(Bloomberg) -- As President Donald Trump prepared to kill a top Iranian general on Thursday, vastly escalating his conflict with Tehran, he sought the advice of a relatively new aide who has rapidly become indispensable to the president: National Security Adviser Robert O’Brien.
O’Brien was celebrating the holidays in Pasadena, California, more than two thousand miles from Trump’s Mar-a-Lago resort in Florida. Other key aides including Secretary of State Michael Pompeo and Acting Chief of Staff Mick Mulvaney consulted with the president remotely, but a government jet was dispatched to fetch O’Brien and bring him to Palm Beach for the strike on Qassam Soleimani.
Killing Soleimani -- the influential leader of the Islamic Revolutionary Guard Corps’ Quds Force and a central figure in decades of Middle East unrest -- was one of the most consequential military decisions of Trump’s three-year presidency. His two most recent predecessors decided against it, out of concern the general’s death would prompt retaliation and risk plunging the region deeper into chaos.
It was telling, then, that Trump summoned not his chief of staff or one of his Cabinet secretaries, but an aide who has won him over in recent months with a calm loyalty and unfailing willingness to implement the president’s at times controversial and dramatic lurches in American foreign policy.
O’Brien may face scrutiny over the strike as lawmakers and the public seek more details about “imminent” attacks Trump said Soleimani was planning. And if Iran retaliates, as it has promised, questions about the decision will intensify.
By Trump’s Side
O’Brien, 53, was by the president’s side in the gilded rooms of Trump’s Florida resort, briefing him on Soleimani’s history and intelligence reports indicating he was planning attacks on Americans in Iraq and other locations. He was there when military commanders informed the president that the strike was successful.
He discussed the aftermath of the attack with Trump throughout the weekend and returned to Washington with the president aboard Air Force One on Sunday. He was in Trump’s cabin as reporters entered at Trump’s invitation, along with other aides including Mulvaney. In his remarks, Trump defended his threat to bomb Iranian cultural sites in the event of retaliation for Soleimani’s killing.
A corporate lawyer in California before he joined the administration, O’Brien is less likely to strenuously object during discussions with Trump than his predecessors John Bolton and H.R. McMaster.
Senator Mike Lee, a Utah Republican, spoke to O’Brien within hours after news broke on Soleimani’s death. He said in an interview that he has concerns about what happens next. But he’s confident O’Brien will push back “in circumstances where he felt the president was taking the wrong course of action, and offer a dire warning.”
“O’Brien’s not a guy who will walk out of a meeting holding a notepad that says 5,000 troops to Venezuela. He’s not itching for a new war,” Lee said, referring to an incident in Bolton’s tenure. “That’s not his style.”
Presidential Balm
Rather than trying to restrain Trump from riskier decisions, O’Brien has instead enabled big swings -- like the president’s decision in October to abruptly withdraw U.S. troops from Kurdish-held territory in Syria, the military raid that killed Islamic State leader Abu Bakr al-Baghdadi and the Soleimani killing. In meetings on all three situations, O’Brien offered pros and cons, but ultimately agreed with the courses of action and didn’t dissent, according to two people familiar with the discussions.
The new national security adviser is close to Pompeo, unlike Bolton. O’Brien is also friends with Bolton, though the two haven’t spoken since O’Brien assumed his current job, according to people familiar with the matter.
O’Brien’s counsel has proven to be a balm for Trump, who aides say has been cheered by their conversations on some of his gloomiest days. But some aides are concerned that the president may not be well served by O’Brien’s accommodating approach. Those concerns have been amplified as Trump has replaced other top advisers with loyalists seen as unlikely to challenge his thinking.
One of O’Brien and Trump’s shared priorities -- dramatically reducing the size of the National Security Council -- has bred concern that policy experts with deeper understanding of the possible consequences of the president’s actions might be sidelined. Richard Goldberg, the director for countering Iranian weapons of mass destruction at the NSC, is departing the White House on Monday.
Critics, including Senator Chris Murphy, a Connecticut Democrat, say the confrontation with Iran is evidence that Trump isn’t getting robust advice.
So far, the NSC has shed about 60 positions. Additional departures as aides rotate back to their home agencies are expected to leave the policy team with about 100 people – roughly the size of the staff under President George W. Bush’s national security adviser, Condoleezza Rice.
Trump’s critics say O’Brien is helping cement a transactional foreign policy in which quick U.S. “wins” are the priority, regardless of long-term strategy and positioning. O’Brien has difficulty keeping to his schedule and at times -- perhaps to keep the president mollified -- has asked seemingly misplaced questions at briefings, according to two people familiar with the matter.
O’Brien told aides on Monday that he wants to stack up more “wins,” and that his staff should look for ways to achieve decisive action for the U.S.
O’Brien’s allies say he’s learning on the job, and argue that the president deserves a top foreign policy adviser who shares his worldview and approach. They also argue that because O’Brien is seen as an honest broker of the president’s intentions, he can be more productive in focusing foreign policy.
Trump’s Confidence
Despite a background that suggested he’d likely support a more traditional Republican foreign policy -- having previously advised the Mitt Romney, Scott Walker and Ted Cruz presidential campaigns -- O’Brien has shown a willingness to implement the president’s unconventional approach.
And Trump’s faith in O’Brien has been evident in cases small and large.
Less than two months after Trump named him his latest national security adviser, O’Brien flew around the world to fill in for the president at an annual summit of Southeast Asian nations.
He held a series of meetings with government leaders, including the prime ministers of Australia and New Zealand and Nobel Peace Prize laureate Aung San Suu Kyi, the Burmese leader who’s recently suffered international criticism for her complicity in the ethnic cleansing of Muslim Rohingya from her country.
Dispatching O’Brien to represent the U.S. was regarded as a slight by some of the countries in attendance. But it also illustrated Trump’s confidence in his new national security adviser.
In a meeting with Chinese Premier Li Keqiang, O’Brien pressed him about two Canadians jailed in Beijing shortly after Huawei Technologies Co. executive Meng Wanzhou was taken into custody in Canada at the request of U.S. prosecutors. The two men remain in detention after more than a year.
Hostage Negotiator
Many in the West Wing said they perceived a connection between Trump and O’Brien even before he got the job.
Multiple officials pointed to a day in late May when the president was particularly irritated: Bolton’s hawkishness had created fresh headaches with both North Korea and Iran; Special Counsel Robert Mueller was dominating TV screens in the White House; and sirens were wailing outside when, in a macabre display not far from Trump’s Oval Office window, a man lit himself on fire on the Ellipse.
But when O’Brien -- then special envoy for hostage affairs -- entered the Oval Office, Trump’s mood seemed to brighten almost instantly.
Three months later, O’Brien replaced Bolton, in part due to his success at winning the release of several U.S. hostages. Those wins boosted Trump’s standing with evangelicals and conservatives skeptical of his foreign policy acumen. Trump also regarded O’Brien as a handsome, clean-cut Mormon in nice suits, looking the part of a savvy foreign-policy hand.
O’Brien’s increasing media appearances ar further evidence of his stature with Trump. After the Soleimani strike, he briefed U.S. reporters on the record -- breaking from the practice of many other White House officials who prefer anonymity to avoid getting sideways with the president.
Venezuela Challenge
O’Brien is also making his mark on another key priority for Trump: Venezuela.
Drawing on his experience as a hostage negotiator, O’Brien played a role in getting six American oil executives transferred from prison to house arrest in Venezuela in December. Known as the “Citgo Six,” the Citgo Petroleum Corp. executives had been jailed by Nicolas Maduro’s government on corruption charges since 2017.
With O’Brien’s blessing, an NSC aide went to Mexico to meet with Argentina’s new president, Alberto Fernández. Fernández then spoke to Maduro about the well-being of the hostages, resulting in their transfer.
Now O’Brien’s trying to rekindle Trump’s effort to force Maduro from office. It will likely prove as much a test for the national security adviser as Iran. On Sunday, Maduro’s loyalists and other opposition leaders ousted Juan Guaido, whom the Trump administration had backed as the country’s legitimate president, from his position as leader of the country’s National Assembly.
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