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Former staffer says St. Louis sheriff didn’t order then-jail boss’ handcuffing

Missouri Attorney General Andrew Bailey included this exhibit of St. Louis Sheriff Alfred Montgomery detaining at-the-time acting City Justice Center Commissioner Tammy Ross at the City Justice Center last February.
Missouri Attorney General's Office
Then-Missouri Attorney General Andrew Bailey included this exhibit of St. Louis Sheriff Alfred Montgomery detaining Tammy Ross, who was the acting corrections commissioner, at the City Justice Center in February.

Former Master Sgt. Bryan Robins said he remembers the day he helped Lt. Wayne Honer place handcuffs on then-acting jail Commissioner Tammy Ross.

On the fourth day of the trial that could remove St. Louis Sheriff Alfred Montgomery, Robins recalled believing a confrontation between Ross and Montgomery was getting out of control. He called for the sheriff’s office’s top brass to assist but was “upset when I was calling for help [and] no one responded.”

Video evidence shows that other staff did eventually show up. Robins was tasked with providing security for the sheriff and managing his day-to-day scheduling.

When Robins arrived, he saw the sheriff and Ross arguing. Robins said he heard Ross say something like “go ahead and ‘cuff me.'” When Honer pulled out his handcuffs, Robins said he helped Honer place the cuffs around Ross' wrists because “handcuffing is dangerous.”

Robins said he did not recall hearing Montgomery giving orders to detain Ross.

“I was upset with everything that happened,” he said in the second week of a Missouri attorney general-led bench trial that could oust Montgomery from office. “I was embarrassed [for] arresting Tammy Ross with no reason why.”

Moving on to claims of retaliation, Robins recalled Montgomery referring to Tashana Syas, Tyshon Sykes and Lee Stokes as “the three” — people who allege they were retaliated against by the sheriff’s office for cooperating with federal authorities. Syas is suing the sheriff’s office, claiming retaliation.

David C. Mason, the sheriff’s staff attorney, doubled down on his assertion that the three individuals had not been retaliated against, mirroring his arguments from last week, and saying that disciplinary actions were not taken against Sykes and that Stokes didn’t face an employee review committee.

Mason said again in court that Syas was fired for shredding documents in the dead of night. While Robins said he, at one point, was standing in a courthouse bathroom with a translucent garbage bag filled with shredded documents, Judge Steven Ohmer cut off the line of questioning, saying it wasn’t relevant.

Robins also told the court that Honer was demoted because Montgomery believed Honer was also working with federal authorities before realizing he wasn’t and subsequently promoted him back to lieutenant. Honer confirmed the back-and-forth in rank last week — but said he believed he had been demoted as a so-called loyalty test.

After the Missouri attorney general’s office rested its case, Mason told the court there wasn’t sufficient proof to immediately remove Montgomery from office.

“I started the case telling the court there would be a failure of truth,” said Mason. “This case does not meet sufficient enough proof to warrant [a] quo warranto moving forward.”

Ohmer declined to immediately remove Montgomery at that point and allowed the sheriff’s office to present its witnesses after.

Court documents show St. Louis Sheriff Alfred Montgomery and former Capt. Anthony Anderson confronted Darryl Wilson outside the Phillips 66 at Kaiser Grand Market — questioning why he was working a security post meant for an active-duty deputy. The gas station and convenience store, located in the city’s Dutchtown neighborhood, is pictured Tuesday evening.
Brian Munoz
/
St. Louis Public Radio
Court documents show St. Louis Sheriff Alfred Montgomery and former Capt. Anthony Anderson confronted Darryl Wilson outside the Phillips 66 at Kaiser's Grand Mart — questioning why he was working a security post meant for an active-duty deputy.

Kaiser’s Grand Mart

Chad Kaiser, a majority shareholder of Dutchtown-based gas station and mini-mart Kaiser’s Grand Mart, testified he wasn’t aware Darryl Wilson was no longer employed by the sheriff’s department on the night he was disarmed.

Kaiser added that his business does not use security guards and specifically uses law enforcement working a second job.

The gas station owner said Wilson never informed the third-party security company he used that he had resigned — or was forced to resign — from the sheriff’s office.

Christopher Smith, the owner of Gateway Security Services, also said he’d never placed guards at the gas station in question though he’d hired Wilson for other jobs.

“We were concerned because we saw that our company’s name was mentioned in the news,” he said, adding they reached out to the sheriff’s office to figure out what was going on. “At that time, Mr. Wilson was no longer with our company.”

Mason pointed to the differences in pay between a law enforcement official working a secondary shift and a private security guard — $50 or so an hour for the former and roughly $20 for the latter. The sheriff’s attorney said that Wilson had duped the security company for additional pay and that it was within the office’s right to investigate the matter, even though Wilson was no longer on staff.

St. Louis Sheriff Alfred Montgomery, center, talks with his attorney Justin Gelfand on Monday, Nov. 24, 2025, before the start of the trial in the Missouri Attorney General's quo warranto case attempting to remove Montgomery from office in the Carnahan Courthouse building in St. Louis.
Christian Gooden
/
Pool via St. Louis Post-Dispatch
St. Louis Sheriff Alfred Montgomery, center, talks with his attorney Justin Gelfand on Monday before trial resumed in the Missouri attorney general's quo warranto case attempting to remove Montgomery from office in the Mel Carnahan Courthouse in St. Louis.

More phones, more money, more problems

Mason pulled out three black flip phones while sheriff’s Capt. Dan McGinnist was on the stand.

The sheriff’s attorney said he objected to the use of “burner phone” to describe the phone Montgomery allegedly used to harass federal witnesses. He said that terminology had connotations involving drug dealers and that, in fact, the sheriff was using a standard office phone.

Assistant U.S. Attorney Christine Krug sat in the back of the courtroom and shook her head as Missouri Assistant Attorney General Greg Goodwin examined the trio of phones.

Ohmer ultimately shut down the argument.

Attorneys also argued the details of an October land tax sale — and what was last week testified to be about $40,000 of unaccounted-for money out of roughly $2 million in cash spread throughout the office from a land tax sale. Stacey Jennings, a sheriff’s office accounting clerk, testified she believed the missing amount was closer to $28,000.

Justin Gelfand, an attorney with the sheriff’s office, contended that there actually wasn’t money missing and that the accounting discrepancy is because some purchasers did not pay for the parcels they acquired that week. The purchase verification process, Jennings said, doesn’t have to be completed for another week and a half.

Monday’s court session included extensive testimony that rehashed last week's, including the city comptroller’s audit, the results of various staff employment review committees, if there’s ever been a directive to deny transporting prisoners for medical care, compensatory time payouts and then-Sgt. Barbara Chavers transporting of Montgomery’s kids to and from school.

Mason argued “there was no evidence that the kids sitting there interfered with government services” and “since there was no cost, there was no benefit.”

Maj. Doug Clark, the warden at the Perry County Jail, was the defense’s final testimony of the trial. He said that Montgomery has access to a phone from 8:30 a.m. to 2 p.m. He also has texting available via an iPad 24/7 while held at the southern Illinois facility — as long as he has money in his account.

Closing arguments in the trial are set for Tuesday morning.

This story has been updated.

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