Sean Grayson had enough infractions in his military and police force records to raise red flags. Still, he got and kept his badge under multiple departments. Now, Sonya Massey, a 36-year-old Black woman believed to be experiencing mental health experiences, is dead.

The former Illinois deputy fatally shot Massey in the face inside her home after she called 911 on July 6. While her family grieves, Grayson is in jail awaiting trial for first-degree murder, aggravated battery with a firearm, and official misconduct. Grayson, who is white, has pleaded not guilty.

RELATED: Sheriff Of Illinois Deputy Who Shot Sonya Massey Breaks Silence

Here’s a breakdown of the red flags experts say his employers should’ve waved.

 Sean P. Grayson Busted For DUI Twice In One Year

According to the Associated Press, Grayson got the Army’s boot for the first of two drunken driving convictions in which he had a weapon in his car. Before becoming a cop, he was convicted twice within a year of driving under the influence.

Grayson enlisted in the Army in 2014. Prosecutors charged him with DUI in Macoupin County, just south of Sangamon County, after traffic stops on Aug. 10, 2015, and again on July 26, 2016.

The first DUI led to his discharge from the military in February 2016 for “serious misconduct,” according to a U.S. official who spoke to AP News on condition of anonymity to discuss personnel information. The source added that Grayson had an unregistered gun in his vehicle. Grayson did not face a weapons charge because he was a resident of Fort Riley, Kansas. Kansas has an open-carry firearms law.

Grayson received a general discharge under honorable conditions rather than an honorable discharge because he was charged by a civilian law enforcement agency, and his military service was otherwise good.

Sean Smoot, chairman of the Illinois Law Enforcement Training and Standards Board, said that a misdemeanor DUI charge doesn’t by law preclude someone from serving in law enforcement. However, a hiring agency can certainly consider it.

“Some police departments would not have hired someone with one DUI,” Smoot said. “I am shocked an agency would hire someone with two DUIs, but multiple agencies apparently did.”

Sean Grayson’s former Sheriff Jack Campbell of Sangamon County said Grayson got the approval stamp from the county merit commission and state law enforcement board. DUIs aside, he passed a drug test, criminal background check, psychological evaluation, and 16-week academy course.

His Former Agency Said He Needed More Training In “High-Stress Decision-Making” 

Before he came to his last policing job at Springfield, Grayson worked for a year as a deputy sheriff in Logan County, just to the northeast. According to a report obtained under a public records request, in November 2022, he was told he needed more training, including “high-stress decision-making classes.” At the time, he failed to follow an order to halt a high-speed pursuit, reaching speeds of 110 mph (177 kph) before colliding with a deer.

Sean Grayson Had Misconduct Complaints At Logan County Office

The Logan County records also include complaints of misconduct from two people Grayson arrested. A woman reported Grayson after he gave her a glove and told her to remove the contraband in front of him and another male officer. She had admitted to having drugs in a body cavity.

She later was taken to a hospital to have it removed and claimed Grayson burst through the curtain during the procedure. He denied both complaints and resigned from Logan County before the investigation was complete.

Another Agency Had Concerns About His “Bragging”

To be clear, Sean Grayson has had six policing jobs in four years. An employment report from his former agency, Auburn, south of Springfield, praises his wins. Grayson was reportedly always early for work, eager for training, receptive to criticism, and had not faced disciplinary action.

However, he struggled with report writing, was “not great with evidence — left items lying around the office,” and was “a bragger.”

Sonya Massey & Her Mother’s 911 Calls On The Day She Died

Sonya Massey died in her home about 200 miles south of Chicago after deputies responded to her 911 call about a possible prowler early on July 6.

Prosecutors alleged that after Grayson allowed Massey to move a pot of water heating on the stove and she set it on a counter, Grayson then “aggressively yelled” at Massey over the pot and pulled his 9 mm pistol.

Massey then put her hands in the air, said, “I’m sorry,” and ducked for cover. But  Grayson still managed to shoot her in the face. The officer also discouraged the other deputy from getting his medical kit.

Most recently, the phone calls Sonya and her mother made to 911 on the day of her death were released.

RELATED: Details Are Revealed About The Calls Sonya Massey & Her Mom Made To Illinois Police In The Hours Before Her Death (LISTEN)

Associated Press staff John O’Connor, Lolita Baldor, Melissa Perez Winder, and Ed White contributed to this report.