The crash happened in the southbound lanes of Route 1 at Fieldsboro Road around 5:15 a.m.
Police say a tractor trailer was traveling southbound on Rt. 1 in the right hand lane when it was struck from behind by a box truck driven by Ian McPheeters, 24, of Wilmington.
It took responding emergency crews approximately 2.5 hours to free him. He was then transported by State Police helicopter to the Christiana Hospital where he was treated and admitted in critical but stable condition with multiple injuries.
The driver of the tractor trailer was not hurt.
Route 1 southbound was closed for about seven hours in the area, but re-opened shortly before noon.