MARTINSVILLE, Va. – 27 years and still going strong. Martinsville Sheriff Steve Draper is the longest-serving sheriff in the Commonwealth. Over that time, he has made improvements to jails and inmate workforces as well as introduced an EMS program. When he first started as a sheriff in 1994, he was assigned number 121 out of 123 sheriffs. “To look back and see that 121 and then to look and see this one.