MILFORD — A 19-year-old Milford man was arrested and charged Tuesday after police investigation into three alleged robberies in April and May, one that left a man with a brain injury, authorities said.

Quentrae D. Carroll was charged with three counts of first-degree robbery, possession of a deadly weapon during the commission of a felony, first-degree assault, two counts of second-degree conspiracy, and third-degree assault.

Quentrae D. Carroll

He was sent to Sussex Correctional Institution in Georgetown on $85,000 cash bond.

According to the Milford Police Department, Mr. Carroll, a 17-year-old male and a third male, both not identified by authorities, allegedly threatened to shoot a 19-year-old male the afternoon of April 21 if he did not give up his property. Det. Young said the males allegedly referred to guns in their waistbands.

After the property was allegedly obtained near the parking lot of the Brightway Commons Apartment Complex, the males fled on foot, Milford Police alleged.

On the night of May 21, police alleged, Mr. Carroll, the same 17-year-old male and two other suspects not identified approached two males ages 29 and 52 in the 300 block of North Street and assaulted them.

According to police, the 52-year-old man was allegedly punched in the face several times and then struck with a glass bottle that knocked him unconscious. Property was then allegedly taken from his pockets, authorities said.

The 29-year-old man was also allegedly punched in the head and had his property taken, police said. His sneakers were taken off his feet, according to authorities.

The older man suffered a fractured skill, a brain bleed, and other serious facial and head injuries, police said. He was first taken to Bayhealth-Milford Memorial Hospital and then to Bayhealth-Kent General Hospital due to the severity of his injuries, according to authorities.

Police said a 17-year-old male was arrested and charged with first-degree robbery (three counts), possession of a deadly weapon during the commission of a felony, first-degree assault, second-degree conspiracy (two counts), and third-degree assault. He was held at the Stevenson House Detention Center in Dover on a secured bond, police said.

Police said the alleged incidents remain under investigaiton.