Winchester Man Sentenced for 2016 Fatal Crash

Timothy Stephen Anderson, 58, of Winchester, this week was sentenced to serve 12 months in jail after pleading guilty to reckless driving in a 2016 crash that killed the driver of a tractor-trailer.

The crash happened on Dec. 12, 2016, when Anderson exited the Stoneleigh subdivision west of Round Hill and drove his Toyota Corolla into the path of a tractor-trailer driven by Thomas D. Taylor, 36, of Timberville. Taylor attempted to swerve out of the way but the 2005 Mack tractor-trailer struck the front of the Toyota, turned on its side and then flipped back on its wheels and jackknifed. The engine compartment and cabin of the truck became fully engulfed in flames and Taylor died at the scene.

Anderson initially told investigators that he was attempting to turn around and had not seen the oncoming traffic. Deputies later learned that he may have been attempting to take his own life so that his family would benefit from his life insurance.

He pleaded guilty to reckless driving in January.

In Circuit Court on Wednesday, Senior Assistant Commonwealth’s Attorney Ryan W. Perry asked Judge J. Howe Brown Jr. to hand down the maximum 12-month sentence. “Either way the level of recklessness there is obscenely high, and it cost a man his life, it cost his parents their son, it cost his children their father, and it cost his fiancée an entire life without her betrothed.”

Timothy Stephen Anderson

Brown agreed.

“No sentence will bring Mr. Taylor back. No sentence will really impact the defendant any more than what has already been done. So very frankly, without meaning any disrespect to either party, my focus is on the public, on people who will learn about this,” said Brown. “The word will get out what was done to this man who was so reckless and in such disregard of human life that he pulled out in front of a truck.”

“Maybe one person seeing this sentence will say ‘I better pay a little bit more attention’ and we will save one life,” Brown said.


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