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Police say a westbound tractor-trailor unit jack-knifed about 30 kilometers east of town around 1:00 last night.
It was struck by an eastbound semi, which was unable to stop, due to slippery road conditions.
The driver of the eastbound unit was killed in the collision.
In the meantime, two more transports also collided with the other two semis.
Earlier in the evening, the OPP say there was also another roll-over on the Trans-Canada east of Kenora near Chadwick Lake.