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Jail incident 'got out of hand,' says witness in St. Louis sheriff's removal trial

St. Louis Sheriff Alfred Montgomery waits for start of the trial in the Missouri Attorney General's quo warranto case attempting to remove him from office on Wednesday, Nov. 19, 2025, at the Civil Courts building in St. Louis.
Laurie Skrivan
/
Pool via St. Louis Post-Dispatch
St. Louis Sheriff Alfred Montgomery waits for start of the trial in the Missouri attorney general's attempt to remove him from office on Wednesday at the Civil Courts building in St. Louis.

The second full day of the Missouri Attorney General’s attempt to permanently oust St. Louis Sheriff Alfred Montgomery got off to a rocky start filled with yelling, accusations of retaliation and testimony from deputies.

The testimony kicked off Thursday with testimony from a former sheriff’s office staffer who said he was trying to diffuse the situation that led to then-acting Jail Commissioner Tammy Ross being handcuffed.

Former Lt. Col. Steven Chalmers testified he was present during the Feb. 14 confrontation and, as it was unfolding, had tried to reach out to several city officials, including then-Mayor Tishaura Jones, her Chief of Staff Jared Boyd and then-Comptroller Darlene Green, to alert them of it. Chalmers said Boyd responded at a later time.

“It really just got out of hand, I thought,” Chalmers said.

When asked by David C. Mason, an attorney for the sheriff’s office, about why he felt Jones would pick up his call, Chalmers digressed about his time in politics — mentioning former Missouri Sen. Claire McCaskill and her search for a young, progressive African American to run for office.

Missouri Assistant Attorney General Andrew Clarke quickly objected, which Mason argued with until the judge stepped in.

“We’re not going down these rabbit holes,” Ohmer shouted, exasperated, during the back and forth.

“I don’t think these are rabbit holes,” Mason replied.

“Make your point with the witness,” Ohmer said, raising his voice and gesturing.

During cross-examination, Mason asked Chalmers if he recalled Ross asking sheriff’s deputies to remove the handcuffs and if Ross told the deputies to cuff her. Chalmers said he didn’t remember either and was trying to diffuse the situation.

Mason questioned if Montgomery asked Chalmers to change his report of the handcuffing incident, to which Chalmers said no.

Another sheriff’s officer, Maj. Lee Stokes, testified that Montgomery had mentioned he was going to "lock her ass up" before the confrontation with Ross. “I’m tired of her,” Stokes said the sheriff told him.

Stokes said he told the sheriff he couldn’t do that. He went on to allege that Montgomery had a track record of creating a hostile work environment and retaliated against him over a memorandum about Ross’ handcuffing and subsequent testimony to the government.

After a continued back-and-forth, tensions rose when Stokes pointed to Mason and said he was a part of the problem. Mason said he had given Stokes an opportunity to state his retaliation claims — which include losing his vehicle and not being allowed to have meetings with his subordinates.

“I was asking to be heard about retaliation, and I never got heard,” Stokes said. “[It] took half an hour to convince [Mason] that I wasn't going to attend a bogus disciplinary hearing.”

Ohmer ultimately intervened, saying they needed to focus on Montgomery and not the pair’s previous disagreements.

“I don’t want to hear this banter that has nothing to do with this gentleman over here,” yelled Ohmer as he gestured to Montgomery. He turned to Mason and continued: “Let’s move off of this and get to what we are here for. If you are trying to represent this man, do so!”

There was also testimony from Sheriff's Lt. Tyshon Sykes, who previously had the title of chief deputy and oversaw the hospital unit. He said he grew concerned about the change from 18 to eight deputies and regularly spoke to Montgomery about transports.

“It's not safe for the deputies,” said Sykes. “It's unsafe for the workers, and it puts us in high-risk situations.”

State attorneys also played audio of a phone call from Senior Deputy Jamia Abercrombie and Montgomery that Sykes had recorded with his second phone.

The audio quality made the words difficult to decipher at points, but during parts of the conversation Montgomery described what he felt were the stakes in his controversies. The sheriff could later be heard using expletives and saying that Tyshon and Lee Stokes had to go.

“This is not about me being a sheriff, this is a fight about democracy,” Montgomery told Abercrombie on the call. “My ass is on the line.”

Sykes said that after he testified to the state, he was stripped of his title, placed on administrative leave twice and stripped of his gun and badge by Montgomery.

Mason followed up during the cross-examination when Sykes said the sheriff’s office had decided ultimately not to fire Sykes and backpaid his salary for a two-week suspension he'd been put on. Mason added there is no longer a chief deputy position.

Thursday's trial also included testimony from former interim Jail Commissioner Doug Burris, who was in charge of the jail but out of the country on a planned vacation when Ross was handcuffed.

Burris said that the sheriff’s office didn’t have issues transporting detainees for medical care prior to Montgomery’s tenure and that it became an issue once he started leading the department, causing a scramble on several occasions. Only roughly a third of the jail’s staff members are weapons certified and able to complete such transports.

“Monthly there were always occasions that would happen,” he testified. “Often the phone would just ring, [and] there would be no response.”

Burris later pointed to agreements between the city and former Sheriffs Jim Murphy and Vernon Betts to transport detainees. Mason argued the documents state that such transports would have been — and can be — carried out if there were enough staff members in the sheriff’s office.

Barbara Chavers, who was recently stripped of her sergeant title, testified that she had picked up the sheriff’s kids.

Chavers at times had trouble answering some of the state counsel’s questions, including:

  • What her regular work hours were.
  • How often she used a sheriff’s vehicle to pick up the children. 
  • When she would take Montgomery’s children to school.
  • Whether the sheriff’s human resources officer told her to log her work hours.

The state had to remind Chavers a few times of the answers she gave in a previous deposition when her testimony Thursday didn’t match up.

The attorney general’s office showed photos of Chavers picking up Montgomery’s children from school in April. She said that at the time, her work hours were 6 a.m. to 2 p.m.

“I made sure it was my lunch break when I picked them up because I know they’d be hungry,” she said.

Chavers became emotional when Mason pulled up a photograph of her walking with Montgomery’s two young children. She said she prides herself on being the children’s godmother.

The day ended with body camera footage and testimony from two St. Louis police officers who were at the gas station when Montgomery had former sheriff’s deputy Daryl Wilson disarmed. The footage showed Montgomery and former Capt. Anthony Anderson confronting Wilson at the gas station.

Sgt. Lawrence O’Toole, who was present at the gas station, said Wilson’s gun was confiscated and returned to him. O’Toole testified that Montgomery said there was a person impersonating a sheriff’s deputy at the gas station. The officer’s body camera footage from that night also showed Montgomery speaking with an unnamed police officer who criticized the disarming.

“You had no right to take his gun,” the officer said. “He’s not working as a deputy sheriff.”

The trial is to continue on Friday.

This story has been updated with additional testimony.

Chad is a general assignment reporter at St. Louis Public Radio.
Brian Munoz is the Visuals Editor at St. Louis Public Radio.