Robert W. MacMeekin drove with his daughter on Saturday morning to seek a temporary protective order against her husband. By the early afternoon, police said the 74-year-old injury attorney was dead.

Mark Thomas Ryan was held at the Baltimore County Detention Center on Monday on charges of first-degree murder and use of a firearm, and Judge Lisa Ann Phelps ordered him to remain there without bond. The case moved through a fast and troubling sequence in which Alexandra Ryan said in court papers that her husband punched her in the head on Friday and warned he would “handle this a different way” before searching for the key to their gun safe.

In her petition early Saturday, Alexandra Ryan asked a judge to bar her husband from threatening or abusing her, from coming to their shared home in Bel Air or to her job, and from contacting her at all. She also sought custody of their two young sons and possession of the family dog, Eddie, a Pembroke Welsh corgi. The Harford County Sheriff’s Office said it did not serve Mark Ryan with a protective order.

According to the sheriff’s office, Alexandra Ryan arrived at the district court commissioner’s office at 8:32 a.m. Saturday. An interim protective order and an extreme risk protective order were granted at 9:28 a.m., then received by the sheriff’s office at 9:42 a.m. and by its Southern Precinct at 10:15 a.m. The agency said it first tried to serve the orders at 12:55 p.m. and tried again at 2:15 p.m., finding no one home.

Officers responded around 2:23 p.m. Saturday to the MacMeekin home in Baltimore County’s Phoenix neighborhood and found MacMeekin dead in the enclosed patio attached to the back of the house. Police said Alexandra Ryan told them she fled with the two children to her parents’ home, where they spent the night, while Mark Ryan kept contacting her through phone calls and text messages throughout the day.

The timeline leaves little room between the plea for help and the killing. Charging documents described MacMeekin’s effort to keep his daughter and her family safe as something that spiraled out of control within hours, and police said Alexandra Ryan and her mother were present and witnessed the shooting. On Monday, Ryan’s attorney said his client arrived at his in-laws’ home with a weapon. The unanswered question is not whether the paperwork existed or whether the orders were issued; it is how a man who had already been flagged as dangerous reached the point of killing the person who drove his daughter to court that same morning.