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The emails were taunting, belligerent, threatening.

In the months before he shot and killed a Douglas County Sheriff’s deputy and wounded six other people, Matthew Riehl sent at least 18 different messages to officials in Lone Tree and to one police sergeant there, and Douglas County detectives combed each one to see if there were grounds for a criminal charge.

On Dec. 14, a little more than two weeks prior to the shooting, a prosecutor came back with an opinion: There wasn’t.

“We do not believe there is a likelihood of success at trial,” the prosecutor, 18th Judicial District Senior Deputy District Attorney Douglas Bechtel, wrote.

Emails between police and prosecutors, released to The Denver Post after a records request, provide new insight into Riehl’s rantings against police, the anxious effort by law enforcement officials to evaluate them and the ultimate decision not to charge Riehl.

The messages began in mid-November, after Riehl was given a speeding ticket by a Lone Tree sergeant. Riehl sent 15 messages to the municipal court in Lone Tree and another three to the sergeant, according to an investigative summary Douglas County Sheriff’s detective Phil Domenico provided to prosecutors. In the emails, Riehl accused the sergeant, without any evidence, of corruption and demanded that the sergeant be fired. He made references to “Lone Tree DSS swazi cops and a bearded judge.” He also posted at least five videos on YouTube repeating similar themes.

Gradually, though, the emails grew more worrisome for law enforcement.

Riehl included the sergeant’s home address in one email and posted it on Twitter, as well. Another made reference to the sergeant’s wife. Riehl began to demand that he be given the sergeant’s job.

“I could drive circles around you and if it ever came down to it, you know I鈥檓 a more disciplined marksman than your shaking pathetic lying ass,” Riehl wrote in one email to the sergeant.

Even as Douglas County dispatched deputies specially trained to deal with people in mental health crises to talk to Riehl, Domenico wrote that detectives contemplated a variety of possible charges: harassment, posting a law enforcement officer’s personal information on the internet, attempting to influence a public servant, witness intimidation. They weren’t sure any fit or if they rose to the level of an illegal threat, but the emails had them concerned.

“Some of the bosses both here and at Lone Tree are anxious to get that report,” Domenico wrote to Bechtel in asking for his analysis.

Bechtel’s response, though, noted that prosecutors had to weigh Riehl’s messages and the potential threat they posed against Riehl’s First Amendment rights to free speech, “especially given the wide latitude since we are public servants[.]”

In an interview, Liz Skewes, University of Colorado鈥檚 journalism department chairwoman, said Riehl鈥檚 posts and messages about law enforcement straddled a narrow line.

“It runs right up against free speech,” she said.

The First Amendment allows people to say and post bizarre things on social media. And it gives a wide berth to statements that could be perceived as threatening or offensive, she said. For there to be a crime, there must be clear, specific intent to cause harm to another person.

Determining that such a threat exists can be especially hard on social media, where people often go to vent in vivid terms, Skewes said.

“The problem for law enforcement is they can see it but they can’t arrest somebody for saying something that is not appropriate,” she said.

Bechtel wrote to Domenico that authorities might have a case if Lone Tree asked Riehl to stop sending the emails and he continued. That could show an intent to harass, instead of just an intent to vent or to get the speeding ticket dismissed.

But, in an interview, 18th Judicial District Attorney George Brauchler said any case over the emails would have been a difficult one for prosecutors, since the public has the right to criticize public officials even when those comments are crude or vile.

“Are you allowed to say that to a police officer? Yes. You’re allowed to say things like that to public officials about their public duties,” Brauchler said. “Criticism of public officials, even demeaning criticisms, is not illegal.”