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.

For more info, visit CNN.com