Kelly embraced the legless and disabled Colombian troops one by one. "It was an emotional moment," Pinzón said. "He immediately identified with my soldiers. And after that we became very close friends."
From that day until Kelly's retirement from military service in 2016, he spent more than three years working in Latin America as head of U.S. Southern Command (Southcom). The period was a bridge in Kelly's late-career transformation from four-star general to field marshal of the Trump White House, where as chief of staff he spends long hours battling the agents of executive disorder.
Many in Washington were surprised to see Kelly emerge as an outspoken, combative member of President Trump's team. He had been widely depicted as less ideological than others in the president's orbit and as someone stirred to White House service by patriotic duty, not politics.
Those who worked alongside him in Latin America knew his worldview aligned more closely with Trump's than many may have realized.
As Southcom's commander, Kelly oversaw the Guantanamo naval base and its notorious prison, and not always in the way the Obama administration wanted him to. He took on illegal immigration, drug cartels and the political and military complexities of a peace deal in close ally Colombia that ended a 52-year war with Marxist rebels.
The job, said Pinzón, "turned him from a warrior into a statesman."
In a role that put him at the intersection of U.S. diplomacy, national security and Washington politics, Kelly also revealed conservative views and a reputation for troublemaking — qualities that would make him a prime recruit for Trump as he assembled his Cabinet.
Friends and former colleagues also said the Southcom job was restorative, helping Kelly come to terms with his son's death by channeling his energy and attention into civilian challenges outside his military comfort zone.
Kelly inspired intense loyalty and admiration among many of the Latin American and U.S. diplomats with whom he worked, but he clashed with senior State Department officials who viewed him as a narrow thinker prone to impolitic statements.
Trump named Kelly to his Cabinet in July 2017 on the recommendation of Defense Secretary Jim Mattis, also a former Marine general. When Kelly first joined the administration as secretary of homeland security, some immigrant advocacy groups assumed he would be a sympathetic figure, in part because of his familiarity with the forces driving Latin Americans to flee. But Kelly's years at Southcom had the opposite effect, hardening his views on border security.
This account of Kelly's time at Southcom is based on interviews with 14 current and former State Department, Homeland Security and military officials who worked closely with him. Most spoke on the condition of anonymity to offer their most candid views. When asked to comment for this story, Kelly declined.
Five months after taking charge of the White House as chief of staff, Kelly is pivotal to Trump's political fate, acting as his gatekeeper and perhaps most trusted adviser. He has tried to help his boss make better decisions by rigorously policing the quality of information — and the number of visitors — Trump receives.
Kelly has also pushed out some of the administration's most disruptive personalities, including former strategist Stephen K. Bannon, whose relationship to the president curdled last week with the release of Michael Wolff's insider account, "Fire and Fury," of a chaotic White House before Kelly's arrival.
In recent months, Kelly has receded somewhat from public view. In October, he gave a combative defense of Trump's handling of a phone call to the widow of a U.S. soldier who was killed in Africa, speaking publicly of his own son's death in a way few had ever heard. Kelly attacked Trump critic Rep. Frederica S. Wilson (D-Fla.), made false accusations against her, then refused to apologize.
Kelly drew more blowback days later when he stuck up for Confederate Gen. Robert E. Lee and blamed the Civil War on "the lack of an ability to compromise."
Kelly's former colleagues at Southcom viewed him as a flawed but magnetic leader, capable of establishing close, almost familial bonds with subordinates and the handful of peers who called him "Kel," not "General." They saw a bereaved father beneath the hard-shell, action-hero exterior and said his concern for those he leads — whether as a general or as a civilian — is completely authentic.
Others came to view him more harshly. "At first I thought he was a kind, almost grandfatherly figure, but then I came to see him as someone with impulse-control problems" who is "driven by ideology," said a former senior U.S. military official who soured on Kelly after working with him for several years.
Friends and former colleagues said Kelly was rarely guarded about his own political convictions. He viewed the Southcom job as a last stop before retirement and appeared to care little that his opinions might jeopardize future promotions.
Long before Trump campaigned on the renewal of American greatness, Kelly too spoke of the United States as a diminished nation, weakened by self-doubts, moral ambiguities and political correctness.
"I think he longed for a return to his version of the way things used to be, when things were simpler and less complicated, before there were women and gays in the military," the former military official said.
Kelly's sense of American decline deepened after his son was killed in Afghanistan, former colleagues said. Although he didn't openly blame President Barack Obama, they say, Kelly saw his son's death as a symptom of Obama's decision to telegraph his plans to wind down the war against the Taliban.
Kelly grew up in an Irish Catholic family in the Boston neighborhood of Brighton and was steeped in the war stories of World War II and Korean veterans. He enlisted in the Marines in 1970, though he did not deploy to Vietnam, and went on to a distinguished 45-year career that included combat in Iraq.
As Southcom commander, Kelly didn't easily adjust to working alongside U.S. diplomats, especially women. "This is a guy who spent 45 years in the company of men," said a senior U.S. official who has known Kelly for several decades.
To the frustration of senior State Department officials, Kelly would stray "out of his lane" by opening direct lines of communication with the presidents of Colombia, Honduras and other nations.
When U.S. diplomats and White House advisers organized a meeting with Honduran military and political leaders in 2015 to urge them to fight organized crime with police, not soldiers, "Kelly jumped in and started justifying what the Hondurans were doing," said a former Obama national security official who attended the meeting.
"We couldn't believe it," the official said. "We're supposed to have one position as the U.S. government, and Kelly basically breaks ranks and contradicts our policy right in the middle of the meeting."
Of all the top assignments that can go to a senior U.S. military officer, running Southcom is considered among the lower-profile posts, one that's focused on a region with no great strategic rivals like Russia or China, nor the hot-shooting conflicts of the Middle East.
Few viewed Kelly as one of the Pentagon's top strategic, geopolitical thinkers in the cut of David Petraeus, who led the wars in Afghanistan and Iraq.
"He's a smart, thoughtful guy, but more of a warrior than a global strategist," said a former senior U.S. official who worked with Kelly during his tenure at Southcom. "He's a yes-sir, no-sir, take-the-hill kind of guy."
Current and former State Department officials said Kelly was hard-wired to view Latin America's complex problems in stark good-vs.-evil terms. But his views evolved with time, and he impressed many would-be critics by regularly meeting with human rights organizations in the countries he visited.
In Guatemala, Kelly once toured a dilapidated forensic laboratory where volunteers had collected the remains of villagers massacred by soldiers during the country's civil war.
It wasn't the kind of thing Guatemalan military officials wanted Kelly to see, but he went anyway, said Rebecca Bill Chavez, who worked closely with him as the Defense Department's top civilian official for relations in Latin America.
Kelly later insisted Chavez visit the laboratory, because he was so haunted by seeing the remains of a young girl whose fractured skull was found with a hair tie. "He wasn't a Latin Americanist, but I think he truly wanted to know what happened and understand the history," Chavez said.
Kevin Whitaker, the U.S. ambassador to Colombia, developed a close relationship with Kelly and said the general consistently came to him "with an open mind."
"I don't know how many times I called him up when I needed something, and every single time he picked up, the answer was: 'Yes. What do you need?' " Whitaker said. "I had a partner I could absolutely rely on."
Latin American governments are acutely sensitive to the legacy of U.S. military intervention in the region and have a deep aversion to the presence of U.S. forces, so all but a few nations tend to keep American commanders at a distance.
Colombia, Washington's closest ally in Latin America, is the exception. The country has received more than $10 billion in U.S. security aid over the past 15 years. When Kelly arrived at Southcom, the government was negotiating a peace deal with leftist rebels, but the conflict was still going on. It was the one active war theater on Kelly's patch.
"He loved getting out into the field with the troops," said Luis Carlos Villegas, who became Colombia's defense minister after Pinzón was named ambassador to the United States.
Villegas said Kelly relished taking trips to jungle outposts, traveling in helicopters and on riverboats to meet Colombian soldiers and hear their combat stories.
Villegas was among the senior Colombian officials who were stunned in September when, six weeks after Kelly became Trump's chief of staff, the White House said it "seriously considered" labeling its closest Latin America ally a nation that has "failed" to meet international counternarcotics obligations.
The threat sank relations with Colombia to their lowest point in years. Officials in Bogota who had praised Trump for picking Kelly couldn't believe their friend would allow Colombia to be publicly humiliated in that way.
According to a former U.S. official with direct knowledge of the episode, it was Kelly who talked Trump out of criticizing Colombia in even more blunt terms.
A few weeks earlier, Trump had berated Colombian President Juan Manuel Santos, the winner of last year's Nobel Peace Prize, during an awkward phone call.
"Santos had called President Trump to express sympathy for the victims of Hurricane Harvey," the former official said. "The president gets on the line, Santos expresses concern, and then Trump eviscerates him over drugs for 24 minutes of the 25 minutes they were on the phone, telling him, 'We've got a disaster on our hands, and you care more about the [guerrillas] than the American people.' "
Relations with Colombia were heading sideways after that, but it was Kelly who "stopped the lunacy," the official said.
A hard-liner on borders
Kelly's years in Latin America left him with a view of U.S. border threats similar to Trump's, and not only illegal immigration and drugs. Kelly repeatedly told lawmakers that terrorist organizations could be plotting to sneak into the United States with the help of Mexican criminal groups, drawing eye rolls from Obama officials who saw him as parroting the alarmist headlines of far-right media.
"His statements were based on intelligence that simply did not exist in operational and intelligence channels," said a former senior military official who worked with Kelly at the time. "We'd look at each other and say, 'Where is he getting that?' "
At a White House news conference in October, Kelly said "women were sacred" when he was growing up, and former colleagues said the statement was a key insight into his views on border security.
Kelly reacted viscerally to stories of young women being abused and raped during the journey from Central America. "I would do almost anything to deter the people from Central America getting on this very, very dangerous network that brings them up from Mexico," Kelly told CNN this year when, as DHS secretary, he said he was considering a proposal to separate children from their parents after family groups cross the border.
Former colleagues at Southcom said they were surprised to see Kelly leap into the swirling center of Washington, six months after calling American politics a "cesspool" and admonishing former military leaders who waded into the muck. A few who remain loyal to him said they fear the White House is changing Kelly for the worse.
One former military official who has known Kelly for years described feeling "physically sick" watching him speak publicly about his son's death when Kelly was defending Trump after criticism that the president had botched a sympathy call to the widow of Sgt. La David T. Johnson, who was killed in Niger.
Kelly had made such calls myriad times, another longtime friend said, and Trump was likely following Kelly's advice when he uttered the line that stung the soldier's widow, telling her that her husband "must have known what he signed up for."
"I think John was trying to help him," the friend said. "So he pre-briefs the president, who has a famously short attention span, and when he gets on the line with the widow, he uses that line, and it backfires. So Kelly has to go out and protect the president, using his 45 years of service and the tremendous pain he carries as a father.
"It killed me; I felt so bad for him," the friend said. "Here he is defending somebody who got five deferments out of Vietnam, and that's got to eat at him."
The friend dismissed speculation that the 67-year-old Kelly — who works 16-hour days — would soon quit.
He's still a Marine, the friend said, and when a job gets hard, "Marines don't just walk away."