Even in the weird and wild world of ѿý politics, Alfred Montgomery is an overachiever.
The new city sheriff has somehow managed to rise above — or sink below, as the case may be — the recent run of missteps and improprieties of city government and the public school system.
Indeed, the man is on a roll.
Before we get to the most recent flap involving Montgomery — one in which a deputy says the sheriff made him roll dice to save his job — let’s look at the first two months of Montgomery’s term.
Montgomery put himself in line for the job when he won the Democratic primary in August against incumbent Vernon Betts. The race was close enough to warrant a recount: Montgomery beat Betts by 221 votes, out of about 45,000 cast.
Montgomery’s victory followed months of sharply worded barbs. Betts noted Montgomery worked as a deputy for several months but was fired by Betts for absenteeism, insubordination and substandard work.
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Montgomery also claimed that he had a bachelor’s degree from Arizona State University. Problem is, the ASU registrar’s office couldn’t find any record of Montgomery’s attendance.
Let’s note here that the need for an elected sheriff has been called into question for years.
In ѿý, the sheriff’s department’s main job is providing courthouse security, transporting prisoners and serving legal papers. It does not run the jail, nor does it perform general law enforcement.
Some have wondered why the city needs an elected position that seems to serve as little more than a political patronage waystation where one party loyalist gets a job with a nice paycheck and a badge in exchange for getting other party faithful jobs with decent paychecks and badges.
In 2010, Missouri Auditor Susan Montee said the sheriff and other elected offices “hobbled” the city.
“You have a whole lot of people around that are running their own separate shop,” she said.
And Montgomery didn’t even wait to officially take office before he put his hands all over the shop.
A month before he was sworn in, Montgomery gave letters to Betts’ top officers, telling them they were to be let go Jan. 1, the day he became sheriff.
Then, just three weeks into his term, Montgomery threatened to arrest a former deputy while he worked a security job at a gas station and was also going to confiscate his personal handgun, .
The former deputy called city police, and the flap concluded with the man getting to keep his gun and his security gig, the station said.
Two weeks ago, a tempest stirred out of an allegation that a female detainee of the ѿý jail had been having sexual relations for several weeks with a deputy.
So on Feb. 14, Montgomery marched the long city block to the jail and demanded to interview the detainee. Deputy Corrections Commissioner Tammy Ross blocked his access.
Seems Montgomery’s raid on the jail might have stood on shaky legal ground. But undaunted by questions of legality, Montgomery opted for another solution: He handcuffed Ross and detained her.
Making his case to local media, Montgomery said he had permission from the city’s Department of Public Safety and the police to interview the detainee.
The rebuttals to Montgomery’s claims came hard and fast.
Charles Coyle, city public safety director, said Montgomery “lied, repeatedly.”
“At no time and under no circumstance did I give a directive to allow Sheriff Montgomery or his staff to interview a detainee,” Coyle said.
A police spokesman said, “There was an order given by this department not to interview the victim of a crime that we were investigating.”
Now, federal authorities are investigating Montgomery after Mayor Tishaura O. Jones called the FBI about the incident.
Jones, who endorsed Montgomery for the office, later described Montgomery’s actions as “just wrong on I don’t know how many levels.”
All of that brings us to the latest attraction to pop out of a sheriff’s car: The Golden Dice.
Not only do we have games of chance in this story that surfaced recently, we also have allegations of political machinations.
It started in January, when Alderwoman Anne Schweitzer complained to Montgomery that deputy Tony Kirchner had been campaigning for alderman while in his uniform, a violation of state law.

Tony Kirchner, left, and Anne Schweitzer
Kirchner lost to Schweitzer two years ago and opposes her again in April.
Schweitzer sent photos to Montgomery that showed Kirchner at community meetings wearing various parts of his uniform. She said in an interview that a uniformed Kirchner has been a common sight at ward meetings.
“A political axe job,” Kirchner’s attorneys called it.
When asked to respond to the contention that her actions were politically motivated, Schweitzer said, “If you want to be the alderman, you should follow the rules.”
As to the dice-rolling incident, Kirchner said Montgomery then called him into the office on Jan. 22 and told him that because of Schweitzer’s allegations, he was going to lose his job — unless he could roll a “seven” with a pair of gold dice Montgomery keeps in his desk drawer.
In a story first reported last week by , Montgomery denied the dice roll. But Kirchner has provided local media with a 45-minute audio recording he made of his meeting with Montgomery.
During the conversation, Kirchner denied Schweitzer’s allegations and said he wanted to take vacation and family leave time, due to his father’s death, to figure out how to proceed.
Montgomery, however, insisted on the dice roll, saying it was the best chance Kirchner would get: two rolls to get a seven.
If Kirchner was successful, “we’ll go with whatever you want,” Montgomery said.
Kirchner protested and said the dice roll made him feel like he was being “put on the spot.” He again asked for leave time.
Montgomery then told Kirchner, “This is as fair as it gets.”
Kirchner eventually played along; on his second attempt, he rolled a seven.
At that point, Montgomery said to a third party in the office, “Give (Kirchner) whatever leave time he needs, and we’ll go from there.”
Kirchner’s attorneys say their client was authorized for 12 weeks of leave, as well as about six weeks of vacation and compensatory time available.
But on Feb. 4, less than two weeks after the dice roll, Kirchner could not get a prescription filled because his health insurance had been stopped.
Kirchner’s attorneys said their client eventually learned that city records indicated he had resigned on Jan. 26, just four days after winning the dice roll.
Montgomery has been unavailable to comment. He could not be reached on his cellphone, and he did not return messages left at the sheriff’s office.
But in a statement released Saturday, Montgomery defended his actions, saying they were dictated by “the complex realm of leadership.”
The statement notes that because Kirchner seemed to be in “a state of emotional distress” and was armed, Montgomery “deployed a creative de-escalation strategy to ease the tension and provide him with a sense of control.”
If Montgomery was betting on that statement to settle things down, he shot craps.
On Monday, Kirchner filed a defamation suit against Montgomery for the statement’s claims that Kirchner was emotionally unstable and even possibly dangerous.
“Montgomery is embarrassed, and he should be. But rather than apologizing for lying to the public ... he instead decided to defame my client,” said Brandy Barth, one of Kirchner’s lawyers.
“Reprehensible,” is how Kirchner’s other lawyer, Talmage Newton IV, has described the situation.
Even Schweitzer labeled the incident as “unprofessional.”
Kirchner’s attorneys said they also will file an employment discrimination suit, so how this tale ends remains to be seen.
But one thing is clear: Alfred Montgomery doesn’t honor his bets.
Post-Dispatch photographers capture hundreds of images each week; here's a glimpse at the week of Feb. 16, 2025. Video edited by Jenna Jones.