These problems—the fractious staff, the vast range of distractions, the press battles, the machinations of other stakeholders, and the gusher of leaks—pose a special challenge to Trump because they are features of the political world that are distant from the way he was able to run his company in the private sector. Businesspeople aspiring to public office have for years argued that their experiences in the private sector will make them effective in the public sector, only to find that the two realms reward and require different, if overlapping, skill sets.
For Trump, the shift is partly a matter of size: The Trump Organization, despite its large declared assets, is a lean company with a small, tightly-knit staff, with family members as executive staff—a mom ’n’ pop that runs international resorts, basically— while Trump now sits atop the massive, sprawling federal bureaucracy.
Galston believed Clinton, the longtime governor of Arkansas, had a similar problem adjusting to the scale of the federal government: “What’s typical about talented governors of small states is that they are head and shoulders above the other politicians in their state, and they can—through force of intellect and character and a loyal dedicated staff—move the political system of those states… Washington is not that way at all.”
But Trump’s challenge is also structural. In business, Trump was constrained only by his deal-making abilities and, to a certain extent, regulation and the law—though he showed an affinity for sidestepping regulations and civil suits through lengthy litigation and creative settlements. Government’s lattice of checks and balances is already hobbling Trump; when the federal judiciary suspended his immigration executive order, he lashed out in anger.