The third day of the trial that could oust St. Louis Sheriff Alfred Montgomery kicked off Friday with concerns from Circuit Judge Steven R. Ohmer when the state asked to admit federal records as exhibits.
“He does not need to put that in evidence,” said sheriff’s staff attorney David C. Mason when Missouri Assistant Attorney General Gregory Goodwin asked for the sheriff’s indictment to be admitted along with his arrest order. “What he's doing your honor is very passively … showboating — bringing this out to embarrass Mr. Montgomery.”
The sheriff, wearing a blue blazer, striped gold tie and gray slacks, wiped away tears with a napkin. Ohmer said shortly after that the materials would be submitted and that it was important to remember they don’t prove or disprove anything at this point. He did have thoughts about the potential showboating.
“It doesn’t impress this court at all, and that kind of tactic is counterproductive in this court's opinion,” said the judge. “I’m not a jury, and it may come back to bite you if you try to do stuff that isn’t necessary.”
Ohmer said he is confident the court can juggle the different elements of the case without prejudice.
“This court’s very concerned about this interplay of the […] federal procedure and this court,” he said. “It’s very unusual and disturbing, frankly, to this court.”
Disarming Darryl Wilson
The day’s witnesses included a former sheriff’s deputy who said Montgomery made him give up his personal firearm while working security.
Montgomery maintained that Darryl Wilson was impersonating a sheriff’s deputy at a gas station convenience store where Wilson worked a second job. Montgomery had also said Wilson wasn’t wearing an adequate security uniform or a visible identification card.
Wilson, who said he was taking classes to become a peace officer, detailed a tense relationship with the sheriff. He said that he and Montgomery did not get along and that the sheriff switched Wilson's schedule and interfered with his officer training classes. Montgomery allegedly told Wilson that he either had to drop out or be fired, and when he refused, the sheriff forced him to sign a resignation letter. Wilson said he didn't realize what he was signing.
Wilson said he was no longer working at the sheriff’s office when he was confronted by Montgomery that night. Wilson said he called St. Louis police after he was told to give up his gun or risk arrest.
After police arrived, then-Sheriff’s Capt. Anthony Anderson, who was with Montgomery, reportedly gave the gun back to Wilson, apologized and said they had no right to take his gun but had to do it on Montgomery’s orders.
During cross-examination by Montgomery lawyer Matt Ghio, Wilson confirmed he had been verbally reprimanded for not wearing the proper security uniform. Wilson also said he had his security license but couldn’t recall if it was visible on his outerwear.
Money problems
Gacinta Green, a St. Louis comptroller’s office auditor, went over the sheriff's budget deficit and an audit released last month. Green said it was difficult to get finances on documents to match up.
Mason asked Green why an amended response from the sheriff that claimed extensive inaccuracies in the report — including not accounting for payouts of roughly $245,000 authorized by former Sheriff Vernon Betts’ administration — was not included in the official audit. She said it was submitted too late.
Green couldn’t answer Mason's questions about whether she was aware of tensions between the administrations. Green said the sheriff’s office requested an audit in January but didn’t cooperate with her office.
The largest expenses in 2025, Green said, were for a new Chevrolet Tahoe, uniforms and badges purchased under Montgomery’s administration.
In the audit, it was found the sheriff’s office did not have the proper accounting controls and procedures. One of those instances came to light during sheriff’s office Col. Yosef Yasharahla’s time as interim sheriff. He recalled there was a mega-land tax sale — a result of four sales that had been postponed due to the May 16 tornado — that ended up netting approximately $1.4 million in cash laying out in the office.
Leonard E. Bell Jr., a city comptroller internal auditor who helped count the cash, later said it was over $2 million.
“It was more money than I have ever seen,” Yasharahla said. “It was everywhere.”
Yasharahla said he immediately called “the treasurer, comptroller, the mayor — everyone” in order to get auditors to help count the money. Taking cash in land tax sales was confusing, he said, and he believed Betts had started the practice.
Bell testified that his division has never before helped count cash from land sales — and that there’s missing money.
“We have found at this point that there is $39,738 that we cannot trace [...] to the validated deposit slips,” he said. “It is missing at this point. [...] The internal audit section has never had that irreconcilable amount in land tax sales.”
Bell said the number of those discrepancies have been historically low over the years he’s been working in the auditing department.
He doubted that the sheriff's office’s deficit was a result of Montgomery’s leadership.
Tashana Syas, the sheriff’s former director of personnel and fiscal operations, said she was a “stickler” for following the appropriate procedures.
She said she grew concerned with how the department was handling its funds and didn’t want to approve certain expenditures like vehicles and badges. She said Montgomery came to her and told her to sign off on new Chevrolet Tahoes from south St. Louis-based Don Brown Chevrolet, but she knew it would reflect that they didn’t follow the proper procurement process.
“I also hid in the bathroom for 45 minutes before signing the check,” she said. “It was overwhelming.”
The money for the purchase came from concealed carry funds — a separate pot of money that had nothing to do with vehicle purchases, she said.
Syas is suing the sheriff’s office and the city and has claimed that the sheriff’s office fired her in retaliation for cooperating with the federal investigation in the sheriff. Mason and Syas went back and forth on whether she'd told federal authorities to listen to employee review hearings, parts of which were played during the trial. Syas called that hearing an interrogation.
Yasharahla disagreed. He said he had many concerns about how she interacted with the sheriff’s staff, despite her being technically good at her job.
“I asked her [after] if she could do it all over again, would she treat them a little better? She said no,” he said.
The sheriff’s office has said that Syas was fired for shredding documents around 3 a.m.
Mason, the sheriff’s attorney, peppered Syas about the documents, which she said had contained protected employee information and had been scanned in before she shredded them. She added that they were not legal in nature.
“We don't know what documents you shredded,” Mason said. “We can't tell if they're documents that make you look bad.”
Yasharahla told the court that the office had told Syas not to shred anything due to the federal investigation into the sheriff’s office.
“I did the right thing to protect employee information,” Syas said on the stand. “I am aware of the legal holds and respected [the] legal holds.”
The sheriff's office fired Syas shortly after that incident.
R-E-P-S-E-C-T
Yasharahla recalled the day then-acting Jail Commissioner Tammy Ross was handcuffed at Montgomery’s orders.
“I was hollering, ‘Stop,’” he said, adding he was disappointed he couldn’t diffuse the incident. “I was just disturbed about the whole situation.”
Yasharahla said that the handcuffing confrontation appeared to be weeks in the making, mentioning a few instances in which where Ross allegedly cursed at Montgomery. He said he’d met with her along with Maj. Lee Stokes and thought their tension was resolved.
The state introduced an interview between Montgomery and KSDK’s Mark Maxwell.
“If anyone impedes on the duties of the sheriff’s office, yes, we’ll take them into custody,” the sheriff tells Maxwell in the interview. “I can’t save the world, but I can save the city.”
Sheriff's Lt. Wayne Honer was also with Montgomery when he ordered Ross’ detention.
Honer said the sheriff told him to write a report on the Ross incident and was later asked to revise it after Montgomery ran it through artificial intelligence software. The lieutenant testified he signed the revised report when asked but did not do the revisions himself and stood by his original report. He said he’d never been asked to lie in reports.
The sheriff demoted Honer at one point, who was then returned to a lieutenant. When he was asked why, Honer said he had heard that he was given a loyalty test.
Honer was also asked about a printing snafu that resulted a new sheriff’s emblem being installed on the wall outside their office with the word “respect” misspelled “REPSECT.” The same error was printed on several shirts handed to deputies. However, Honer told the court that the printer made the error and subsequently corrected it.
Hanaway in the house
Heads turned as Missouri Attorney General Catherine Hanaway walked into the courtroom room shortly before noon.
Speaking to the press at the lunch break, Hanaway said she’s confident in the case her staff is presenting. “None of our witnesses have been hurt on cross-examination,” she said. “So we’re feeling cautiously optimistic."
Hanaway pushed back on Mason’s claims earlier in the week that the sheriff’s children being transported amounted to a nothingburger.
“In the modern world when mom and dad work, kids do end up at the office for short periods of time — but not every day, not a very regularized basis,” she said. “It’s not build into the scheme of how you provide child care.”
Hanaway said her office would still be willing to cut a deal if Montgomery voluntarily resigns.
“I know that we would be completely satisfied,” said Hanaway. “We would completely go away if he would step down.”
The attorney general also said that this trial isn’t a Republican targeting a Democrat but about going after an elected official she said is abusing the office.
“We have filed quo warranto actions all over the state — including in very small, majority-white areas — against sheriffs and prosecutors who aren’t doing their jobs,” she said. “We’ll continue to do that wherever we see the taxpayers and the state and the citizens being harmed.”
After Friday’s hearing, Mason said that the counts don’t amount to removing Montgomery.
Mason pointed to Montgomery’s conversation with STLPR last month in which he called the attacks against him racist. When asked if the sheriff feels remorse, Mason said that the sheriff has learned a lot.
“When I talk about that, he's learned, it isn't so much remorse as recognition,” Mason said. “Recognition that there's some maybe different or better steps.”
The trial continues on Monday.
This story has been updated with additional testimony.
