So how was it decided Reality Winner should get 63 months for leaking classified information? Does it seem about right?

The questions in the title of this post are prompted by this news out of the federal criminal justice system via the New York Times: "Reality L. Winner, a former Air Force linguist who was the first person prosecuted by the Trump administration on charges of leaking classified information, pleaded guilty on Tuesday as part of an agreement with prosecutors that calls for a sentence of 63 months in prison." Here is more of the particulars and some context:

Ms. Winner, who entered her plea in Federal District Court in Augusta, Ga., was arrested last June and accused of sharing a classified report about Russian interference in the 2016 election with the news media. Ms. Winner, who is now 26, has been jailed since her arrest and wore an orange prison jumpsuit and white sneakers to the hearing. Her decision to plead guilty to one felony count allows the government both to avoid a complex trial that had been scheduled for October and to notch a victory in the Trump administration’s aggressive pursuit of leakers.

“All of my actions I did willfully, meaning I did so of my own free will,” Ms. Winner told Chief Judge J. Randal Hall on Tuesday. Throughout the hearing, Ms. Winner kept her hands behind her back while she answered questions about whether she understood the terms of the plea deal.

Ms. Winner, who was honorably discharged from the Air Force in 2016, was working as a contractor for the National Security Agency when she obtained a copy of a report that described hacks by a Russian intelligence service against local election officials and a company that sold software related to voter registration. The Intercept, an online news outlet that a prosecutor said Ms. Winner admired, published a copy of the top secret report shortly before Ms. Winner’s arrest was made public. The report described two cyberattacks by Russia’s military intelligence unit, the G.R.U. — one in August against a company that sells voter registration-related software and another, a few days before the election, against 122 local election officials.

At a detention hearing last year, the prosecutor, Jennifer G. Solari, said that Ms. Winner had been “mad about some things she had seen in the media, and she wanted to set the facts right.”...

Once rare, leak cases have become much more common in the 21st century, in part because of such electronic trails. Depending on how they are counted, the Obama administration brought nine or 10 leak-related prosecutions — about twice as many as were brought under all previous presidencies combined.

The Justice Department prosecuted Ms. Winner under the Espionage Act, a World War I-era law that criminalizes the unauthorized disclosure of national-security secrets that could be used to harm the United States or aid a foreign adversary. Ms. Winner’s prosecution galvanized transparency advocates, who mounted a publicity campaign in her support that even included a billboard in Augusta, the east Georgia city where Ms. Winner lived at the time of her arrest. They were particularly infuriated by a judge’s ruling that she be held until her trial....

Ms. Winner is the second person known to have reached a plea agreement with the Trump administration to resolve a leak prosecution. A former F.B.I. agent, Terry J. Albury, pleaded guilty in April, but prosecutors in that case have signaled that they will ask that he serve 46 to 57 months in prison.

The Justice Department has brought at least two other leak-related cases under the Trump administration.  Earlier this month, James Wolfe, a former Senate Intelligence Committee staffer, was arrested and charged with lying to the F.B.I. about his contacts with reporters, including a Times reporter with whom he had a personal relationship and whose phone records the department secretly seized, during a leak investigation; Mr. Wolfe has not been charged with leaking classified information, however.  He has pleaded not guilty.  Also this month, Joshua A. Schulte, a former C.I.A. software engineer, with charged with violating the Espionage Act and other laws based on accusations that he sent a stolen archive of documents and electronic tools related to the agency’s hacking operations to WikiLkeas, which dubbed them the Vault 7 leak. Mr. Schulte had already been facing child pornography charges.

A judge must still decide whether to approve her sentence after reviewing a report that prosecutors will present.  But prosecutors’ recommendation of more than five years in prison — followed by three years of supervised release — was unusually harsh for a leak case.  For most of American history, people accused of leaking to the news media were not prosecuted at all.  In the flurry of cases that have arisen during the 21st century, most convicted defendants were sentenced to one to three-and-a-half years.

One — Chelsea Manning, who was convicted at a military court-martial for sending large archives of military and diplomatic documents to WikiLeaks — was sentenced to 35 years in prison, but served only about seven years because President Barack Obama commuted the remainder of her sentence.

As this article suggests, there is not a lot of history of sentences for these kinds of leaks, and arguably the Chelsea Manning case sets a notable benchmark for how high a sentence might go for this kind of illegal leaking. But there are lots of ways to distinguish Manning and Winner, and Winner still seems to be getting a sentence considerably more severe than most modern leakers. That said, if one believes that deterrence considerations are especially important and perhaps effective in this setting, perhaps it is particularly justifiable for federal prosecutors to try to throw the book at the few high-profile leakers who get convicted.

Notably, as this article notes, a federal judge has to decide whether to accept this particular plea deal with its built-in sentence of 63 months.  Comments are welcome concerning whether the judge out to have some pause about doing so.