(CNN) — By the time then-sheriff’s Deputy Sean Grayson gunned down a 36-year-old mother in her home, fellow law enforcement officers and residents in the Illinois communities he served had already raised a host of concerns about him.
Grayson, 30, is now charged with murder in the July 6 death of Sonya Massey; he has pleaded not guilty. Massey, a mother of two, joined Breonna Taylor and Atatiana Jefferson on a list of Black women killed in their own homes by law enforcement – whose deadly use of force came under scrutiny.
“Sonya Massey lost her life due to an unjustifiable and reckless decision by former Deputy Sean Grayson,” the Sangamon County sheriff said in a statement after firing Grayson.
Now, more details are emerging about Grayson’s alleged misconduct prior to killing Massey. An attorney representing Grayson, Daniel Fultz, declined to comment to CNN for this story.
Here’s a timeline of some of Grayson’s issues with the law, the military and his work in policing – which spanned six agencies in four years.
August 2015: DUI guilty plea
While enlisted in the US Army as an auto mechanic, Grayson pleaded guilty to DUI in August 2015 in Macoupin County, Illinois – between Springfield and St. Louis – court records show. He paid more than $1,320 in fines.
February 2016: Army discharge
Grayson received a general discharge under honorable conditions from the Army in 2016 due to “misconduct (serious offense),” according to a Department of Defense document included in Grayson’s Sangamon County personnel file.
“The ‘serious misconduct’ listed in his discharge, as I understood from a letter provided by a commanding officer, was his first DUI,” the Sangamon County sheriff said in series of statements in late July.
“We were aware of the DUI at the time of hire,” Sheriff Jack Campbell said. “Past DUI convictions are not disqualifying criteria for a deputy. We recognize that individuals can change and improve over time.”
Grayson never deployed while in the Army and left in the rank of private first class, his discharge certificate states. The file also listed several of Grayson’s awards, including the National Defense Service Medal and the Global War on Terrorism Service Medal.
July 2016: Another DUI guilty plea
Grayson was charged again with DUI, also in Macoupin County. He pleaded guilty and paid more than $2,400 in fines, court records show.
August 2020 to July 2021: Part-time police job
Grayson worked as a part-time police officer in Pawnee, population 2,700, according to his records from the Illinois Law Enforcement Training and Standards Board.
He left because he was “looking for full-time” work, Grayson wrote in a future job application.
June 2021: State certification
Grayson received state certification to work as a part-time law enforcement officer, according to the Illinois Law Enforcement Training and Standards Board. He went to a “part time law enforcement academy,” a future job application said.
February 2021 to May 2021: 2nd part-time police job
While he was working part-time for Pawnee police, Grayson also worked part-time as a police officer in Kincaid, an Illinois village of about 1,350 people.
He left because he wanted “to be a Sangamon County sheriff deputy,” Grayson wrote in his application for the deputy post.
May 2021 to December 2021: 3rd part-time police job
Grayson worked part-time at the nearby Virden Police Department, according to the state records.
There, he “was proactive and worked well with the public,” Virden’s police chief later said, according to a Sangamon County lieutenant’s summary of the chief’s comments. The lieutenant contacted Virden’s police chief during a background check for Grayson’s job application.
“Grayson did not demonstrate good officer safety skills however,” the lieutenant wrote, adding the chief “advised me he believes that was because he was new to the job.”
In his response to Wisehart’s complaint, Grayson acknowledged he visited Wisehart in jail to ask “if he knew a male that was connected to Chelsey Lowe and George Wisehart,” Grayson wrote in a memo to a Logan County chief deputy.
Grayson said he did not make any unprofessional comments to Wisehart.
“I did not harass George. I have not interviewed or spoken to George alone,” Grayson wrote. “I did not have knowledge of the amount Chelsey bonded out on. I did not have a conversation with George about Chelsey having relationships with other males.”
Just like with Lowe’s complaint, Wisehart’s complaint was deemed “unfounded,” with “trained on best practice” written in the file. Wisehart is serving a 10-year state prison sentence.
July 2021 to May 2022: Full-time police work
Grayson worked full-time at the Auburn Police Department, the state records show. CNN’s review of Grayson’s records did not reveal any problems or disciplinary issues during his time in Auburn, Illinois.
May 2022: First sheriff’s office position
Grayson was hired by the Logan County Sheriff’s Office, northeast of Springfield, records show.
September 12, 2022: Criticism over vehicle pursuit
Grayson failed to adequately slow down after his supervisor called off a vehicle pursuit, according to his Logan County personnel files. Grayson, a probationary deputy at the time, then struck a deer.
“Deputy Grayson pursued the truck through Lincoln at a high rate of speed, reaching speeds of 63/30 MPH zone and, in my opinion, failed to show due caution while driving through stop intersections,” Chief Deputy Nathan Miller wrote in a report.
Grayson’s supervisor “terminated the pursuit,” and Grayson turned off his emergency lights, the report said. But Grayson “continued at a high rate of speed (110/55 mph zone) prior to striking the deer.”
May 2023: New sheriff’s office job
Grayson left Logan County to become a Sangamon County sheriff’s deputy. A background check was performed before Grayson was hired, the Sangamon County sheriff said.
“No other law enforcement agency reported problems with Grayson before we hired him,” Campbell later said. In addition, “Grayson’s personnel file includes references from people I know well.”
In his Sangamon County job application, Grayson wrote: “My communication, People-centric nature, and compassion have afforded me excellent critical thinking skills.”
May 2024: Complaint over attempted home search
A man filed a complaint about Grayson with the Sangamon County Sheriff’s Office. The man said he and a 17-year-old girl were questioned at a home around 11:30 p.m. on May 1 by officers from multiple agencies about the whereabouts of another person.
After officers demanded to be let in the house, the complaint said, Grayson accused the girl of obstructing an investigation and “then threatened her that if she didn’t let them in the house, he was going to put her in cuffs and she would go to jail.”
“I believe it is 100% unlawful to threaten detainment and being arrested of (sic) not letting officers into the home with no warrant,” the complainant wrote. “More specifically, verbally attacking a 17 year old girl and failing to contact adults, supervisors, or parents of any kind.”
The Sangamon County Sheriff’s Office declined to investigate beyond an informal inquiry, noting the complainant did not meet with a lieutenant. “After reviewing Deputy Grayson’s BWC (body-worn camera), it was determined that his actions were warranted given the serious nature of the call,” a chief deputy wrote. “Therefore, no formal investigation was conducted.”
There was no response to the incident from Grayson in his personnel file, and it’s not clear whether Grayson was asked about the complaint before the inquiry was closed. Fultz, an attorney for Grayson, has declined to comment to CNN on Grayson’s personnel records.
July 6, 2024: The killing of Sonya Massey
Grayson and another deputy responded to Massey’s home after a report of a possible prowler. Bodycam footage from the other deputy initially showed a calm encounter between the mother and the two deputies.
When the deputies were inside the home speaking with Massey, they noted a pot of boiling water on the lit stove. Massey got up and went to the kitchen to turn off the heat and take the pot off the stove.
“We don’t need a fire while we’re here,” Grayson said.
When Massey picked up the pot, she noticed a deputy retreat.
“Where are you going?” Massey asked.
“Away from your hot, steaming water,” the deputy responded.
“Oh, I rebuke you in the name of Jesus,” Massey said.
“Huh?” the deputy responded.
“I rebuke you in the name of Jesus,” Massey repeated.
“You better f**king not,” Grayson replied, “or I swear to God I’ll f**king shoot you in the f**king face.”
Grayson then drew his gun and pointed it at Massey, who looked frightened.
“OK, I’m sorry,” Massey said as she ducked under the kitchen counter.
“Drop the f**king pot!” both deputies yelled. Then three shots rang out.
After Massey was mortally wounded, the other deputy said he was going to get a medical kit to help. Grayson replied: “Nah, it’s a headshot, dude. She’s done. You can go get it, but that’s a headshot.”
Later, Grayson spoke to a group of law enforcement officers outside. “Yeah, I’m good,” he said on the bodycam footage. “This f**king b*tch is crazy.”
July 17, 2024: Fired and charged
A Sangamon County grand jury indicted Grayson in Massey’s killing on three counts of first-degree murder, one count of aggravated battery with a firearm and one count of official misconduct on July 17, said John Milhiser, the state’s attorney for Sangamon County.
That same day, the Sangamon County sheriff announced Grayson was fired.
Grayson pleaded not guilty at his arraignment and was denied pretrial release, according to court records. A pretrial hearing is scheduled for October 21.
Massey’s 17-year-old son, Malachi, has told CNN he wants Grayson locked up behind bars for as long as possible.
“He had no regard for my mom,” Malachi said. “So we need to have no regard for him.”
