A man won $11 million in a lawsuit against police after his conviction for killing a Missouri newspaper’s sports editor was overturned, but the city’s former insurer resisted paying most of it for almost three years. A Missouri judge this week ordered the company to pay nearly $44 million.

Most of the money would go to Ryan Ferguson, whose legal battle with Minnesota-based St. Paul Fire and Marine Insurance Co. in Missouri’s courts started in 2017, about six weeks after he won a federal lawsuit against six Columbia police officers. Ferguson was convicted in 2004 of killing Columbia Daily Tribune sports editor Kent Heitholt but was released from prison in 2013 after a state appeals court panel concluded that he hadn’t received a fair trial. Ferguson maintained his innocence.

The city insurer paid Ferguson $2.7 million almost immediately after he won his federal lawsuit, and his attorneys expected St. Paul to pay $8 million under its coverage for the officers from 2006 to 2011. But the company argued that it wasn’t on the hook because the actions leading to Ferguson’s arrest and imprisonment occurred before its coverage began.