The third day of the trial that could oust St. Louis Sheriff Alfred Montgomery kicked off 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 you 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 opined 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 alleged 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 unfairly prejudicing Montgomery.
“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 alleged 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 the 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 he and Montgomery did not get along, 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 did so without realizing what he was signing.
Wilson said he was no longer working at the sheriff’s office when he was confronted by Montgomery on that January 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, gave the gun back to Wilson, apologized and said they had no right to take his gun but had to do it under Montgomery’s orders.
During cross examination by one of Montgomery’s 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.
Audit
Gacinta Green, a St. Louis Comptroller’s office auditor, went over the sheriff's budget deficit and an audit released last month. Green said they had a hard time getting finances on documents to match up.
Mason asked Green why an amended response from the sheriff which claimed extensive inaccuracies in the report — including not accounting for payouts of roughly $245,000 authorized by former Sheriff Vernon Betts’s administration — was not included in the official audit. She said it was submitted too late.
Green couldn’t answer Mason's questions on if 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.
R-E-P-S-E-C-T
Sheriff Lt. Wayne Honer was with Montgomery when he ordered then-Acting Jail Commissioner Tammy Ross handcuffed.
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 an 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 and then returned to a lieutenant. When he was asked why, he said he had heard that 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. Horner 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 Missouri attorney general also said that this trial isn’t a Republican targeting a Democrat but it’s about going after an elected official she said is abusing their 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.”
This is a developing story and will be updated.
