By Jess Bravin 

WASHINGTON--A case before the Supreme Court over threats made on Facebook is highlighting long-standing tension between law enforcement and free-speech advocates over when threatening speech crosses a line and breaks the law.

The appeal, up for arguments on Dec. 1, presents a vexing legal issue courts have long struggled to settle, and it does so when what people say can reach a bigger audience than ever before through social media. Although social-media companies have rules for managing individual speech online, the outcome could affect the leeway people have to express themselves, even darkly and violently, on Facebook, Twitter, YouTube and other sites.

Prosecutors have brought a string of cases alleging that serious threats posted on social media deserve jail time. Lower courts have split over whether the government must prove a person actually intended to threaten someone--or merely that a "reasonable person" would perceive that he or she did so in their online post. Free-speech advocates argue the Constitution gives people wide latitude for expression, and that a ruling allowing the "reasonable person" standard would chill legitimate speech on social media and elsewhere.

John Elwood, the Washington attorney who will argue on behalf of Anthony Elonis, a Bethlehem, Pa., man who was convicted of threatening his estranged wife in a series of Facebook posts, said his client's posts can be likened to songs such as "Kim" and "Kill You" from Eminem's Grammy-winning "The Marshall Mathers LP," where the artist sings about killing his then-wife and mother.

Mr. Elwood said Mr. Elonis was only venting frustration after a run of personal setbacks, including the collapse of his marriage and the loss of his job at the Dorney Park and Wildwater Kingdom amusement park in Allentown, Pa. If Eminem "were still playing 250-seat gyms, it would be hard to distinguish him from the heartbroken amusement-park worker here, who also had an audience of about 250 people," he said.

The Justice Department declined to comment, but in a legal brief it said that fears of limiting legitimate speech are overblown. "The reason that [Mr. Elonis] can confidently cite the rapper Eminem's lyrics as examples of art, rather than threats, is that no reasonable person would understand those lyrics, in the full context in which they were delivered and publicized," to constitute an intentional threat of violence. If prosecutors should overstep, "juries are fully capable of distinguishing between metaphorical expression of strong emotions and statements that have the clear sinister meaning of a threat," the court brief said.

Following separation from his wife, Mr. Elonis began posting violent statements on Facebook, the first announcing "sinister plans for all my friends." His wife became a particular target. "If I only knew then what I know now, I would have smothered [you] with a pillow, dumped your body in the back seat, dropped you off in Toad Creek, and made it look like a rape and murder," said one post.

Mr. Elonis served just over three years in federal prison after being convicted of posting threats.

Federal law shields online companies from liability for statements posted by users, a restriction that has given social-media companies room to let people speak relatively freely.

Facebook isn't named in the case but is following it. A spokeswoman for the Menlo Park, Calif.-based social network declined to comment on the particular case or the issue of threatening posts generally.

However, in its published "community standards," Facebook says that "we remove content and may escalate to law enforcement when we perceive a genuine risk of physical harm or a direct threat to public safety. You may not credibly threaten others, or organize acts of real-world violence." The policy adds "that something could be disagreeable or disturbing to you without meeting the criteria for being removed or blocked," and for that reason the website provides users "the ability to hide or quietly cut ties with people, pages or applications that offend you."

The Reporters Committee for Freedom of the Press and several other media organizations said in a court brief that the Supreme Court should continue to give disagreeable expression broad First Amendment protection. "Public commentary is frequently meant to provoke--whether by urging listeners to rethink their position on an issue or to take action--and this country has a long history of protecting provocative speech," the brief said.

In 1969, for instance, the Supreme Court threw out the threat conviction of a draft resister who proclaimed, "if they ever make me carry a rifle, the first man I want to get in my sights is LBJ," at a 1966 antiwar rally. The court said the speech was clearly "political hyperbole," perhaps "vituperative, abusive and inexact" but nonetheless constitutionally protected.

The digital era has upended traditional expectations, however, making it far easier to disseminate communications while often stripping them of the context that could make their significance clearer.

"What's potentially new about social media is the possibility that speech will slip from one context to another," says James Grimmelmann, a University of Maryland law professor.

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