The man accused of killing a deputy U.S. marshal in Tucson on Thursday night previously threatened police officers over a gun they had seized from him, according to a criminal complaint filed Friday.

Beginning April 16, Ryan Schlesinger sent emails to Tucson police officers with messages such as “Release my property or else,” the complaint said.

In one email, the complaint says, Schlesinger wrote, “The point here is that y’all need to think deep and hard about how far you’re willing to take this. Ask yourself, what are you willing to sacrifice because if my property is not returned to me, having a police cruiser repoed (sic) will be the least of your concerns.”

In July, August and September this year, the complaint says, Schlesinger went to Tucson police offices to try to arrest Sgt. Amber Kingman, who had been part of a group of officers who seized a gun from Schlesinger in August 2017.

Tucson police have been trying to handle Schlesinger’s threats and misbehavior since that August 2017 incident, Sgt. Jason Winsky testified in an August 2018 court hearing.

Winsky was among a group of officers who went to Pima County Justice of the Peace court to request harassment injunctions against Schlesinger and another man frequently seen by the Police Department’s mental health unit. Both, the officers testified, had been harassing officers assigned to the mental health unit.

At the hearing before Justice of the Peace Paula Aboud, Winsky, the head of the unit, testified: “About a year and a half ago, we started a relationship with Mr. Schlesinger with regard to threats to people at Pima Community College. My team took over the investigation, investigating both the threats and his mental health status.”

Asked by Aboud to elaborate, Winsky said, “Throughout last year (2017) Mr. Schlesinger has sent a variety of emails and voicemails. ‘You never should have crossed me. You are done in this town. I will make your life miserable.’”

In August 2017, Winsky testified, officers tried to contact Schlesinger and he barricaded himself in the house in the 2600 block of North 15th Avenue where Deputy U.S. Marshal Chase White was killed Thursday.

Marshals were trying to serve a Title 36 emergency petition to have Schlesinger’s mental health evaluated, the complaint says.

While Schlesinger was barricaded, Winsky testified, “He called 911 and said he was going to kill all the cops.”

After officers entered the house, Schlesinger tried to grab a gun, but officers stopped him, Winsky testified. They seized the gun.

“The handgun was placed into TPD evidence along with a high capacity magazine loaded with specialized ammunition designed for increased penetration,” the complaint says.

Schlesinger’s hostility toward police escalated as the year went on, according to Winsky’s testimony and the criminal complaint.

On July 3, TPD detectives interviewed Schlesinger and asked if he had access to a gun, the complaint says. Schlesinger “indicated to detectives that despite two active injunctions of harassment against him, prohibiting him from possessing firearms, he was aware that he could circumvent a background check to purchase additional firearms because he has a valid CCW,” or concealed-weapons permit, the complaint says.

Winsky testified in court that on “Aug. 21, this past Sunday he sent me individually (an email). He said, ‘it’s too bad you’ve involved my family in this beef. Now I’m going to have to involve your family in this beef.’ ”

That same day, Schlesinger went to the home of a family member where, coincidentally, Officer Dustin Dial, another mental-health unit member, was staying, Winsky testified. He also went to the home of one of Kingman’s family members.

Aboud granted the injunction against harassing or contacting the officers, which also prohibited Schlesinger from possessing firearms.

On Nov. 20, Schlesinger attempted to arrest Kingman at the west-side TPD station, 1310 W. Miracle Mile, the complaint says. On Nov. 22, he filed an online complaint in which he imagined a “shootout” happening if officers would not let him arrest them.

“At that point I have no choice but to render harmless the threat/s. I would highly recommend that the TPD arrest the criminals (officers) listed in my report so I don’t have to. I don’t think anybody wants this turning into shootout at the O.K. Corral.”

After the injunction was issued, Tucson police attempted to get an order forcing Schlesinger into mental-health treatment but failed. When he continued trying to arrest officers, they were able, though, to get an arrest warrant against him for stalking Kingman.

That was the warrant the U.S. Marshals Service was serving Thursday evening when Schlesinger allegedly shot and killed White.

“There have to be some changes made in the judicial and mental health system,” Tucson police chief Chris Magnus said. “This is just not acceptable.”

But Schlesinger’s issues with authority extend beyond the Tucson Police Department, according to records found in Pima County Superior Court and Pima County Consolidated Justice Court.

In March 2017, a Pima Community College administrator encountered Schlesinger after he was reported to have been making inappropriate comments to students in the downtown campus library. The administrator met with Schlesinger to discuss his conduct and placed him on probation until April 6, 2017.

The employee later asked Schlesinger to meet with her to discuss “continuing inappropriate communications with college staff,” but he refused to meet, saying he didn’t recognize her authority.

In late July 2017, Schlesinger sent the woman an email apologizing for the way he treated her. The email went on to say, “Consider this to be a hostile takeover. I am now in charge of Pima Community College. Seeing as I am now in charge, you’re fired.”

The email continued, “If you or anybody else has a problem with that, he/she is welcome to step into the boxing ring or octagon with me.”

A few weeks later, Schlesinger sent an “invoice” to Pima Community College, billing the school for various items, including “making me sign some (expletive) behavior contract just to continue by education at PCC.”

At the bottom of the Aug. 8, 2017 email, Schlesinger wrote, “Pay what you owe by the due date or else.”

Two days later, Schlesinger emailed the administrator again, telling her she was banned for life from Pima Community College and all affiliated events.

“Crossing me was a bad idea,” the email said.

On Aug. 17, 2017, Schlesinger hand-delivered a letter to a TPD substation, demanding that the administrator “be arrested and charged with public corruption.”

“If law enforcement fails to act, I will be forced to take the law into my own hands,” the letter said.

The administrator was notified of the letter and TPD officers said they were familiar with Schlesinger and suggested she obtain a protective order against him. The administrator applied for and was granted one the next day. Pima Community College also received its own injunction against Schlesinger.

The same day the order was granted, Schlesinger sent an email to the administrator’s supervisor, claiming that the woman was “suicidal.”

“That (expletive) tries to go to war with me … well that means she is suicidal,” the email said. “You heard of suicide by cop, well (she’s) trying to commit suicide by student or ex student I should say.”

Schlesinger was served with the injunction Aug. 21, 2017, while he was at the Crisis Response Center. He requested a hearing to dispute the injunction, but admitted to the judge during the Dec. 7 hearing that he sent the emails referenced in the administrator’s petition for the protective order.

Schlesinger appealed the decision in February, sending a six-page expletive-laced letter to the court, accusing the judge of being biased. Schlesinger said that the administrator was given more than 30 minutes to present her case but the judge refused to let Schlesinger speak after he admitted to sending the emails.

Schlesinger accused the judge of being “grossly corrupt and incompetent” and said that testimony about his threats toward the administrator were not based on evidence, but on delusion.

“My behavior has been and continues to be in retaliation to something done to me,” the letter said. “An eye for an eye. I never threatened anybody in my emails and if … PCC found my emails so harassing then there is a simple solution … Quit (expletive) with me.”

The letter mentioned Schlesinger’s dealings with TPD, saying that officers’ opinion that his behavior is concerning is based on “delusion.”

“Moving forward, anybody who believes any of my emails contain a threat is a paranoid schizophrenic as he/she would have to be reading words that simply are not there,” the appeal letter said. “I am more than familiar with the reasonable person standard and no reasonable person would interpret any of my emails to be a threat.”

The PCC administrator hired an attorney to fight the appeal. The attorney argued that the standard to obtain an injunction against harassment is fairly low and the standard was clearly met in this case.

The appeal was rejected, but the administrator reapplied for another injunction in August 2018, which was granted and still stands.

Contact reporter Caitlin Schmidt at cschmidt@tucson.com or 573-4191.

I'm a watchdog reporter covering local government, the University of Arizona and sports investigations.