During the presidential campaign last year, it seemed at times that Donald Trump was as surprised as the governing and chattering classes when he surged to the lead in the Republican primaries and secured the nomination. During and after the convention, it also appeared to some that Trump was not intent on winning the election, given some of his actions and comments and the disarray of his election team, until Kellyanne Conway took over. This even led to speculation by some that Trump was an agent of the Clintons, convinced to run in a devious plot hatched by Bill to destroy the Republican Party and throw the election to Hillary.
Obviously, if there was such a plot, it failed hilariously and spectacularly, and only a conspiracy nut or a fool would hold to it today. But there may be a kernel of truth behind the idea that Trump did not really want or expect the presidency, as opposed to launching another fun (for him), ego-stoking, and publicity-garnering, if quixotic, executive run. Correspondingly, he might now regret the decision.
Compared with most other candidates, or anybody else, for that matter, Trump had little to gain by becoming president. He was already extremely famous, wealthy, and powerful. In terms of day-to-day comfort and luxury, the White House was a come-down, and let's not even discuss Camp David. Trump's preference for his Florida estate as opposed to the venerable presidential retreat is understandable, considering his circumstances.
In terms of management, the White House is a problem, too. As the CEO of a privately run company, Trump was effectively all-powerful – so much so that even creditors tended to dance to his tune. As president, he is only part of a triumvirate with two other co-equal branches. In the especially partisan environment that dominates American politics, getting anything accomplished is slow and tortuous at best, futile at worst. And Trump doesn't truly control the executive branch, either, which has grown to such monstrous proportions and has its tentacles into so many facets of daily American life that his direct influence over it is marginal.
Perhaps Trump's frustration has never been more evident than in his recent and controversial tweets concerning the status of his own executive order restricting immigration from certain Islamic countries. The tweets have been widely reported and are now well known. Trump reiterated campaign rhetoric calling for a "travel ban" – problematic language, given the rulings of 9th and 4th Circuit federal courts, which froze Trump's milder order.
It's true that those courts departed from precedent and legal reasoning in their adverse rulings, probing Trump's personal motivations behind the order rather than the text of the document. Trump is justifiably annoyed by this, as are Republicans in general, but the fact is, when the case is heard by the Supreme Court, at least four of the justices are going to do exactly the same thing.
By resurrecting the rhetoric of a travel ban, Trump is undermining his own lawyers, who have been arguing that the order is not a ban and that the president's intentions are completely reflected in the order itself, and not the leading edge of a potentially unconstitutional immigration enforcement scheme. George Conway, Kellyanne's husband, and certainly no enemy of the president, noted in his own Twitter account, "These tweets may make some ppl feel better, but they certainly won't help OSG [Office of Solicitor General] get 5 votes in SCOTUS, which is what actually matters[.]"
More to the point, in other tweets posted around the same time, Trump acted as if someone else were president: "The Justice Dept. should have stayed with the original Travel Ban, not the watered down, politically correct version submitted to the S.C." And "The Justice Dept. should ask for an expedited hearing of the watered down Travel Ban before the Supreme Court--& seek much tougher version!"
Trump issued the watered down, politically correct version of the immigration order he's now blasting. No doubt it was not his personal preference, and he did it upon being advised that it had a better chance surviving inevitable constitutional challenges. Now that the watered down order has been successfully challenged at least at the Circuit Court level, Trump appears to regret having given in to his advisors. Still, he did it.
All this suggests that Trump indeed is a kind of a regretful president, almost instinctively reassuming his status as an outsider, which leads to the easily mockedphenomenon of effectively attacking his own administration. For many core Trump supporters, this is perfectly okay; they elected him to shake things up, and he's certainly done that, though to what end, other than the tremors he creates, is unclear.
It's long been a fantasy of republicans, reaching back to Roman times, of having a reluctant outsider as leader with no real interest in actually taking the levers of power, doing nothing more than needs be done. The republican Roman ideal was Cincinnatus, the warrior-aristocrat who left his farm and assumed the title of dictator in order to resolve a crisis and, having resolved it, returned to his plow. In more modern times, there are similar fantasies of the outsider taking over, like in the film Dave or the current (and execrable) television series Designated Survivor.
The Romans eventually learned that the days of Cincinnatus had passed, the empire grown too large, the country too rich, the various factions to powerful, to allow a virtuous man like Cincinnatus to rule again. Perhaps Trump's presidency is proof that we have reached that pass in America, too – that the outsider, no matter how virtuous or honest, must become an insider to get things done, even if it is foul for him and his supporters.
Trump is going to struggle if he is unwilling to own his own decisions, unwilling to see himself as an integral part of the executive and legislative process, unwilling to soil his hands on the levers of power and acquire the stink of compromise. Trump's refusal to abandon his tweeting is part and parcel of the outsider status and populism upon which he was elected. Were all things equal, it would be good that citizens on his feed get the unfiltered thoughts of their president night and day. Unfortunately, all things are not equal. Trump's tweets continue to hurt his administration more than they help.
Trump probably isn't really regretful or reluctant about assuming the presidency, but when he acts as though he were, he weakens the office.