It’s one of the enduring mysteries of Barack Obama’s presidency, as it sinks toward the sunset: How did this suave and intelligent guy, with the cosmopolitan demeanor, the sardonic sense of humor and the instinct for an irresistible photo-op, end up running the most hidden, most clandestine and most secrecy-obsessed administration in American history? And what does the fact that nobody in the 2016 campaign — not Bernie Sanders, not Hillary Clinton, not anybody — ever talks about this mean for the future? The answer to the second question is easy: Nothing good. The answer to the first one might be that those things are unrelated: Personality doesn’t tell us anything about policy, and our superficial judgments about political leaders are often meaningless.

Bill Moyers warned me about this some years ago, when I asked him how he evaluated George W. Bush as a person. He wasn’t much interested in character or personality in politics, he said. Lyndon Johnson had been one of the most difficult people he’d ever known, and Moyers had never liked him, but Johnson was an extraordinarily effective politician. I wasn’t sharp enough to ask the obvious follow-up question, which was whether Johnson’s personal flaws had fed into his disastrous policy errors in Vietnam.

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Bill Moyers has forgotten more about politics than I will ever know, but the thing is, I do perceive a relationship between surface and substance, and I believe we learn something important about people almost right away. George W. Bush was profoundly incurious about the world, and insulated by layers of smarter people and money. Richard Nixon was always a creep. Bill Clinton wanted to make you cry and get your panties off. Ronald Reagan never had any idea what day it was. Barack Obama seems like a smart, funny, cool guy, and maybe he’s too much of all those things for his own good. Maybe we will look back decades from now and perceive the Obama paradox — the baffling relationship between his appealing persona and his abysmal record on surveillance, government secrecy and national security — in a different light. For one thing, whatever they told him between November of 2008 and January of 2009 must have been really scary.

I called up John Kiriakou, a former CIA agent who spent 23 months in federal prison thinking this stuff over, to see if he could help. Kiriakou is one of the nine government leakers or whistleblowers that the Obama White House and/or the Justice Department has sought to prosecute under the Espionage Act, a law passed under Woodrow Wilson during World War I that was meant to target double agents working for foreign governments. (Among the other eight actual or prospective defendants are Chelsea Manning and Edward Snowden.) Under all previous presidents, incurious George included, the Espionage Act was used for that purpose exactly three times. If you’re keeping score, that’s nine attempted prosecutions in seven years, versus three in 91 years.

Kiriakou had a whole lot to say, especially about former Attorney General Eric Holder and current CIA director John Brennan, whom he sees as the prime movers behind the administration’s secrets-and-lies agenda — and also as the guys who railroaded him over what he describes as a minor indiscretion. Kiriakou spent 15 years in the CIA, first as an analyst and then as a covert operative. He was involved in the capture of Abu Zubaydah, and apparently knew that the alleged senior al-Qaida operative was waterboarded by CIA interrogators, although he was not directly involved.

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Kiriakou’s decision to talk about CIA torture in a 2007 interview ultimately landed him in prison. But it’s an arcane and suggestive tale and, at least officially, his crime had nothing to do with what he said about Zubaydah and waterboarding. Kiriakou revealed the last name of a covert agent — inadvertently and in passing, he says — to an ABC News journalist named Matthew Cole, who said he was planning to write a book but was actually gathering information for defense lawyers working with detainees at Guantánamo Bay. Later, Kiriakou believes, Cole became a government informant. The whole thing would puzzle John le Carré and Immanuel Kant put together.

Even though Kiriakou’s purported offense occurred when George W. Bush was in the White House, it was Obama’s Justice Department that decided to investigate and prosecute him, a three-year process that left him bankrupt, unemployed and more than a million dollars in debt. In the end, he would up spending nearly two years in prison because he mentioned one person’s last name in one email. When it comes to why the Obama administration has repeatedly taken that approach, Kiriakou sounds just about as puzzled as the rest of us.

I laid out my limited understanding of the Obama paradox, pretty much the way I did a few paragraphs ago, and Kiriakou sighed. “If this had not happened to me, I would be looking at the Obama presidency as one of the most successful and most progressive presidencies in my lifetime, on everything from gay rights to the economy,” he said. “His foreign policy has been largely successful, if you don't necessarily focus on the Middle East. But I just can't get past these whistleblower prosecutions, most especially my own.

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“People ask me all the time if I blame Obama for this, and I tell them I don't think Obama has any idea who I am,” he went on. Holder and Brennan had the president’s ear, Kiriakou believes, and for reasons of their own they were devoted to punishing all leakers who made the administration look bad. “I still have friends in the White House. I still have friends in the CIA. They tell me that it was John Brennan who was the real impetus behind these prosecutions, when he was assistant national security advisor for counterterrorism. Brennan was obsessed with leaks just like Holder was obsessed with leaks, and it was Brennan who pushed these prosecutions forward.”

What we see now, at the tail end of Obama’s presidency, is the FBI (which is under the authority of the Justice Department and hence the White House) trying to force Apple to hack open the world’s most popular and beloved handheld device, one of whose principal selling points is its unbreakable encryption. Although the president has taken no visible role in the iPhone struggle, it exemplifies what you might call the Obama line: I’m a reasonable guy and this is a special case. Don’t you trust me with your secrets?

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“People just don't seem to understand that this case has very broad civil liberties connotations,” Kiriakou says. “This is not a fight between Apple and the FBI. If Apple allows the FBI in this one time, what's gonna stop them from asking another time? Indeed, the FBI has now asked for access to nine different phones in nine different cases. All the other cases are drug cases. So that has started already. Then, if such a back door exists, repressive regimes are going to use it and hackers are going to use it and the next thing you know everybody's got access to your phone. I mean, haven't we given up enough of our civil liberties already? All these incremental losses of our civil liberties over the years, that people either don't sense or don't care about, are bad enough. Now we have to worry about the FBI going into our phones anytime they want."

Obama came into office promising to run the most transparent and open White House in history and has done precisely the opposite. His administration has kept entire areas of national security, intelligence and anti-terrorism policy under the cloak of executive privilege. That includes the drone war that has killed several thousand people in at least six different countries. Despite the best efforts of international watchdog groups, we will probably never know its full scale and scope, or how many civilians have died in drone strikes.

It also includes the infamous “kill list” of individuals whom the president has personally determined are subject to summary execution without trial. If one person has Obama’s ear on this question, it would seem to be John Brennan, who during his tenure at the CIA has transformed the agency into a clandestine military force with no uniforms, no systems of accountability and no obligation to respect the ordinary rules of war.

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At least two known individuals on the kill list have been United States citizens, including the influential al-Qaida imam Anwar al-Awlaki, who was born in New Mexico. (Awlaki’s teenage son, also an American citizen, was himself killed by a drone a few weeks after his father. His death is believed to have been collateral damage.) It was a year and a half after Awlaki’s death before the legal framework that supposedly authorized the president to kill him was discussed in public, and that only happened after a non-classified Justice Department memo was leaked to the press, perhaps with permission from above.

That all sounds like old news in the middle of an increasingly unhinged election year whose sole foreign policy issue is the national panic over ISIS, a group that, if we stretch the point, might plausibly be held responsible for the deaths of a few dozen Americans. But just because none of this is a campaign issue does not mean it has gone away. Drone pilots are beginning to speak out about the video-game deaths they inflict on strangers thousands of miles away. A group of Air Force veterans recently published a letter to Obama in the Guardian describing the drone war as a “fundamental recruitment tool” for groups like ISIS and a driving force of terrorism. The wife of another imprisoned CIA leaker, Jeffrey Sterling (who has consistently denied any wrongdoing), has mounted a campaign aimed at convincing Obama to pardon her husband before he leaves office, which is one reason I had John Kiriakou’s phone number.

On the other end of the spectrum, Donald Trump has captured a different segment of the national mood by suggesting that however many people Obama is killing in secret, it isn’t enough. Other Republican candidates are somewhat less eager to talk about the drone war or the previous president’s policies of “extraordinary rendition” and “enhanced interrogation.” Trump, to say the least, is not other Republicans. He has more or less promised to bring back the Bush torture policy on steroids, stripped of any prevarication or mixed emotions.

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It would be ludicrous to expect Hillary Clinton, a longtime national-security insider with close ties to the intelligence community, to adopt a different approach in the White House. Kiriakou says that an aide to Bernie Sanders wrote him a letter while he was in prison, telling him that the Vermont senator believed he had provided an important national service by revealing the CIA torture program. But issues of surveillance, spying and secrecy are never mentioned in Sanders’ fire-and-brimstone campaign speeches, which largely focus on the “free stuff.” That’s “extremely disappointing,” Kiriakou says, but suggests that Sanders’ team tested out that material and discovered that it didn’t resonate with voters.

So what’s the deal with Barack Obama? How did our coolest-ever president also turn out to be the one who pursued leakers and whistleblowers with a vengefulness and vigor without precedent in American history? To paraphrase what one of Stalin’s defeated rivals wrote in a letter to the dictator on the eve of his execution, why was John Kiriakou’s destruction useful or necessary to Obama? “I’m not sure that I can answer that question,” Kiriakou said, “and, believe me, I’ve thought about this a lot over the last four years.”

Then he pretty much did answer it, and the answer is depressing. “When you've got four shiny stars on your shoulder and you're described as the ‘president's favorite general’ and you say something that makes the president look good, you're not going to get an espionage charge.” He is talking there about retired Gen. James Cartwright, who is suspected of leaking info about Stuxnet, the CIA computer virus that targeted Iran’s nuclear program, but was never prosecuted. “Or when you have those four shiny stars on your shoulder and you leak to your freaking girlfriend the names of 10 covert operatives, you get a pass.” That would be Gen. David Petraeus, the former CIA head who revealed far more information than Kiriakou did, and served no jail time.

“Or when you're Hillary Clinton and you've got whatever it is now, 83 top-secret documents on your private server, you're gonna get a pass,” Kiriakou continued. “It's when you report on waste, fraud, abuse or illegality, or you embarrass the government or contradict a policy, that’s when the whole weight of the government is gonna crash down on your head.”