St. Louis Sheriff Alfred Montgomery finally had his day in court after a short delay.
The sheriff’s attorney struck a deal with the federal government late Tuesday to allow Montgomery to attend the state removal trial after Circuit Judge Steven R. Ohmer expressed concern about the fairness of a trial otherwise.
Montgomery is being held at the Perry County Jail in Illinois — roughly 100 miles southeast of St. Louis — for violating the conditions of his bond in a separate federal case.
Montgomery walked into the courtroom wearing a dark charcoal suit and light blue tie but without shoelaces. The sound of the sheriff’s shackled hands and feet rattled through the courtroom as he slowly walked to the defense’s table. Two U.S. marshals stood guard on either side of him.
Montgomery was mostly stoic except for a few tears welling from his eyes, which he wiped away before the trial started.
Opening arguments
The trial began with Assistant Attorney General Gregory Goodwin arguing a summary of each of the six charges against Montgomery.
Goodwin also alleged that the sheriff had staff fabricate reports with the help of artificial intelligence about an incident in which Montgomery ordered acting jail Commissioner Tammy Ross handcuffed.
When a deputy refused to do so, the state alleged Montgomery stripped the deputy of their title and pay.
David C. Mason, one of Montgomery’s attorneys, pushed back on the anecdotes, arguing reality wasn’t as extreme as Goodwin made it sound.
“Was the final report truthful?” posed Mason. “Yeah, he may clean up language using the AI thing — so what? It’s not changing facts.”
Mason and the attorney general’s office sparred over if the counts brought forth were extraordinary enough to call for the elected sheriff’s ouster. Yet, Goodwin said the violations “either individually, and certainly collectively, justify a permanent order of removal.”
Mason disagreed.
“In order to rise to the level of justifying quo warranto, there has to be evidence that the conduct was so extreme in nature that a huge should remove duly elected official,” he said while defending Montgomery having a sergeant drive his children around “because it’s a common practice.”
Transport troubles
The state brought Ross, the longtime deputy jail commissioner, as its first witness. Ross talked about the long practice of the sheriff’s office transporting jail detainees to get medical care — something Montgomery refused to do.
“If the sheriff’s department notifies us they’re unavailable, our office has to transport,” Ross said, noting it became a strain on the facility’s already low staffing and detainee’s services.
The deputy commissioner later recalled her first interactions with the sheriff, just a few weeks after being sworn into office. Ross testified of telling Montgomery that if he needed to access the facility to contact her, she would make it happen. But, she noted, all things didn’t seem right with his reaction. “To me, there was a look of arrogance, a look of entitlement,” said Ross. “So, that’s how I felt when communicating with him.”
Mason, the sheriff’s attorney, cross-examined Ross and pointed to a contract between the city and Puerto Rico-based medical contractor Physician Correctional USA — an agreement that doesn’t include the sheriff’s office. The state objected on relevance, which Ohmer overruled.
The cross examination became tense when Mason asked if the contracted doctors are corrections officials. The sheriff’s attorney and deputy commissioner squabbled so much that the judge had to step in.
“Just answer the questions,” said Ohmer, turning to the deputy commissioner. “Don’t think about what he’s asking. Just listen and answer and don’t start rambling.”
A handcuffing dispute
Much of Ross’ testimony revolved around the circumstances around her handcuffing at the behest of the sheriff.
The incident stemmed from an allegation that former Deputy Sheriff James Short sexually assaulted a detainee in January. The deputy was subsequently arrested.
Linda Mopkins, a recently resigned internal investigator for the sheriff’s office, said Montgomery asked her to look into the alleged assault. Montgomery’s attorneys said the sheriff’s department’s internal investigators asked Ross at least three times to interview the victim for their own internal investigation. Ross confirmed she got the requests.
“I needed to get approval from the Department of Public Safety and legal department,” testified Ross. “I said it because I think it’s the right thing to do. I don’t know what [their] intent was, I don’t know if it was tampering. I don’t know if it was anything of that nature.”
Mopkins said she felt Ross was cooperative with her efforts in interviewing the detained woman, though the process was slow-rolled by then-City Counselor Sheena Hamilton despite it being a time-sensitive matter.
While Mopkins was ultimately able to conduct her interview, Ross said she had additional doubts if it was necessary for the detainee to be interviewed by the sheriff’s office: “My concern is her well-being and her mental health.”
Justin Gelfand, one of the sheriff’s attorneys, said it wasn’t Ross’ call to allegedly impede the sheriff office’s internal investigation.
After Ross declined to allow the sheriff’s investigators for the third time, Montgomery appears to have confronted Ross, according to a security video played in court.
The video, presented by the state, shows a confrontation between Montgomery and Ross on Feb. 14 as two other deputies inch toward her. Eventually, they turn her around and put her in handcuffs and march her away. The sheriff is seen with his hand on her back as they move Ross through the halls to a back office on the side of the jail he controls.
Ross said Montgomery made several threatening statements at that point and said he was going to hold her for 48 hours. The deputy commissioner said she believed she was arrested during the time that she was handcuffed.
“I didn’t know that you had arresting powers,” Ross recalled telling the sheriff, to which he reportedly replied: “There’s a lot you don’t know about me. You guys are going to find out.”
She said former public safety director Charles Coyle spoke with the sheriff over the phone and said if Montgomery was going to enforce unknown laws, he would have to put them in writing. Ross said then-sheriff’s attorney Blake Lawrence whispered something into Montgomery’s ear, and they released her. The evidentiary video shows the deputy commissioner walking back to her office about being released.
Ross said since Montgomery has left office, detainees have been transported to the hospital as they were under previous administrations. A court order is requiring such transports to occur.
A gas station confrontation
Anthony Anderson, the former sheriff’s captain over secondary employment, took the stand to testify about the night he and Montgomery confronted former Deputy Darryl Wilson at a south St. Louis gas station.
Montgomery had gotten word that Wilson was impersonating a deputy, Anderson said, so the pair went to investigate. When they arrived they found Wilson wearing a beanie with “security” sprawled across it — but when they arrived, the rim of the hat was flipped up so you couldn’t read it.
Anderson said Montgomery asked for Wilson’s weapon in order to ensure their safety and because there was workplace tension between Wilson and Montgomery. The former deputy refused to hand his weapon to the sheriff and instead gave it to Anderson as Montgomery called the police, he testified.
The former captain said he was terminated after he injured his back. He recalled lying on the floor of his home when the termination letter was delivered. Throughout his testimony, Anderson trembled and winced in pain as Ohmer comforted him periodically.
Anderson spoke to the owner of the gas station and the security company Wilson said he was working for as part of the investigation. He said the gas station owner did not know Wilson was not actively employed with the sheriff’s department, and was paying Wilson a higher amount. The security company owner Wilson said he worked for said the gas station wasn’t one of its approved security posts.
The former captain said at the conclusion of his investigation, he presented his findings to St. Louis Assistant Circuit Attorney Sean O'Hagan, who declined to charge Wilson. Ohmer asked what charges Anderson had asked for.
“My main thing was he was obtaining more money than a regular security officer,” Anderson said, replying that he’d requested a warrant for stealing.
Anderson said he had not done that before as a sheriff’s office employee, but it was typical practice when he served as a police officer. He said he didn’t follow up after O’Hagan’s denial because he “just wanted to get it off my back” and “back in the hands of the sheriff and his attorneys.”
The state has said the reputed incident demonstrates Montgomery has attempted to enforce criminal law, violating state statute.
Mopkins, the sheriff’s former internal investigator, said she declined to investigate the Wilson matter because he was no longer an employee of the sheriff’s office. After that, she said, she was reassigned in the department before deciding to resign.
The case continues on Thursday and is now expected to go into next week.
