His obsessive online posts terrorized her. But were they illegal threats?

Coles Whalen is ready to take the stage. She’d rather you not know where.

The club is small, and so is the audience: family members, friends who are longtime fans and a reporter she has invited. Suffice it to say it’s far from Denver, where Whalen says her life and career as a singer-songwriter were turned upside down by an obsessive stranger who inundated her for years with increasingly menacing online messages.

Although the trauma remains — Whalen still is reluctant to publicize her concerts — she thought the legal case was behind her. The state of Colorado charged the man with stalking, she testified against him, he was convicted, sentenced and served more than four years in prison.

But there’s a twist to the ordeal of Coles Whalen and the conviction of Billy Raymond Counterman: The U.S. Supreme Court wants to take a look at it.

The justices are revisiting a question they have failed in the past to answer, and it involves the limits of free speech. To find that a person has made a “true threat” of violence unprotected by the First Amendment, must the government show that the speaker — in this case, Counterman — intended his messages to be threatening? Or is it enough that a reasonable person on the other end — Whalen — understands them that way?

The singer is astonished that the Supreme Court revived Counterman’s appeal. On this day, she told her small audience, “We’re going through this horrible thing again.” She then offered up a new song, “Stronger,” which she’d never performed for others.

“I came back in spite of you,” she sang. “I’m not hiding anymore.”

It is more aspiration than reality. The performance was a little shaky. There were tears, onstage and in the audience.

As her friends applauded and cheered, she tried to smile. “I can’t look at anyone,” she said. “I’m not ready.”

You may have heard Coles Whalen singing if you shop at Office Depot; she was on their piped-in playlist for a time. “Butterflies” was her first national television placement: Its bouncy chorus was used in commercials for what she laughingly calls “feminine products.” She has a website, six albums, music videos. She had her biggest audience was when she opened for the rocker Joan Jett.

If you listen long enough to her Spotify channel, she said, one of the songs that might cycle through is something she was commissioned to write to accompany a series of math books for children. Now 43, Whalen has performed practically her whole life, but almost always with another job to make ends meet. She calls herself a “small artist” and frequently talks about what a musician “at my level” needs to do to stay in the game.

Perform at house concerts. Meet with fans after the show. Work the merchandise table. Publicize any and all events, and automatically accept all friend requests to the Facebook page that served as a home base for her fans.

For a time, that included Counterman. In 2010, he contacted her through her page and said he was putting together a benefit for Haitian earthquake victims. She said she responded enthusiastically. But after a few exchanges, she said, “it was clear he was not a promoter.” Their conversation ended, and she forgot about it.

Counterman began writing to her again in 2014. Over the next two years, police estimate, he sent as many as a thousand messages. “I think you’re an awesome performer, but who am I to say that you outclass many on stage,” one read. Others commented on Whalen’s looks. Some were as familiar as if they’d just seen each other.

“I am going to the store would you like anything?”

“We didn’t read every one of the messages because there were so many,” Whalen said in a conversation last month in her living room, her first interview about the experience. It was disturbing, she said, but she and others who monitored the Facebook page thought the best way to deal with it was to never respond.

Then the messages became more troubling. Counterman asked if he’d seen her in a white Jeep, which she had once owned. He asked about her mother, whom she had just visited.

Among the messages presented at Counterman’s trial:

“I’m currently unsupervised. I know, it freaks me out too, but the possibilities are endless.”

“How can I take your interest in me seriously if you keep going back to my rejected existence?”

“F— off permanently.”

“You’re not being good for human relations. Die. Don’t need you.”

“Staying in cyber life is going to kill you.”

Several times, Whalen blocked Counterman’s account. He created new ones to continue sending her texts.

She finally went to a lawyer knowledgeable about cyberstalking. “He said, “Okay, I’ll look into it,” Whalen recalled.

“I got in my car and I hadn’t driven more than a minute when he called and said, ‘I need you to come right back.’”

The lawyer discovered Counterman had been convicted and imprisoned twice on federal charges of making threats to others — the latest coming after he first contacted Whalen in 2010. The threats were much more graphic than the messages he had sent to Whalen. “I’m coming back to New York by the way, OK? . . . I will rip your throat out on sight.”

“It was just awful, direct, nasty, horrible language,” Whalen said. “I was already scared, but then I was terrified. I thought, ‘Why did I wait so long?’”

Whalen and the lawyer contacted the police, who investigated and charged Counterman with “stalking — serious emotional distress.”

When the police arrived to arrest him, he was polite and asked whether they were there because of Coles Whalen. Although they had never met, Counterman maintained that the two had a tumultuous relationship. Although she had never responded to his Facebook messages, he said she covertly communicated with him through websites such as Radio One Lebanon and Sarcastic Bad Bitches. He said she left notes for him in books at the library.

Whalen said that for months she never knew whether Counterman might emerge one night from the audience or be the person asking her to sign a CD; she had no idea what he looked like. But after the arrest, she got copies of his mug shot and distributed them to security at the venues she played. She kept a restraining order in her guitar case. She hired a bodyguard for one gig.

On the advice of a law enforcement agent, she varied her routes to work and home, and she took a class to get a concealed-carry permit and got a gun. “But I am not — I’m just not a gun person.” She replaced the gun with a pepper-spray pistol, which she still has in a fanny pack.

A low point came in Dallas, just before Counterman’s 2017 trial. She was performing for about 500 people, and she knew that Counterman could not be in the audience.

Still. “My heart starts to race. I see black spots. I can’t catch my breath,” Whalen recalled. Her friend and bandmate Kim O’Hara asked whether she was okay. “I said, ‘I don’t know what’s happening.’ I thought I might be having a heart attack.”

She sat in a chair to sing the next song and then “I left the stage. I could not go on. I couldn’t even say, ‘Sorry, guys.’ I just left the stage. It was heartbreaking. I went backstage and I cried for so long. I thought, ‘I don’t know if I can keep doing this.’”

She later learned it was a panic attack. She canceled her remaining concerts until the trial.

She attended all three days and heard Counterman’s lawyer tell the jury that Whalen and the state were, in effect, overreacting.

“The charge here is stalking,” public defender Elsa Archambault said in opening arguments. “What Bill Counterman did was annoying, but it wasn’t stalking.”

Archambault said that over those years, Counterman had never called Whalen or left her a voice mail. “He hadn’t gone to her work. He hadn’t gone to her home. For all she knew, he had never been to her shows.”

The state, Archambault said, must prove “that a reasonable person would suffer serious emotional distress. This was annoying. This was weird. It’s not stalking.”

Whalen testified and then waited as the jury deliberated. “I was thinking everyone else here is going to go on with their lives — the jury and the judge and even Kim — and to some extent this whole burden is falling on me,” she recalled in the interview. “If for some reason they find him innocent, it’s been three days of dissecting my mind, and he’s going back on the street with me, forever.”

But he was found guilty. “It was one of the most intense moments of my life. It felt like an ice-water bath over me. And they put him in handcuffs and they left.”

“Counterman has been diagnosed with mental illness,” his lawyer in the U.S. Supreme Court case, John P. Elwood, wrote in his brief to the justices. He called the messages sent by his now-61-year-old client to “C.W.,” as Whalen is referred to in court documents, “at most, heated but nonthreatening.”

“C.W. considered them menacing because Counterman’s mental illness made him unaware the conversation was one-sided,” Elwood wrote. “Because the state has not shown that Counterman knew C.W. considered his statements threatening, or even that he was aware others could regard his statements as threatening, the facts do not support conviction.”

But the justices are interested in broader issues, too. Not all speech receives First Amendment protection, the court has found, including libel, obscenity and what are called fighting words. There also is no protection of what the court calls “true threats,” although the court’s jurisprudence is as ambiguous as the term itself.

Elwood writes that the government cannot punish speech “irrespective of whether the speaker understood it was threatening.”

To not have to prove the speaker’s intent, he wrote, would be “essentially criminalizing misunderstandings.” Such an approach “chills broad swaths of protected speech, including political speech, minority religious beliefs, and artistic expression,” he added.

The Supreme Court in 2015 reversed the conviction of a Pennsylvania man who had made violent and graphic statements against co-workers and his estranged wife. Anthony Elonis posted on social media about longing to see his wife’s “head on a stick,” and fantasized about a school shooting: “Hell hath no fury like a crazy man in a kindergarten class.”

But Elonis, who also was represented at the Supreme Court by Elwood, tempered his posts by saying they were therapeutic rants. The court found that federal law required more evidence about Elonis’s intent but left the First Amendment question unsettled.

Some justices have called for the court to return to the subject. Justice Sonia Sotomayor in 2017 was troubled by a Florida case in which a man ended up in prison for allegedly threatening a store owner with a “Molotov cocktail.” He seemed to have been saying “Molly cocktail” but played along with the owner’s misunderstanding.

“Robert Perez is serving more than 15 years in a Florida prison for what may have been nothing more than a drunken joke,” Sotomayor wrote. She added that in an appropriate case, the court should “decide precisely what level of intent suffices under the First Amendment — a question we avoided two Terms ago in Elonis.”

Counterman has drawn a wide range of support. The American Civil Liberties Union, the libertarian Cato Institute, the Electronic Frontier Foundation and the Reporters Committee for Freedom of the Press are among the groups and individuals who have filed briefs worrying about how misinterpretation of communication — especially online — might undermine free-speech protections.

“One person’s opprobrium may be another’s threat,” the ACLU says in its brief on behalf of itself and other organizations. “A statute that proscribes speech even where the speaker does not intend to threaten, as does the Colorado statute at issue here, runs the risk of punishing protected First Amendment expression simply because it is crudely or zealously expressed.”

Colorado responds that its law allows judges and juries to consider context.

That includes “the broader exchange, the relationship between the person making the threat and the recipient, how the threat was conveyed, and the reaction of the intended recipient,” Colorado Attorney General Philip J. Weiser (D) wrote. “It thus effectively distinguishes true threats from political hyperbole, artistic expression, religious speech, and poorly chosen words.”

Colorado is supported by a bipartisan collection of attorneys general in 25 states and the District of Columbia, victims groups and some constitutional experts and First Amendment scholars.

And Dallas attorney Allyson N. Ho has filed an amicus brief for Whalen.

“Nothing in the First Amendment requires Counterman’s threatening messages to take precedence over Coles’ physical safety,” she writes. “If anything, Counterman’s campaign of terror silenced Coles’ own voice as an artist, a musician, and a songwriter for far too long.”

After the trial, Whalen found it difficult to put the past to rest. “So I know he’s incarcerated,” she said. “But I couldn’t shake the trauma. And I’m like, ‘What is happening? I’ve never had stage fright.’ I needed to get some help.”

A therapist told her, “I don’t know how to break this to you, but trauma doesn’t just go away.”

She said she found it hard to perform and hard to talk to fans after her shows. “You have to work so hard to keep yourself relevant at my level,” Whalen said. “I started canceling shows; I didn’t travel as much. Kim had to find another job. It was not long before the momentum began to stall.”

She decided to concentrate on the other parts of her life, “but a new life is hard to find.” Her sister Marita came over to look through her closet. “You don’t even have any real clothes,” Marita told her. “You have show clothes and road clothes.”

Whalen was offered a job in marketing on the other side of the country, and she took it, intending that it be temporary. But something unexpected happened: She met a man, fell in love and got married. They now have two young children.

Whalen wants to stay in music, and her husband is supportive. “He says, ‘It’s only going to take one hit, babe, and we can send our kids to college!’” she said.

She performs occasionally, sometimes putting the events on her website or sending her fans notice through email lists. She recorded an album in 2021 but did little to promote it. “That was just for me,” she said.

“I do feel like I want to write another album and feel like I want to help it get exposure,” she said. But it’s hand in hand: If it gets exposure, I personally get exposure. There’s no way to separate the two.”

Her new song, “Stronger,” would be part of that. The Supreme Court hears Counterman’s case this month. Sometime after that, Whalen would like to travel to Nashville, where she once lived, to record the song.

Her first attempts at writing it were terrible, she said, full of cliches and empty phrases.

“I’m still mad that I even have to find a way to tell people how difficult it was,” Whalen said. But she realized that what she wanted to say was simple.

“I’m just trying to say I went through this horrible thing and I made it to the other side, with a lot of clawing and work,” she said. Those who meet her now will never know the old version of her. “I’m a new me, but I can still perform if I want to.”