With that much paint transfer, your clear is probably damaged. That said, WarWagon's advice is strong. The caveat is that you should be EXTREMELY careful when messing around with anything abrasive and your paint.
Realistically, it is a coupla hours worth of repair, a bumper cover R&I (remove and install), and a coupla hours worth of paint to do it right, if you cannot remove it with some rubbing compound or whatnot.
So your options are:
1) Do it yourself. This means taking a chance with a fairly expensive finish.
2) See if a Detailer can do it. A better option, as a good detailer is used to taking a finish to the edge of damage, and then making it look lovely afterward. Still, you take the chance that they will not be able to do it, and you will wind up paying for Option 3 anyway.
3) Take it to a bodyshop and have it done right.
Lastly, make very sure that your headlight did not take a knock. The direction of damage leads right to your liht. It is entirely possible that the storage box hit your grill. When that happens on Trailblazers, you frequently see cracks on the backside of the headlight. Basically, you give a good strong shaking and see if there is any movement.
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