As the head of U.S. Southern Command, Kelly’s first and only four-star assignment, he was prepared to carry out a directive to shut down the prison complex. At the same time, the general made no secret of the fact that he believed the president’s goal was misguided. “They’re detainees, not prisoners,” Kelly told Military Times back in January, during one of multiple interviews and less formal on-the-record exchanges as his 45-year career came to a close. “The lifestyle they live in Guantanamo is — they can't simply be put in a prison in the United States.
"Every one," he added, "has real, no-kidding intelligence on them that brought them there. They were doing something negative, something bad, something violent, and they were taken from the battlefield. There are a lot of people that will dispute that, but I have dossiers on all of them, built and maintained by the intelligence community, both military and civilian.
"There are no innocent men down there."
Kelly, 66, is one of at least four candidates under serious consideration to become President-elect Donald Trump’s Homeland Security secretary, though Reince Priebus, whom Trump appointed as White House chief of staff, indicated on “Meet the Press” last week that Kelly also is being eyed to lead the State Department. Either role would afford him considerable influence as Trump begins to shape policies on national security, foreign policy and immigration, including his controversial calls to erect a 2,000-mile barrier along the U.S.-Mexico border and deport millions of people who’ve come to the United States illegally.
Kelly has declined to comment about his prospective role in the Trump administration.
He is one of several former senior military officers in whom Trump has taken an interest as he seeks to fulfill his campaign promise to “drain the swamp” of establishment insiders filling key posts within the executive branch. The general has a scholar’s appetite for reading and sharp viewpoints on America’s role abroad. He has extensive experience in the Middle East, having spent about two years leading combat forces against the Islamic State’s Sunni Arab forerunners in Iraq’s Anbar province. But perhaps most important to Trump, Kelly is an expert on Latin America — and he is decidedly not one of Obama’s guys.
The general found himself at odds — and eventually on the outs — with the Obama White House. He spoke out forcefully and publicly on a range of issues beyond Guantanamo. Having lost a son in combat, Marine 1st Lt. Robert Kelly was killed six years ago in Afghanistan, the general delivered several pointed, passionate speeches about the sacrifice being made by American families as the country’s war with violent extremists seemed only to be worsening. And he spoke to Congress in very stark terms about the perceived vulnerability of America’s borders.
The question now is whether Trump, as president, would tolerate a Cabinet secretary with an unapologetic record for, as the general puts it, telling "truth to power.” During the campaign Trump declared that he knows more than America’s generals and admirals do, but he also lamented that they’ve been “reduced to rubble” under Obama. So perhaps the more important questions are: How would Kelly’s experience come to bear on whichever agency he may be asked to run, how do his views dovetail with the president-elect’s and, ultimately, would Trump even heed this general’s best advice?
James Mattis, another retired Marine general whose tenure in uniform and on the battlefield often intersected with Kelly’s, is said to be Trump’s leading candidate to run the Defense Department. A source familiar with Trump’s discussions said Mattis told the president-elect that Kelly also would make a solid defense secretary. Kelly reportedly said the same about Mattis. The source spoke to Military Times on the condition of anonymity, citing the sensitivity surrounding internal deliberations.
Like Kelly, Mattis clashed with the Obama White House. He was most vocal about the president’s stance toward Iran, with which the administration negotiated a nuclear proliferation accord that’s been endlessly criticized among those on the political right. It’s believed by many observers that both generals’ military careers ended prematurely because they refused to publicly support Obama’s agenda while holding convictions to the contrary.
"When I first came to know General Kelly, he was just a war fighter. But as time wore on in this administration, Kelly transformed,” said Rep. Duncan Hunter, a Marine Corps veteran who served under Kelly during the Iraq war. Hunter, a California Republican and member of the House Armed Services Committee, said that he and Kelly remain close.
“It killed him to not be able to talk about what he saw happening,” the congressman said. “He gives honest, unadulterated advice. It was interesting to see the change from 'everything's fine, we're not going to say anything, we're going to go execute our duties,' to 'this is wrong and I've got to talk about it.' And in the end that's probably what did John Kelly in.”
THREATS ALONG THE SOUTHERN BORDER
Trump and Kelly met in New Jersey on Nov. 20. They discussed the general’s diplomatic background and a host of global security concerns. The meeting included Priebus, who also chairs the Republican National Committee, and Steve Bannon, the Breitbart News executive whom Trump made his chief strategist. The discussion largely focused on the general’s experience at Southern Command, one the military’s nine unified combatant commands. SOUTHCOM, as it’s known, gave Kelly purview not only of Guantanamo Bay but also the massive criminal network that has metastasized from the trafficking of drugs, weapons and people throughout South America, Central America and the Caribbean.
And if not Kelly, whoever heads up Homeland Security or State may be hard-pressed to match the general’s wealth of contacts in this part of the world, and his depth of understanding about the socioeconomic and geopolitical dynamics there. The source close to Kelly said the general has “better relationships in Latin American than the State Department does.”
That source highlighted the Alliance for Prosperity, which Kelly played a lead role brokering during late-2014 and early-2015. It resulted in an initial U.S. investment of nearly $1 billion for Honduras, Guatemala and El Salvador, which has experienced more murder per capita than any other nation in the last two decades, according to the World Bank. The initiative aims to spur economic development, promote education, and curtail criminal activity and human trafficking.
In Washington, it was an important win for the general. He felt the administration had largely ignored many of his assessments about threats facing the U.S. that emanate from Latin America. Just days after the White House announced its support for the alliance, in mid-March 2015, Kelly appeared on Capitol Hill to offer his annual overview of Southern Command’s budgetary needs. With his tenure about to expire, he used the opportunity — “my third and likely final year in command,” he told lawmakers — to highlight in stark terms what he considered the American government’s dangerous underestimation of the threat posed by what he branded “transnational organized crime.”
“Unless confronted by an immediate, visible, or uncomfortable crisis our nation's tendency is to take the security of the Western Hemisphere for granted,” the general wrote in prepared remarks for the Senate Armed Services Committee. “I believe this is a mistake.”
The smuggling routes used by drug cartels and other criminal elements active in Latin America are ripe targets for international terror groups — specifically the Islamic State, Kelly warned Congress, citing online message traffic calling for ISIS adherents to seek entry into the U.S. via its southern border. “Southern Command has accepted risk for so long in this region that we now face a near-total lack of awareness of threats and the readiness to respond, should those threats reach crisis levels.”
He’d issued a similar warning to Congress the year prior.
A WALL ALONE WON’T SOLVE THE PROBLEM
Beyond his call to build a wall, Trump has promised to impose an aggressive crackdown on illegal immigration. When asked about those plans earlier this year, Kelly told Military Times that while he supports enhanced border security, that alone won’t address the underlying reasons people flee Latin America en masse.
“I think you have to have — we have a right to protect our borders, whether they’re seaward, coastlines, or land borders,” Kelly said. “We have a right to do that. Every country has a right to do that. Obviously, some form of control whether it's a wall or a fence. But if the countries where these migrants come from have reasonable levels of violence and reasonable levels of economic opportunity, then the people won’t leave to come here.”
In his final statement to Congress as the head of Southern Command, Kelly addressed the role of human-rights education and training, calling it essential to U.S. objectives not only in Latin America but wherever America seeks to gain influence. Governments should be accountable to their citizens, he said.
While at Southern Command, Kelly also leveraged America’s military, diplomatic and intelligence assets to encourage impoverished or otherwise unstable nations in the region to provide better security and opportunity for their populaces. A big focus has been on teaching foreign militaries and law enforcement how to counter the powerful, wealthy drug cartels that perpetuate violence and drive people from their communities.
For that reason Kelly is fiercely opposed to illegal and recreational use of drugs, though he makes some exception where there is emerging evidence to suggest medical benefits may exist. Notably, marijuana has shown some promise in mitigating the anxiety some military personnel face as a result of post traumatic stress. Kelly is OK with that. But he opposes widespread legalization of pot, saying it undermines efforts to curtail the distribution of hardcore drugs like heroin, methamphetamine and cocaine.
“The solution there,” Kelly said, “is for Americans to stop using drugs. Now, you’re never going to go to zero, but we’ve got great programs to convince Americans not to do things — or to do things. We’ve got great anti-smoking programs. I think when I was a kid a pack of cigarettes was 25 or 30 cents, and 70 percent of Americans smoked. Now I think it’s 23 percent and, of course, it costs you a million dollars to buy cigarettes. Years ago, people didn’t wear seatbelts. Now most people wouldn’t get in a car without putting a seatbelt on.
“We know how to influence people. I just don’t think we have any kind of a drug-cessation program to speak of. Consequently, the drugs are imported and consumed. I think if Americans understood that doing a little blow on the weekend — on a college campus or here on Capitol Hill — isn’t harmless, if they understood what it’s doing to Honduras or El Salvador, or what it was doing to Colombia, I think they’d responsibly realize that this is not a good thing.”
‘TRUTH TO POWER’
Kelly is a Boston native who speaks with a thick, tough-guy New England accent. He’s a very close friend of Marine Corps Gen. Joseph Dunford, whom Obama made chairman of the Joint Chiefs of Staff in 2015. Kelly is well regarded throughout the military’s officer and enlisted ranks, where he spent two years in the early 1970s before leaving as a sergeant to attend college and earn a commission.
Coincidentally, his first military deployment was to Guantanamo Bay. He was a 20-year-old enlisted infantryman in 1971. And then, as now, all new personnel arriving on the island are given a briefing about the wildlife there, he recalled. Notably, everyone is told "don’t screw with the iguanas," the general said, grinning as he thought back to another Marine in his unit, a rough-hewn corporal from West Virginia who captured one of the the reptiles anyway — and then proceeded to butcher and cook it.
During his final trip to Cuba, in 2015, Kelly shared Thanksgiving dinner with the troops who manage Guantanamo's day-to-day operations, personnel under endless scrutiny from human-rights advocates and other watchdogs who oppose the facility's existence and remain skeptical of the detainees’ treatment there after revelations that many were subjected to vicious interrogation methods both at Guantanamo and at CIA-run “black sites” overseas. In his discussions with Military Times, Kelly touted those troops' professionalism, saying everyone held at the prison is well cared for and treated "humanely."
The source close to Kelly said he built “extraordinary relationships” with the human rights groups who monitor the prison, that this was such an intense focus of the general’s that he brought all of his subordinates at Southern Command to the Holocaust Memorial Museum in Washington. “And he told them ‘this is what happens when you abuse your power,’” the source said.
Today, 60 suspects remain at Guantanamo Bay, and Trump has indicated he may look to expand the facility. Hunter, the congressman, said that Kelly understands “the value of Guantanamo,” and that because of him, Congress successfully blocked Obama’s efforts to close it.
“We're in Iraq and Syria and Afghanistan. We're not bringing anybody home to Guantanamo, right? We don't have prisons anymore where we can interrogate people. What are we doing with the people that we're capturing now?" Hunter said "... These guys are making IEDs. They're killing Americans. They're killing our allies. Yet there's nothing we can do with them. Guantanamo was the perfect place for that. Kelly understands that Guantanamo is a necessary thing for the type of war that we're fighting right now. And he talked about it.”
By the time Kelly retired, his relationship with the administration had become so strained that in the weeks before the general signed off at Southern Command, multiple White House officials accused him and other military leaders of actively undermining efforts to close Guantanamo. Kelly disputed those claims while the White House, at least publicly, sought to distance itself from them. But those closest to him see the episode as evidence that the president neither valued nor benefited from such unvarnished advice.
Former Defense Secretary Robert Gates, for whom Kelly worked as a senior military adviser in 2011, told Military Times that the general’s candidness was an asset at the Pentagon. The pair worked together for about four months, from the first days after Kelly's son was killed, through the Navy SEAL raid on Osama bin Laden's compound in Pakistan and early implementation of several budgetary moves designed to rein in wartime spending.
In recalling the bin Laden operation, Gates said that Kelly, then a three-star general, played a subtle but key role arranging an important 11th-hour meeting between the secretary and Mike Vickers and Michèle Flournoy, then the department's top executives for intelligence and policy. That was “an otherwise very busy day,” said Gates, who'd had reservations about sending the SEALs into the compound in Pakistan where bin Laden was hiding.
He worried there would be grave consequences if the mission failed, and preferred instead to let an airstrike do the job. Vickers and Flournoy made “one last effort to persuade me to support the raid, and they were successful," he said. "I called the national security adviser [Tom Donilon] and told him to tell the president that I was completely on board. John [Kelly] played a key role in making sure those folks got into my office at that time to make their case."
Kelly, Gates recalled, always tried to be constructive, never hesitating to offer his opinion if he felt people were not leaning forward. "Or, in the event of a military operation or initiative, if he thought the constraints were too great or that it was ill conceived," he said. "He wasn't afraid to speak his mind to civilian superiors. Always respectfully. And always prepared to move on whatever the decision."
Obama chose Kelly for the Southern Command job in 2012. It was a prestigious assignment, and a good fit. As a one- and two-star combat commander in Iraq, Kelly was integral to what became known as the Anbar Awakening. The movement succeeded, for a time, in curtailing the sectarian bloodshed that had gripped the country since Saddam Hussein's fall in 2003, bringing with it the tenuous prospect of stability as Sunni militias fought alongside forces fielded by the Shiite-led government to flush al-Qaida from key cities such as Ramadi and Fallujah.
In many ways, it was the success of Kelly and others in managing that fragile alliance which enabled Obama to make good on his campaign pledge to end the U.S. occupation of Iraq.
As a three-star general, Kelly led the Marine Corps Reserve while simultaneously overseeing the service's element within U.S. Northern Command, which coordinates with other federal agencies to monitor potential threats against the homeland. NORTHCOM also tracks criminal activity in Mexico, whose military, with U.S. advisement, continues to fight the powerful drug cartels responsible for fueling violence throughout the region. He also served as the senior military adviser to Gates' successor as defense secretary, Leon Panetta. And with multiple prior assignments that brought him through Washington, dating back to the 1980s, Kelly had developed a keen understanding of Congress and the dynamics (and theatrics) that define political life inside the Beltway, a skill that complemented his demonstrated strategic abilities.
Once at SOUTHCOM, it wasn't long before Kelly took aim at the national security issues central to that part of the world. His tenure there coincided with steep federal spending cuts that threatened to hinder his command's focus on drug interdiction and specialized military training for indigenous security forces battling the drug trade in places such as Honduras, El Salvador and Guatemala. The immigration crisis that peaked in 2014, when tens of thousands of women and children streamed to the U.S.-Mexico border, was the direct result of the surge in drug-related violence gripping Central America, Kelly told Congress at the time. And Americans' demand for those drugs was to blame, he said.
Moreover, the general had warned, the network those individuals leveraged to pay their way north presented a legitimate national security threat. He was asked about this during his annual testimony before the Senate Armed Services Committee, and Kelly gave a straightforward response. It made headlines. And the administration wasn't happy about it.
"We had defined the fact that hundreds of tons of cocaine make it across the southwest border," Kelly said in recalling the hearing. "And then another line of questioning. All of the heroin consumed in the United States makes it across the southwest border. The methamphetamine produced in Mexico makes its way across the southwest border. There were 70,000 unaccompanied children who’d come across the border in the previous several months. You get the point. And Senator Lindsey Graham said to me, once we’d established all of the facts, ‘would you say that the southwest border is secure?’ You know, what are you going to say? I said no, I don’t believe it is secure. And anything that wants to get in can get it. They just have to pay the fare. Well, that didn’t go over well."
But Kelly proved to be on point. He told the armed services committee that a small but growing number of radicalized Muslims from countries in the the Caribbean and South America had gone to wage jihad in the Middle East alongside the Islamic State group. And when they return, the general warned, there's little that would stop them from coming north to kill Americans.
"Boy," Kelly said, "Washington didn’t like that one either. But it's funny, a year later, everyone acknowledges that there is an ISIS, radical Muslim threat in the Caribbean."
It's a sensitive issue with Obama. Republican lawmakers and presidential hopefuls have assailed the president for initially downplaying the threat posed by ISIS while being slow to articulate how he intends to stop the spread of the group's ideology. Indeed, it was only after last November's terror attack in Paris that the administration began to ramp up the military component of its counter-ISIS strategy, which coincided with a robust marketing campaign aimed at reassuring the American public that federal, state and local authorities were working nonstop to prevent a Paris-style attack inside the United States.
Heading into the 2015 Thanksgiving weekend, as Kelly flew to Guantanamo Bay one final time, Obama, flanked by members of his national security team, gave a six-minute televised address to the nation. He highlighted the 8,000-plus airstrikes that U.S. warplanes had conducted to that point on ISIS positions inside Iraq and Syria, alluding to concurrent efforts targeting the group's finances and recruiting efforts, and plans to intensify the air campaign.
"Right now," the president said, "we know of no specific and credible intelligence indicating a plot on the homeland." Exactly one week later, Syed Farook and Tashfeen Malik killed 14 people in San Bernardino, California. The married couple had sworn allegiance to the Islamic State, but authorities concluded they had acted as lone wolves, saying there was no intelligence that would've tipped them to the attack. It rattled a nation already on edge, and eroded many Americans' confidence in what their leaders were telling them.
Today, although ISIS has been significantly degraded in Iraq and Syria, the group remains a serious threat as its ethos spreads to other parts of the world.
Kelly acknowledged that his final years in uniform were the most difficult to navigate. As he sees it, providing honest advice to those who run the government is a fundamental responsibility of someone in his position. While rising through the ranks, "the one thing I was always told is you absolutely have to tell truth to power," the general said. "Whether you’re a second lieutenant working with a captain and a lieutenant colonel, or a four-star general working with the Office Secretary of Defense and the White House, the decision makers have got to have ground truth. Otherwise, the decisions they make could be flawed — and that can be dangerous.
"I've learned that, in many cases, people say ‘I want ground truth’ and they don’t really mean it. There are warts all over this organization, as there are in many organizations, but you just have to tell truth to power and let the chips fall where they may. I know a lot of people may read that, if you put it in your story, and say 'easy for him; he’s a four-star.' But I would say some of the most challenging periods in my life, as a Marine officer, have been fairly recently, where you get into that civilian-military thing and the truth is not always welcome. It can cause some heartburn when you get a call from certain people in Washington who say 'it’s probably not a good idea to go down that road anymore.' But I say 'hey, that’s the truth. I'm at a congressional hearing, and they asked me a question. What am I going to do, lie?'"
Andrew deGrandpre is Military Times' chief editor. On Twitter: @adegrandpre.