A Denison man accused of shooting his friend in the face outside a bar in 2017 pleaded guilty to manslaughter on Monday.

Brandon Jeffery is scheduled for sentencing in January and faces a maximum possible sentence of 20 years in prison for his role in the death of Devin Wayne Owens outside Tupelo Honey in Denison last year.

A message seeking comment could not be left for the Grayson County District Attorney’s Office Monday evening and calls placed to Jeffery’s attorney, Joe N. Smith, were not immediately returned. Jeffery, 26, was charged with murder after he allegedly shot Owens as the two sat in a parked car outside Tupelo Honey on May 5, 2017.

Owens was taken to a local hospital where he later died. Jeffery fled the scene after the shooting, witnesses said, but later told investigators he had been playing with the handgun and thought it was unloaded when the firearm went off.