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ST. LOUIS — Missouri Attorney General Andrew Bailey filed suit Wednesday to remove city Sheriff Alfred Montgomery from office, saying the sheriff had hired a family member, broken the law on multiple occasions and failed to do his job properly.

The suit alleges Montgomery hired a half-brother, Malik Taylor, as a deputy. It says that Montgomery broke the law when he had a city jail official and a former sheriff’s deputy detained earlier this year, and when he failed to transport prisoners from the city jail for medical treatment.

And it says Montgomery misused public resources when he had a deputy pick up his kids and spent tens of thousands of dollars on golf carts, badges and a new SUV.

“Montgomery has abused his authority and resources repeatedly for his own personal benefit,” Bailey said at a news conference Wednesday announcing the suit. “This is about restoring the rule of law.”

Since taking office in January, Montgomery, 28, has run into a federal investigation, trouble with a budget deficit, and criticism from other elected officials. But Bailey’s suit is the most serious threat yet to his authority. Called a “quo warranto” petition, it challenges an elected official’s right to hold office, and has been used multiple times in years past to remove officials for crimes and misconduct.

Montgomery declined to comment on the suit when reached outside his office Wednesday afternoon. A spokesman, Jack Gieseke, pointedly disputed the nepotism allegation in a statement, saying Taylor is not related to Montgomery.

Two years ago, Bailey filed the same kind of suit against then-ӣ����Ƶ Circuit Attorney Kimberly M. Gardner. She resigned three months later under

growing pressure from the suit and the Legislature.

Quo warranto cases can be fairly straightforward in instances where officials have committed crimes, moved out of their jurisdictions or done something to become ineligible to continue in the job. Nepotism — hiring a relative — has historically been considered one of the most straightforward rationales for removing an elected official. The Missouri constitution says an official who does “shall thereby forfeit his office or employment.”

“That might be the whole case,” said Michael Wolff, a former Missouri Supreme Court justice.

Sharon Carpenter, the city’s former recorder of deeds, resigned in 2014 shortly after she was found to have hired a great-nephew.

ӣ����Ƶ County Councilman Dennis Hancock recently escaped removal after hiring his stepdaughter as his aide. But in making the deal to drop the charge, county Prosecuting Attorney Melissa Price Smith said the case against Hancock had problems, including the possibility that prosecutors may have violated rules about gathering evidence in the case.

Wednesday’s suit levels six individual counts against Montgomery, most of which elaborate on incidents already publicized in news reports.

• One not previously covered is the nepotism claim, which says that on his first full day in office, Montgomery hired Taylor as a sheriff’s deputy despite the fact that they share the same father. It also says that Montgomery has directed people to hide the fact that he and Taylor are related. The petition does not say exactly how the attorney general’s office verified the relation, but birth records for Montgomery and a Malik Taylor were requested from the city recorder’s office in recent weeks.

• The next claim concerns an episode in February, when Montgomery ordered the handcuffing and detention of the city’s deputy jail commissioner Montgomery said had impeded his access to a jail detainee he needed to talk to for an internal investigation. The petition says Montgomery had no right to do that, and therefore violated Ross’ civil rights by doing so. Neither Montgomery nor the handcuffing deputy were state-licensed peace officers. Unlike other sheriffs across the state, the ӣ����Ƶ sheriff is generally not permitted to enforce criminal laws.

• The petition says Montgomery had already committed a similar violation when he had a former deputy, Darryl Wilson, detained and disarmed when he was working as a private security guard in January. Montgomery accused Wilson of impersonating a sheriff’s deputy, but Wilson wasn’t, Bailey writes.

• Bailey also lists 59 times when the sheriff’s office failed to take jail inmates for medical treatment when required, a longtime duty of the sheriff. Montgomery has repeatedly argued that the trips are the responsibility of the city Corrections Division, which runs the jail. But Bailey said the law and precedent dating back decades prove otherwise, and make the failures a willful violation of the sheriff’s duty.

• The petition further states that Montgomery has illegally used public resources in multiple ways. For one thing, it says, he’s had an on-duty deputy picking up his children from school in a sheriff’s office car — despite prohibitions on officials getting personal benefits from their offices.

• Moreover, Bailey says, the tens of thousands of dollars spent on golf carts, badges and uniforms, a Chevrolet Tahoe and surveillance robots, among other things, were unnecessary and violated multiple statutes governing spending from special sheriff’s office funds.

The suit also features several asides.

For instance, early in his term, Montgomery installed a sign above his door with a new office motto: “Honesty. Integrity. Repsect.”

The sign included the typo, Bailey’s suit says.

Montgomery took several videos on TikTok of himself while driving on the highway, which is illegal, the suit argues.

And, last Friday, Montgomery went skydiving — even as his office was refusing to transport jail inmates to the hospital.

In a screenshot contained in the suit, Montgomery gives a thumbs up to the camera while a parachute deploys in the background.

The suit asks a judge to force Montgomery to immediately surrender his department-issue badge, weapon and vehicle, and forbid him from exercising any authority as an elected official, pending further proceedings.

State law tasks a “county commission” with appointing a new sheriff when the office is vacant.

In 1978, when ӣ����Ƶ Sheriff Benjamin L. Goins was removed via quo warranto following his conviction on federal racketeering and tax evasion charges, the Board of Aldermen appointed a temporary replacement. A special election was held later to pick a permanent sheriff.

Katie Kull of the Post-Dispatch contributed to this report.