have paid off to preserve and expand the fortune he inherited.

But America is now a century or more past its managerial revolution—the heyday of the proprietary firm is gone, displaced by the corporate bureaucracy. It swept through industry in the Great Merger Wave at the turn of the 20th century, and through the federal government in the decades that followed. Bureaucracies offer a solution to the challenge of scale; they create rules and procedures, and the corps of professionals who populate bureaucracies abide by them, allowing business to be performed in a predictable fashion, even between actors with no personal relationship. And they bring with them their own set of costs and benefits, requiring the surrender of a degree of autonomy and flexibility in exchange for stability and scale, and putting systems ahead of individual initiative.

The presidency itself underwent a similar transition. In the 19th century, as the historian Brian Balogh has argued, it was already tremendously powerful—but operated indirectly, through third-party entities like state and local governments. It was a great deal like the Trump Organization—a relatively small staff, multiplying its influence by striking deals with larger entities that had the personnel to put its plans into action. As late as 1900, William McKinley had just 13 staffers working directly for him in the White House. Today, the Executive Office of the President claims more than two thousand personnel; the federal government, more than two million.

It is a world against which Trump seems to rebel at every turn. He refuses to empower his chief of staff to create a rule-bound White House, preferring instead to pit advisers against each other in a more freewheeling style. He insists on reaching directly down to subordinates, instead of moving through the hierarchy—calling the acting head of the National Park Service to complain about a photo, tweeting his defense of his travel ban instead of issuing statements through his press office, and meeting with the FBI director instead of the attorney general.

And each time, he has only worsened the trouble he sought to address, or created new problems for himself—producing mockery of his exaggerated crowd-size claims, court injunctions against his executive orders, and now an investigation for obstruction of justice. His repeated defeats seem only to deepen his anger as he strains against bureaucratic rules, the thousands of Lilliputian strings that not even presidential giants can snap.

There is no better example of this than the memo, that humblest—most spare and restrained—of literary genres. It was born in early modern Europe, but came of age during America’s managerial revolution, a key technology of the administrative bureaucracy. They institutionalized memory, making decisions legible to those not personally present, and creating records of conversations that could be referenced later by other bureaucrats.

In the process, they became the key tool of bureaucratic warfare. As MIT’s JoAnne Yates wrote, in her history of the memo as a managerial genre, “This extension of documentary communication also reflected more specific political motivations. As companies grew, allegiances to and rivalries between departments created friction, and each side of each dispute wanted to document its view of the issue.”

When Trump breached protocol and met alone with Comey, the FBI director went back to his office, and wrote a memo. When Trump called NSA Director Mike Rogers to criticize the intelligence community’s conclusions on Russian interference and to pressure him to publicly disavow the possibility of collusion, The Wall Street Journal reports, the NSA’s deputy director dutifully recorded it in a memo. There’s no indication the president ordered his own staff to document his view of these conversations. His preferred form of written communication to subordinates is the personal message scrawled with a Sharpie, not the memorandum dictated to file.

Memo to the president: You’re losing this game because you don’t understand its rules.

There’ve been no shortage of op-eds and talking heads telling the president that he disregards the institutional constraints at his considerable political and legal peril. Many White House advisers have reportedly told him the same, even as others have egged him on. But Trump obtained his clearest warning of all from the man from whom he was least inclined to receive it.

A week after Trump’s election, President Obama held a news conference. He was asked, among other things, about his handling of detainees in Guantanamo Bay. “Keep in mind,” he replied, “that it's not just a matter of what I'm willing to do.” Obama was no minimalist when it came to executive authority; he had pushed the powers of his office further than any of his recent predecessors, often in ways that federal courts would later strike down for exceeding his authority, or failing to follow prescribed bureaucratic procedures. And along the way, he had been humbled to discover that there are limits to what a president can achieve through sheer force of will and disregard of precedents.  

“One of the things you discover about being president is that there are all these rules and norms and laws and you've got to pay attention to them,” he continued. “And the people who work for you are also subject to those rules and norms. And that's a piece of advice that I gave to the incoming president.”

Maybe it’s a lesson each president needs to learn for himself.