On a personal level, Bolton has none of the rapport with Trump that other, more trusted advisers have cultivated. There’s no chance, for example, of Bolton hitting the golf course or sharing a bawdy joke with the President.
Perhaps most importantly, Bolton’s ability to influence the President may have peaked on April 9, 2018 — the day he began his job at the White House. Over the previous several months, as Trump grew frustrated with his then-national security adviser, H.R. McMaster, he was receiving a steady barrage of advice from Bolton via Fox News. Bolton arguably had more direct influence over Trump as a talking head on his favorite cable news network than he did as a White House official down the hall from the Oval Office.
A Republican fixture for decades in Washington, Bolton’s reputation is as someone who prefers to speak his mind, not get in line. That certainly held true during his time in the Trump administration.
Bolton was at odds with Trump in other areas, including Syria, the Iraq war and Vladimir Putin. In the same Telegraph op-ed in 2017, Bolton warned Trump that the Russian leader would lie to the President about everything from election interference to the Middle East. “Negotiate with today’s Russia at your peril.”
No rapport with Trump
Bolton might have survived longer if the division with Trump was just over policy. But the career Republican bureaucrat had little in the way of a personal relationship with the President that could have bridged the gap.
Unlike Pompeo or South Carolina senator Lindsey Graham, Bolton is not prone to backslapping or telling off-color jokes to establish rapport with Trump. Bolton does not golf, a favorite pastime of the President’s and where people like Kentucky senator Rand Paul — Bolton’s ideological foe — can get Trump’s ear.
Perhaps most humiliatingly, Trump even occasionally referred to his national security adviser as “Mike Bolton.”
By contrast, Pompeo is particularly friendly with Trump, which has given the Secretary of State the upper hand in power struggles on the national security team.
On the inside looking out
After Trump’s election, Bolton shifted his commentary toward advice for the new president. He broke through most successfully over the issue of Iran, since he and Trump were both staunch opponents of the nuclear deal.
Bolton’s ability to influence the President’s decision to break the agreement not only illustrates Bolton’s masterful maneuvering from outside the White House, but also Trump’s penchant for being skeptical of those around him.
In 2017, as Trump faced a periodic decision about whether to recertify Iran’s compliance with the deal, his national security team worked to encourage the President to do so, at least until the administration could finalize its Iran policy. According to a law passed by Congress, the President was required to certify Iran’s compliance every 90 days. But Trump was reluctant to even give this perfunctory approval to a deal that he had consistently opposed as a candidate.
Bolton’s op-ed attempted to take advantage of what one former senior White House official described as the President’s reliance on advice from “outside the room.” The future Trump administration official blasted “JCPOA supporters” within the administration who were insisting that “rejecting the deal would harm the United States.” Bolton called that “nonsense.” It was also what most of Trump’s national security team had been arguing in favor of.
Trump abruptly decided to reverse his decision and instructed his administration to no longer recertify the deal. An hours-long scramble by his national security team eventually convinced Trump to reverse his reversal and proceed to recertify Iran’s compliance. But it would be the last time the President would do so before exiting the deal entirely.
What Bolton provided in that particular moment was an option Trump had felt was withheld from him by the insiders in the Oval Office. But Bolton lost that advantage once he became one of those insiders. Combined with the rigidity of his own views and his lack of a personal relationship with Trump, accepting the job as national security adviser was Bolton’s undoing as a voice in Trump’s ear.