SPRINGFIELD (AP) – A former Missouri school superintendent has pleaded not guilty to killing a Springfield couple from whom police said he had requested a large loan.

KOLR-TV reports 53-year-old Mark Porter appeared in court Monday on two counts of first-degree murder.

Porter is accused of fatally shooting 60-year-old Gary Tyrrell and killing his 61-year-old wife, Jan Tyrrell, through blunt force at their Springfield home in May.

Porter was superintendent of the Mountain Grove school district from 2003 to mid-2005, the year in which Gary Tyrrell retired as an administrator.

The two men were described as close friends, but investigators said Gary Tyrrell had recently declined Porter’s request for a $250,000 loan. Police also said Tyrrell was an avid coin collector, and that Porter had sold more than $18,000 in silver coins after the killings.