The 18-wheeler was carrying close to 40,000 pineapples just before 11 p.m. in the northbound lanes when the big rig experienced a blowout.
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The truck swayed, ripping away from the tractor. The trailer then hit the center divider wall and rolled over into the southbound lanes.
At the same time, a second big rig, which happened to be carrying new 18-wheeler parts and was on the way to Houston, was also in the southbound lanes and ended up crashing into the trailer laying on the roadway.
The impact ripped the trailer open, scattering pineapples across the southbound lanes.
On top of that, engine oil was dumped onto the freeway in the crash.
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The driver in the original 18-wheeler that had the blowout was taken to HCA Conroe hospital.
The crash shut down the freeway until just before 6 a.m., but the lanes are back open.
Texas DPS is investigating.