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He argued $63.3 million dollars was too much for the murder of a UK football player, but Wednesday a Fayette County judge told admitted killer Shane Ragland it's time to pay up.
The judge upheld a jury's civil award for Trent DiGiuro's family.
Shane Ragland's attorney asked for that decision to be thrown out, arguing it was excessive, saying the man who'd spent seven years in prison before his conviction was overturned couldn't afford it.
Judge Thomas Clark overturned that request.
Ragland pleaded guilty to 2nd degree manslaughter in 2007 for the sniper-style shooting of Trent DiGiuro back in 1994.
"To lie in wait, in the dark of night, and assassinate a person for purportedly being blackballed from a fraternity years earlier, the court can find no greater reprehensible conduct," Judge Clark wrote in his ruling.
Ragland was convicted of murder and sent to prison in 2002, but that conviction was overturned by the Kentucky Supreme Court in 2006.
Ragland's attorney, who we tried to reach for comment, has 30 days to appeal the ruling.