Since his first job out of law school, John Sullivan has decorated his offices with two framed family heirlooms to fortify himself on difficult days.

One is a photograph of his father in his days as a submariner in World War II. The other is a Newsweek cover from early 1979 showing his uncle, the last U.S. ambassador to Iran, surrounded by bearded Iranian students armed with assault weapons.

“On my worst days, no one ever shoved a bayonet in my face, and no one tried to blow me out of the water,” Sullivan said in an interview after stepping down as deputy secretary of state last month to become the next U.S. ambassador to Russia.

Sullivan arrived in Russia last week at a time when relations between the two countries are at rock bottom. Embassy staffing is paper-thin after a series of diplomatic expulsions. The inscrutable relationship between President Trump and President Vladimir Putin sometimes appears counter to U.S. policy toward an adversary. Russian trolls already are suspected of trying to interfere in the 2020 vote as they did in the 2016 election, and it will be up to Sullivan to call out the Kremlin.

As deputy, Sullivan faced his share of ordeals, and many more may lie ahead as he represents the Trump administration in Russia.

A veteran official of two previous Republican administrations, Sullivan held the No. 2 job at the State Department during some of the most tumultuous years in its history. He struggled through budget cuts, vacancies in key positions, an ill-fated “redesign” and a midstream leadership change.

A personable man known as the friendly face on the seventh floor, where top officials work, Sullivan has propped up lagging morale amid White House put-downs of career diplomats disparaged as the entrenched “Deep State.”

Though he was involved in many major policy and management decisions, Sullivan is best known to the public as the State Department official who told Marie Yovanovitch, the former U.S. ambassador to Ukraine, that she had been yanked home prematurely not because she had done anything wrong but because the president simply “lost confidence” in her.

Now Sullivan is taking on one of the most important and difficult jobs in American diplomacy.

“He has no illusions about the challenges in the job. He also has no illusions about the complexities of being an ambassador in this administration,” said Anthony “Toby” Moffett, a former Democratic congressman who occupied the office next to Sullivan’s at the Washington law firm of Mayer Brown.

“He doesn’t have rosy aspirations for moving the needle in a massive way,” Moffett added of Sullivan’s task to improve the contentious relationship.

Sullivan is not an expert on Russia and does not speak the language, but that is not unprecedented.

“He’s got good judgment, that’s always the main thing with ambassadors,” said Anne Patterson, a former senior ambassador. “And he has good relations with the White House. He’s got what we call ‘reach-back.’ That’s super important.”

'Step into the breach'

Sullivan’s transition is not a typical career trajectory. In a building viewed as a bastion of elitism, he often recalls his roots as the grandson of Irish immigrants who settled in Boston. His voice carries traces of his Southie upbringing. He is an avid hockey fan who plans to root for the Dynamo Moscow team of Alexander Ovechkin.

Sullivan met his wife, Grace Rodriguez, when they were both attending Columbia Law School. They have three adult children. None of his family will move to Moscow with him.

Sullivan says he was inspired to government service by his uncle, William, a career diplomat who was the U.S. ambassador to Iran when the embassy was briefly overrun and seized by militants in early 1979. William Sullivan’s exchanges with the White House grew acrimonious, and he was recalled by President Jimmy Carter several months before a more infamous takeover that began later that year.

Despite his uncle’s example, Sullivan did not initially gravitate to diplomacy.

Between stints at private law firms, he worked in the Justice, Defense and Commerce departments during both Bush administrations. Under Trump, Sullivan initially was nominated to be general counsel for the Defense Department. But Trump’s first secretary of state, Rex Tillerson, asked Sullivan to serve as his deputy when the White House rejected his first choice. Sullivan was confirmed on a 94-to-6 vote.

The department was in turmoil. Veteran diplomats were leaving in droves, and many senior positions were vacant. Sullivan and Tom Shannon, then the undersecretary of state for political affairs, had a crushing workload but had to “step into the breach,” Sullivan said.

“That’s what I’m proud of — that I was able to handle all that in extremely stressful times. The world doesn’t take a breather because there aren’t five or six undersecretaries confirmed at the State Department.”

Shannon recalls it as a “really challenging period.”

“He had to build a relation with Secretary Tillerson, he had to build a relation with the White House and he had to build a relation with the building, all at the same time,” said Shannon, who signed a public letter backing Sullivan’s confirmation. “John was a steady hand, a fair hand, at a really complicated moment.”

Although he is a Republican and a political appointee, Sullivan’s approach is widely viewed as nonpartisan. Many are comforted by his family ties to the Foreign Service. Besides his late uncle, two cousins are diplomats.

He is known throughout the building for his commitment to diversity and workplace respect. He implemented mandatory training on sexual harassment and unconscious bias. He spoke to every class of incoming diplomats, and to interns and affinity groups. He attended every Pride event for LGBT employees.

'I serve at his pleasure'

Sullivan’s critics contend he should have spoken out more forcefully on behalf of diplomats who came under political pressure because they had worked on Obama-era initiatives that were unpopular in the Trump administration.

Others are puzzled that he was unable to keep Yovanovitch in Kyiv, particularly given his uncle’s recall under similar circumstances.

Three years into the Trump administration, the State Department remains a place where employees say they are afraid to mention Hillary Clinton’s name, and some new staffers are unaware that an exhibition space is officially called the Hillary Rodham Clinton Pavilion.

“There are some who would have wanted more public pushback on the Marie Yovanovitch stuff, the Bill Taylor stuff,” said a former diplomat, speaking on the condition of anonymity to be frank. Taylor served in Ukraine on a temporary basis after Yovanovitch was ousted.

“But I don’t think they understood how thin the ice was that he was crossing. How at risk he would have been, if he’d been more public in his assessments of what was going on,” the former diplomat said.

Sullivan said he is not haunted by the role he played in the Yovanovitch incident, calling it the president’s prerogative to pick an ambassador.

Now Sullivan is one.

“I’m honored that he’s picked me to be his representative in Moscow,” he said of Trump. “And if for some reason he should lose confidence in me, it’s the price of admission to be an ambassador. I serve at his pleasure, and if he is no longer pleased with my service, I will be brought home.”