Outside the Clyde S. Cahill Courthouse, one of Sheriff Alfred Montgomery’s attorneys, Justin Gelfand, told reporters, “This was a ‘charge first and investigate later’ case.”
Montgomery’s legal team pushed back on three days of allegations from the Missouri Attorney General’s Office, which argued he failed to do his job, abused his authority and mismanaged office finances — grounds, prosecutors say, for removing him from office.
Both sides delivered closing arguments Tuesday before Circuit Judge Steven R. Ohmer, who will decide whether Montgomery keeps the seat he won in 2020.
Montgomery, indicted by a federal grand jury in August for alleged witness intimidation, is being held in federal custody. He appeared in court wearing a light-blue-washed plaid suit and red tie, handcuffed at the waist. Invoking his Fifth Amendment right, he did not testify.
“Today was a very important day,” Gelfand said. “We think evidence came forth today that should have been part of the attorney general’s investigation and its case.”
Gun seizure incident
Prosecutors allege Montgomery illegally disarmed former sheriff’s deputy Darryl Wilson, who was working private security at a Phillips 66 gas station in January. “This case does not meet sufficiency of proof,” said former Judge David Mason, another defense attorney.
The defense acknowledged Montgomery confronted Wilson and took his weapon but argued the sheriff acted properly because Wilson — wearing tan pants and a black shirt resembling a sheriff’s uniform — misled the public after resigning. The gas station owner testified he hired Wilson believing he was still a deputy, after calling the sheriff’s office the previous year seeking off-duty help.
Body-camera footage showed a police lieutenant telling Montgomery he had no authority to take the gun. Gelfand countered that it is the Legislature, not police, that defines a sheriff’s powers and that lawmakers gave sheriffs responsibility over matters involving deputies, including secondary employment.
Handcuffing allegation
Montgomery’s defense also addressed allegations that he illegally ordered the handcuffing of acting deputy jail chief Tammy Ross after she refused his request to access a detainee connected to a sexual assault investigation.
The defense relied on testimony from former Master Sgt. Bryan Robins, who said he handcuffed Ross and did not recall Montgomery giving any such order. A subsequent police investigation led to the firing of the sheriff’s employee accused in the sexual assault case.
Financial accusations and jail custody
Defense lawyers rejected prosecutors’ claims of financial mismanagement, saying any concerns were “an accounting discrepancy” and that Montgomery had legal authority over spending.
Prosecutors closed by arguing Montgomery cannot serve while jailed. “Being sheriff is not a remote position — it’s a full time, in-person job, and Alfred Montgomery can’t do it from a jail cell in Illinois,” said Assistant Attorney General Greg Goodwin.
Mason urged the judge not to let federal detention determine the outcome, arguing Magistrate Judge John Bodenhausen had effectively “usurped” Ohmer’s authority by jailing Montgomery.
Broader context
The case was brought under former Attorney General Andrew Bailey using the same quo warranto process he pursued in his unsuccessful effort to remove St. Louis Circuit Attorney Kim Gardner. Historically, the process has been used against Missouri sheriffs only after a conviction.
“What a quo warranto ultimately does is it literally overturns the results of a free and fair election,” Gelfand said. “There’s nothing that happened in this courtroom that we believe warrants that writ.”
With arguments complete, Montgomery’s future now rests with Ohmer.
Sylvester Brown Jr. is the Deaconess Foundation Community Advocacy Fellow.