Four of the most well-known targets of President Barack Obama’s war on leaks — including Edward Snowden and Chelsea Manning — are among those who have requested pardons or commutations in the waning days of his presidency.

Lawyers who track Obama’s approach to clemency applications say all four — which also include retired Marine Corps Gen. James “Hoss” Cartwright and former CIA officer John Kiriakou — face long odds in part because of intense attention to the dangers of hacking and the national security leaks that follow.


The fact that the requests don’t meet the usual Justice Department criteria and aren’t covered by the special initiative Obama set up to reduce the sentences of non-violent drug offenders sentenced to long terms in federal prison also make them more unlikely.

“I think he’s going to announce a lot of names in the next few weeks. I don’t think any of them will be these big-name figures,” said Mark Osler, a law professor at the University of St. Thomas in Minneapolis. “This administration does have an aversion to high-profile cases generally.”

Obama also appears to be intent on avoiding the political firestorm that arose in 2001, after departing President Bill Clinton pardoned fugitive financier Marc Rich.

A White House spokeswoman declined to comment on Obama’s plans regarding his clemency power during his final days in office. Clemency applicants can go directly to the president without filing applications at the Justice Department, but Obama has suggested he’s intent on observing the typical process without the chaos that surrounded last-minute grants under Clinton 16 years ago.

Outside legal experts say the best-positioned of the leakers may be Manning, who received a 35-year prison sentence from a military judge after being convicted at a court martial of disclosing hundreds of thousands of classified and unclassified diplomatic cables and military reports to WikiLeaks.

The 35-year term stunned many observers because it was by far the longest sentence ever imposed in a leak case. There was also testimony that Manning, a transgender woman who was once deployed to Iraq, was experiencing a mental breakdown around the time of the leaks, sometimes collapsing in a fetal position on the floor of a military command center in Iraq. Her doctors say she has continued to suffer from gender dysphoria, which has proven difficult to treat in military prison. In September, facing a lawsuit, the Army agreed to provide surgery to allow Manning to complete the transition from male to female.

About 116,000 people have signed a petition on the White House website asking Obama to commute Manning’s sentence to the roughly six years she has already served. However, she remains outside traditional pardon or commutation guidelines because her appeal is still pending in an Army court.

Chelsea Manning. a transgender woman who was once deployed to Iraq, received a 35-year prison sentence from a military judge after being convicted at a court martial of disclosing hundreds of thousands of classified and unclassified diplomatic cables and military reports to WikiLeaks. | Getty

The clemency request presenting the most delicate timing for Obama comes from Cartwright, who pleaded guilty in October to lying to investigators probing leaks about top secret U.S. efforts to disrupt Iran's nuclear program. The retired four-star Marine general and former vice chairman of the Joint Chiefs of Staff is set to be sentenced by a federal judge Jan. 17, three days before Obama leaves office and President-elect Donald Trump is sworn in.

Cartwright faces a maximum of up to five years on the false statements charge and a fine of up to $250,000. Sentencing guidelines appear to call for a much shorter sentence, in the range of zero to six months, but federal prosecutors may ask for more time.

A Justice Department spokeswoman confirmed Cartwright’s pardon application, which could be supplemented with a commutation request after the sentence is imposed later this month. One of Cartwright’s attorneys, former Obama White House Counsel Greg Craig, declined to comment.

As Obama’s presidency has drawn to a close, human rights and privacy activists have also stepped up calls for Obama to pardon Snowden, the computer specialist who triggered an intense global debate on surveillance practices after disclosing the NSA’s program collecting details on billions of phone calls made and received by Americans.

The disclosure led to legislation Congress passed and Obama signed last year ending so-called bulk collection of the phone data by the government, but providing a streamlined process to collect portions of it from phone companies on a case-by-case basis.

Snowden, who took refuge in Russia after his high-profile leaks of NSA data in 2013, is wanted on three federal felony charges stemming from the disclosures. Administration officials have signaled that a pardon for Snowden is highly unlikely, in part because he turned over top secret information to journalists that went far beyond the controversial NSA domestic call-snooping program and included far more traditional intelligence-gathering overseas, including in war zones. His flight to Hong Kong and then Moscow has also undercut and complicated calls for a pardon, officials said.

The White House has urged Snowden to return from Russia and stand trial, but he and his lawyers have noted that he could face decades in prison and would likely not be allowed to argue to a jury that his disclosures were in the public interest or expose illegality.

“I can't pardon somebody who hasn't gone before a court and presented themselves, so that's not something that I would comment on at this point,” Obama said last month in an interview with the German magazine Der Spiegel. “I think that Mr. Snowden raised some legitimate concerns. How he did it was something that did not follow the procedures and practices of our intelligence community. If everybody took the approach that I make my own decisions about these issues, then it would be very hard to have an organized government or any kind of national security system.”

Experts agree that Obama’s pardon power is virtually unlimited, so his statement that he “can’t” pardon Snowden appears to have reflected his conclusion that it would be unwise to do so.

Obama does have some more exotic options open to him to try to encourage Snowden to come back, including the possibility of an advance commutation that would effectively cap the punishment the former NSA contractor could receive for allegedly stealing and disclosing national security secrets.

Legal experts said it’s hard to see Obama offering Snowden a commutation, without a carefully negotiated set of conditions that would likely involve Snowden acknowledging error on his part and pleading guilty to some offense. Without such a deal, even with a commutation, Snowden could still force the government into the spectacle of a trial and likely force more disclosures about sensitive surveillance programs.

“If Obama was of any mind to do this, he’d want meaningful conditions to be imposed on the commutation before trial that would make it acceptable to the public,” said Harold Krent, dean of the Chicago-Kent College of Law.

Rounding out the leak-related clemency requests is a pardon application from Kiriakou, who pled guilty in 2012 to disclosing classified information about a fellow CIA officer that connected him to the spy agency’s interrogation program for terrorism suspects. Kiriakou received a two-and-a-half year prison sentence which he completed in 2015.

Kiriakou and his supporters have long argued that it is bizarre that he was punished for disclosing the CIA’s use of techniques, like waterboarding, that many regard as torture, but those who designed, authorized and carried out the program never faced any charges.

There is some historical precedent for presidents granting clemency in leak-related cases.

In 2007, President George W. Bush granted a commutation to Vice President Dick Cheney’s former chief of staff, Lewis Libby, who had been convicted of lying and obstruction of justice in an investigation into the disclosure of the identity of CIA officer Valerie Plame Wilson. Bush wiped out Libby’s two-and-a-half- year prison sentence, but left intact Libby’s conviction and a $250,000 fine.

In Bush’s final months in office, Cheney pushed Bush to grant Libby a full pardon, but the president refused—reportedly further straining his relationship with Cheney.

And in 2001, Clinton issued a pardon to Samuel Morison, a former Navy intelligence analyst who was convicted in 1985 under the Espionage Act of sending classified spy satellite photos to Jane’s Defense Weekly.

Since Morison had long completed his prison sentence—originally set at two years, but cut to eight months under parole rules at the time—the pardon more than a decade later cleared Morison’s record, while also raising questions about the use of the tough, espionage-related law to pursue leak cases.

Such cases were rare before the Obama administration, with only three filed in nearly a century. However, at least eight were brought during Obama’s time in office, leading to criticism from First Amendment and whistleblower advocates.

Obama administration officials have said there was no deliberate effort to step up such prosecutions. They also noted that several of the cases came under investigation before Obama took office.

However, there were apparently some second thoughts about controversial tactics used to investigate the leaks. That reassessment led to policy changes in 2013 from Obama and former Attorney General Eric Holder. Justice Department guidelines were revised to make it more difficult to obtain search warrants for journalists’ emails and to force reporters’ testimony in court cases. Justice officials also pledged to notify news organizations in advance when seeking to obtain their telephone records.

“I am troubled by the possibility that leak investigations may chill the investigative journalism that holds government accountable,” Obama said then. “Journalists should not be at legal risk for doing their jobs. Our focus must be on those who break the law.”