When Alfred Montgomery took office as St. Louis sheriff six months ago, some saw him as a symbol of a new era of leadership. But his tenure quickly became embroiled with controversy.
Montgomery, who is 28 and has described himself as the nation’s youngest sheriff, is facing a range of allegations, including personnel issues, defamation, civil rights violations, misuse of public funds and nepotism. Media outlets have reported the allegations, and his critics have trumpeted them. His claims about his educational and professional endeavors have been murky and misleading, according to reporting from the St. Louis Post-Dispatch.
In response to the turmoil in the sheriff’s office, Missouri Attorney General Andrew Bailey, a Republican, called on Montgomery to immediately resign or face a quo warranto — a rarely used legal action that challenges an elected official’s right to hold public office. Montgomery refused to step down, and Bailey filed the motion last Wednesday. He used the same tactic in 2023 to force former Circuit Attorney Kim Gardner’s eventual resignation.
Bailey wasn’t the first to call for Montgomery’s resignation. The Holy Joe Society, a nonprofit legal group, called for Montgomery to resign or be removed earlier this year. St. Louis Mayor Cara Spencer also said she’s lost confidence in the sheriff’s ability to lead his department.
Still, the Democratic sheriff remains defiant, saying he has done nothing illegal and intends to serve out the remainder of his term.
“Let me be very clear, very clear that I will not resign,” Montgomery said during a press conference late last month. “I was elected by the people of St. Louis to serve as their sheriff, and I intend to honor that commitment.”
Montgomery’s quo warranto proceedings are set to begin at 11 a.m. Wednesday in the Mel Carnahan Courthouse. He’ll be represented by a slate of attorneys, including employment attorney Matt Ghio, former federal prosecutor Justin Gelfand and retired Circuit Judge David C. Mason.
The Missouri Supreme Court appointed recently retired St. Louis County Circuit Judge Steven R. Ohmer to oversee the case after all the judges in Missouri’s 22nd Judicial Circuit recused themselves from the case.
Bailey is making six charges against Montgomery. Here’s what we know about the 87-page legal filing.
Count 1: Nepotism
Bailey argues Montgomery broke the state’s anti-nepotism clause when his office hired his half brother as a deputy sheriff. According to the writ, Malik Taylor was hired in January as a probationary deputy sheriff and now serves as a senior deputy.
The brief claims Taylor and Montgomery are related through their father, but the sheriff has denied any familial relationship between the two and insists the tie is based on rumors. Bailey’s office said that it has birth certificates proving the relationship and that Montgomery has tried to hide his relationship with Taylor.
Missouri’s constitution prohibits elected officials from hiring family members.
“Any public officer or employee in this state who by virtue of his office or employment names or appoints to public office or employment any relative within the fourth degree, by consanguinity or affinity, shall thereby forfeit his office or employment,” according to Article 7, Section 6 of the Missouri Constitution.
The state’s anti-nepotism clause has made headlines over the years. Former St. Louis County Prosecuting Attorney Wesley Bell filed a quo warranto against Councilman Dennis Hancock last year for hiring his stepdaughter as his assistant. Bell's successor, Melissa Price-Smith, has dropped the case.
Count 2: ‘Kidnapping’ Tammy Ross
The most serious allegations against Montgomery center on the handcuffing of the City Justice Center’s Deputy Jail Commissioner Tammy Ross last February.
Montgomery previously claimed he had Ross handcuffed after she blocked him from interviewing a detainee who had accused a sheriff's deputy of sexual assault, who was later arrested. Montgomery said at the time that former Public Safety Director Charles Coyle had granted access to his internal investigator but abruptly revoked permission. Montgomery justified detaining Ross by saying she was impeding the sheriff's duties.
According to a police spokesperson, the St. Louis Metropolitan Police Department referred the incident to the Federal Bureau of Investigation. The FBI, by policy, neither confirms nor denies ongoing investigations.
In the quo warranto petition, Bailey alleges the sheriff’s true motive was to provoke a confrontation inside the jail. The suit says Montgomery dispatched two deputies under the pretense of serving a “time-sensitive” order of protection but contends the order wasn’t urgent. Instead, Bailey argues, this was a ploy to get Montgomery inside the jail amid ongoing tensions with Ross, who he said had locked him out of his portion of the facility for weeks.
Security camera footage, cited in the filing, shows Montgomery confronting Ross alongside two deputies. The attorney general quotes Montgomery telling one of them to “handcuff her.” Bailey alleges that both Montgomery and the deputy who applied the handcuffs were not licensed peace officers. Ross was eventually released, shortly after another deputy was seen whispering in Montgomery’s ear.
The core of Bailey’s argument is that Montgomery unlawfully detained Ross, violating her constitutional rights and exceeding his legal authority as sheriff. The suit alleges that SLMPD officers did not authorize Montgomery to interview the detainee, contradicting the sheriff’s claims.
According to Bailey’s filing, Coyle said that Montgomery “lied repeatedly” and that he “at no time and under no circumstances” permitted Montgomery to interview a detainee.
Coyle said the same thing in a statement in February: “At no time and under no circumstance did I give a directive to allow Sheriff Montgomery or his staff to interview a detainee within the custody of the Corrections Division. Allegations surrounding sexual crimes are incredibly sensitive and should only be handled by individuals authorized to conduct high-level criminal investigations.”
Bailey also accuses Montgomery of fabricating the story with the help of subordinates, including drafting after-the-fact incident reports to justify Ross’ arrest by alleging she interfered with the earlier service of the order of protection.
The petition contends that handcuffing Ross constituted an arrest and was an unconstitutional, warrantless seizure that amounts to felony kidnapping. Ross has sued Montgomery in his professional and personal capacity over the incident.
“When an arrest is made, '[t]he officer must inform the defendant by what authority he acts . . .' § 544.180. 175. But, on information and belief, neither Respondent nor his deputies informed Deputy Commissioner Ross by what authority he or they acted in arresting her,” the writ reads.
Count 3: Disarming Darryl Wilson
The writ alleges Montgomery, once again, overstepped his authority — this time by attempting to "enforce the general criminal laws of the state" when he and a subordinate detained former deputy sheriff Darryl Wilson and confiscated his personal firearm while Wilson was working a private security job at a south St. Louis gas station last January.
Months later, Wilson attempted to obtain a restraining order against Montgomery. According to a transcript from an April order of protection hearing in St. Louis County obtained by STLPR, Wilson testified he was leaning against the counter at the Kaiser Grand Mart when Montgomery and Capt. Anthony Anderson confronted him, detained him and said they were taking his weapon.
Anderson — who was then overseeing secondary employment at the sheriff’s office but has since retired — testified he had received a tip Wilson was working security earlier that day and went to check whether he was in full uniform, as required by department policy.
Wilson said he called police after the encounter. But both Montgomery and Anderson testified it was actually the sheriff who called 911, reporting that a man was “impersonating a sheriff’s deputy” while working security.
Anderson said Montgomery asked Wilson to disarm. Wilson declined but ultimately handed the captain his firearm voluntarily.
Wilson said his gun was returned once city police arrived and that Anderson later apologized for the incident. “When Tony Anderson brought my weapon back, you know, we pulled off to the side and his specific words was: ‘Mr. Wilson, I am sorry. You know, we took your weapon,’” he testified, stating Anderson added: “Alfred Montgomery is my boss. I have to do what he tells me to do.”
Anderson denied the claims in court and allegedly told Wilson that if he’s going to work a security position slated for a deputy sheriff and wear a weapon, then he has to be in full uniform.
The attorney general’s filing notes that SLMPD officers responding to the call observed Wilson wasn’t wearing any clothing suggesting he was impersonating law enforcement. However, court records show neither Gateway Security Services — which issued his security license — nor the gas station itself were aware Wilson was no longer employed by the sheriff’s office at the time.
There’s a significant pay gap between a licensed security officer and a sworn deputy, according to court records, roughly $22 vs. $55 per hour.
SLMPD also referred this interaction to the FBI, a police spokesperson previously told STLPR.
In the April hearing, Montgomery testified Wilson had been under investigation for an allegation of sexual harassment when he resigned from the department. Wilson says he signed a resignation letter without knowing what the document contained.
After leaving office, Montgomery said Wilson returned to the courthouse on multiple occasions and engaged in roughhousing while wearing clothing similar to the city sheriff’s deputy uniform. When the sheriff brought his concerns to Wilson’s new supervisor at the St. Louis County Sheriff’s Office, Wilson said it was part of a larger pattern of harassment by Montgomery. A judge subsequently denied Wilson’s request for a protective order.
Bailey alleges that the January incident amounts to misdemeanor kidnapping, unlawful seizure of a firearm and violations of the Missouri Constitution as well as the Second and Fourth Amendments of the U.S. Constitution.
Count 4: Refusing to transport and supervise hospitalized detainees
St. Louis officials have criticized Montgomery and the Sheriff’s Department for threatening to stop transporting detainees from the city jail to area hospitals.
Bailey alleges that Montgomery failed to transport 59 inmates for medical treatment between January and June — despite a longstanding precedent by previous sheriffs to do so.
The attorney general based the claim around a 1999 agreement from the late Sheriff Jim Murphy and a 2004 memorandum from the city counselor’s office opining that “it is the Sheriff’s responsibility to guard a prisoner, including a prisoner in a hospital, and that this responsibility to ‘guard’ also implies that the Sheriff has the duty to transport.”
The writ alleges Montgomery went skydiving on June 20 — hours after failing to transport a detainee — but the video the attorney general referenced showing the plunge appears to have been posted two days later when the sheriff was off work.
In a letter to former Mayor Tishaura Jones, Montgomery argued that transporting detainees to the hospital wasn’t his department’s responsibility — but rather that of the City Justice Center, citing its contract with the jail’s medical provider. He asked the city for more resources to carry out that request, as had his predecessors at various times, according to documents obtained by STLPR.
The threat drew the ire of the St. Louis Board of Aldermen’s budget committee after Montgomery requested additional funding for the sheriff’s “hospital unit” and blamed the office’s overtime costs for contributing to a roughly $635,000 departmental shortfall.
A sheriff’s office spokesperson previously told STLPR that the unit was on the chopping block due to budget constraints, saying the department needed to cut costs to meet its core statutory duties: securing courtrooms for the 22nd Judicial Circuit, transporting detainees to and from court and serving eviction notices and legal documents. Montgomery later said he never intended to stop transporting sick detainees to the hospital.
The hospital transport job was typically handled by former Sheriff Vernon Betts, but it’s not a duty the department is legally required to perform, according to Mason, a sheriff’s attorney, during a June press conference.
Since then, 5th Ward Alderman Matt Devoti filed legislation clarifying what the sheriff’s role entails — including transporting detainees to the hospital. A court has yet to decide if it is a sheriff’s legal duty to transport detainees to the hospital.
Bailey contends Montgomery has failed to uphold one of his fundamental duties as sheriff, according to the writ, and has “placed an onerous burden on other departments and has threatened the safety of the City of St. Louis.”
Count 5: Misuse of public resources
Bailey claims the sheriff personally benefited from misusing public resources, including by having an employee chauffeur his children to and from school on multiple occasions.
“By using a deputy and an office vehicle to transport his children, [Montgomery] has used governmental resources and taxpayer money to obtain an improper, personal financial gain,” the writ reads. “When he needed childcare services, Respondent turned to a deputy who is getting paid through taxpayer money, instead of relying on acceptable means to complete that work, which included the transporting and supervision of his children after school.”
Bailey’s filing goes on to call Montgomery a “usurper who must be removed.”
Count 6: Financial mismanagement
Bailey’s final count against Montgomery is the allegation that he’s “willfully or fraudulently violated an official duty by mismanaging the finances and creating an increasing monetary deficit for [the St. Louis Sheriff’s] office.”
The writ alleges that the sheriff has squandered tens of thousands of taxpayer dollars on questionable purchases, such as golf carts, gold‑plated badges, a take‑home Chevy Tahoe and even “office robots.”
The sheriff has attempted to justify the purchases, citing a fleet of old and damaged vehicles and the need for cameras in the courtrooms. Mason, the sheriff’s attorney, told reporters that the department purchased the surveillance robots to increase courtroom security but insisted that taxpayer funds weren’t used. He said the funds were pulled from a pot of fees collected from serving legal papers and other revenue streams.
A sheriff’s department spokesperson said new badges were necessary because previous administrations had given them out to individuals not affiliated with the department.
Bailey further contends that Montgomery is paying more than $15,000 in attorney fees by employing Mason and Blake Lawrence, who serves as “general counsel” for the office. Missouri law allows for the hiring of one attorney to aid and advise the sheriff.
Finally, Bailey points to the sheriff’s “unpredicted payouts.”
Before taking office, Montgomery said he planned to fire Betts’ top brass — going so far as to send them letters ahead of time to avoid catching anyone off guard during the holidays.
“We have to move this office forward,” Montgomery said at the time. “We can't risk the threats that we're getting from the current administration as far as destroying property or services … before I come into the office.”
Montgomery fired about 17 longtime employees — triggering roughly $500,000 in payouts for accrued benefits. His office contends the nearly $635,000 deficit was largely inherited from Betts’ administration.
Documents obtained by STLPR show Montgomery’s team alleges Betts authorized a final payroll just days before leaving office, including more than a quarter-million dollars in comp time to outgoing administrators. The claim has not independently been verified by St. Louis Public Radio. Betts said the payouts were staff members’ earned benefits that they were entitled to when they left the office and that he didn’t provide kickbacks.
“Respondent has knowingly and willfully wasted, and continues to waste, taxpayer money by making unnecessary purchases and expenditures,” the writ reads. “[Montgomery] committed willful or fraudulent violation of his official duties by mismanaging the department’s budget through unnecessary spending and by misrepresenting facts to the Board of Aldermen.”
What's next?
Bailey is calling for the removal of Montgomery and the immediate forfeiture of his badge, service weapon, department vehicle and all other county property.
In court filings, Bailey points out that the city lacks a coroner — a role that would typically step in place of an absent sheriff — and urges the court to authorize the St. Louis Metropolitan Police Department to temporarily assume those duties. He’s also requesting that the city appoint a contact person to oversee the office until the appropriate executive names a replacement.
The attorney general is also seeking court costs and any additional relief that the court deems appropriate, setting the stage for a rare legal showdown.
If Bailey were to prevail, Betts said he would hope the governor would consider him to fill his old post.
"I'll never run for political office in St. Louis again, but I will take an appointment if the governor … has enough confidence in me,” he said on Tuesday afternoon. “I am willing to go back and clean the place up.”
