A veritable who’s who of those who feel wronged by St. Louis Sheriff Alfred Montgomery gathered at an hours-long hearing Wednesday to see whether a bill to set the duties of the Sheriff's Office would be immediately enacted.
Board Bill 33, signed into law by Mayor Cara Spencer earlier this week, requires the Sheriff's Office to transport jail detainees to receive medical care and submit to yearlong financial monitoring.
Lawyers for the city responded to a temporary restraining order the sheriff filed Monday against the law going into effect with their own TRO request on Tuesday afternoon, asking the judge to immediately enact the bill because the responsibility of transporting detainees for medical care has “been performed by the sheriff’s department for decades.”
Montgomery’s predecessor, ex-Sheriff Vernon Betts, and St. Louis’ deputy jail commissioner Tammy Ross took the stand to testify about the inner workings of the sheriff’s office, the city jail and the impact that Montgomery’s tenure has had on the jail.
Joe Neil, Ross’ attorney, Corrections Commissioner Nate Hayward and various city staffers cold be seen popping in and out of the courtroom through the hearing.
After nearly 5 hours of arguments from the sheriff’s attorneys and the city, Circuit Judge L. Moriarty said she would rule on the matter at a later time.
Medical transports
The heart of the argument between the parties lies with the question: Is the sheriff duty bound to do medical transports?
David Mason, an attorney representing the Sheriff's Office, argued the city cannot order an independently elected official to hire more deputies — or reassign them from other areas — to complete an unfunded mandate.
“[The city] is going to actually look this court in the face and say: ‘You should make [the Sheriff's Office] do something that we’re not sure they’re even capable of doing,’” Mason said.
Mason referenced a 2004 assistant city counselor’s memorandum stating there needed to be a formal agreement between the Sheriff's Office, the Department of Corrections and City Hall on the task — to which Associate City Counselor Erin McGowan objected.
“I’m surprised the city wants to avoid its own counselor’s words,” Mason retorted. “I can’t blame them because it goes against its present day motion.”
Mason said that just because previous administrations did so doesn’t mean the sheriff is required to. If so, then “every elected official is hereby bound by everything the previous elected official has done,” Mason said. “That is not [just for] this elected official — for the recorder of deeds, for the comptroller or for everyone else.”
Col. Yosef Yasharahla, a long-time sheriff’s department employee and second in command to Montgomery, testified that when deputies have been pulled from other areas — including court security — when required to medically transport detainees. The issue came to a head in 2023 when the 22nd Judicial Circuit’s bench said they were poised to hire their own courtroom security due to staffing issues under former Sheriff Vernon Betts.
The undersheriff said the office would have to re-establish the so-called “jail unit” — and receive funding to support it — in order to carry out all medical transportation of jail detainees as outlined in the bill.
“If we have to take on this task, we have to leave the circuit without the security. We have to leave the voters, which is the jurors, without security,” said Yasharahla. “It’s just a tragedy waiting to happen.”
Yasharahla said as such in an email sent last Thursday submitted by the city in attempts to show the department acknowledged a responsibility to spearhead medical transports. The email also asks for a two-week minimum notice for the Sheriff's Office to transport jail detainees to medical appointments.
The undersheriff went on to say this isn’t a new policy, but rather a clarification that this has been the long-time policy — despite the subject line of the email reading “New Policy on Prison Transportation for CJC."
When asked about the apparent policy change during a break, Betts scoffed.
"That's stupidity because you can't determine who's going to be sick, and how sick they're going to be, or what incident might take place at the Justice Center," he told reporters. “You have to have a staff that's ready to go at a drop of a hat, and that's what we always had."
Locked inside
Mason peppered Ross, St. Louis’ deputy jail commissioner, with questions related to the city’s contract with the jail’s medical provider and staffing.
As of Wednesday, Ross said the jail was short staffed — only 75 of 133 allocated correctional officer positions are filled amid multiple resignations in the last three weeks.
When transporting detainees, Ross said the jail’s policy is to send one firearms-trained employee with additional corrections officers. The jail only has 27 staff who are firearms trained so they have historically relied on the Sheriff's Office or calling in ambulances when the medical provider deems necessary.
The sheriff’s refusal to do medical transports has put the CJC staff on edge, the deputy commissioner said.
“It’s already a stressful job. It’s requiring them to work additional hours [and] this contributes to turnover rate,” Ross said. “We’re already having issues with staffing.”
The policy has also taken a toll on jail detainees, she said.
Ross said when she has had to pull officers from directly working with detainees, it has led to reduced or modified services including: limited shower time, shortened length of phone calls and reductions in opportunities to participate in rehabilitation or educational programs.
“These things are happening. They’re not speculative harms,” she said. “It’s important they have time outside their cells.”
Ross is also suing Montgomery over his order to have her handcuffed earlier this year. The action also got the sheriff federally indicted last month.
Old grudges
Betts, the former sheriff, took the stand to outline the duties of his old office — including transporting detainees for medical care.
Across the courtroom, Montgomery locked eyes with his predecessor, who now works as a security guard for a downtown data center. The two men have rarely shared a room since their bitter contest.
Mason pressed Betts on whether he had ever signed a formal agreement requiring the Sheriff's Office to handle medical transportation. Betts said there had been “a lot of discussion” with the jail over the years but added, “I don’t know if I ever [...] signed any kind of formal agreement.”
When talking to reporters earlier in the day, the former sheriff said he also faced financial challenges when leading the department. "We did whatever you need to do when you have a business, and you got to get the job done, he said. “Then you have to use resources from other places."
The line of questioning quickly shifted to comments Betts had made about Montgomery. Asked if he ever called for Montgomery’s ouster, Betts said no — until Montgomery’s attorneys played a KSDK interview in which Betts says, “I think it’s about time. I think Mr. Montgomery has done enough that he’s not qualified for the position."
”That’s you in the video?” Mason asked.
“Yes it is,” Betts replied. “All true.”
The city’s attorney, McGowan, objected and questioned the video’s relevance. She noted the two men are political rivals.
Despite stating otherwise in his afternoon testimony, Betts told reporters earlier in the day he would be interested in returning as sheriff if Montgomery was removed by the attorney general.
“I would be interested in coming back just so that we could get this train back on track,” he said. “I would be willing to do that for the next three years, and then we’d call it a day.”
Closing arguments
The city and Sheriff's Office both doubled down on their positions.
McGowan refuted the Sheriff's Office’s claims and said they do not meet the extraordinary threshold for a temporary restraining order.
“Today, the Sheriff's Office is seeking a TRO so he doesn't have to do his job,” she said. “He didn’t support his assertion with facts. He didn’t provide any incidents of irreparable harm. Here, the status quo is the Sheriff's Office has been transporting medical inmates for decades.”
She argued that the city does have the authority to pass laws around the duties of the Sheriff's Office due to language in the state constitution around city’s authority.
“The fact here is that the duty is one that has been performed by the sheriff’s department for decades,” McGowan said. “It’s not in the public interest that the Sheriff's Office does not have to do its longstanding job of transporting jail detainees to medical appointments.”
Mason said immediate enactment of Board Bill 33 “would have a serious and detrimental impact” on providing safety and security for the court buildings and in effect, the Board of Aldermen has tried to pass the responsibility of medical transports from the city’s Corrections Department to their office.
“The sheriff has said openly in court many times [...] if there was financing to [get] the nine people assigned to a hospital unit, without undermining the ability to provide safety and security to the two court buildings and the juvenile court — that's fine,” Mason said. “The city should fund it instead of trying to force it down the throat of the sheriff who can not handle it because he doesn't have enough staff.”
A different future
After the hearing, Mason told reporters the issue over medical transports could be resolved if the city and Sheriff's Office could agree on funding positions.
One idea, the sheriff’s attorney said, could be to reallocate some vacant full-time employment positions from the City Justice Center to the Sheriff's Office.
Montgomery wants to take it one step further: taking over the city’s jail.
“I share your concerns regarding the adequacy of medical care provided to those in our custody,” he said in a written statement to STLPR following the hearing. “I propose that the Sheriff’s Office takes full responsibility for CJC operations.”
He said the shift would allow his department to directly oversee and improve medical services, a responsibility he says the Board of Aldermen already wants to place on him.
“The current CJC management structure has failed,” Montgomery said. “Detainee deaths, ongoing contraband problems, and inhumane conditions are public record [and] an open secret in our City.”
The sheriff contends that “direct management of the CJC would place accountability for the dignity of our justice system where there is now none.”
