Getting involved with cops' investigation during their case wasn't the brightest idea but hey! Where there's trouble, there's a Winchester. That didn't end well. They were caught with their fake FBI badges and Dean's shoulder got shot as they were running.

Everything resulted to them getting busted and thrown in a cell.

"Ow!" A low hiss of pain escaped Dean's lips as Sam pressed the piece of fabric against his shoulder to stop the bleeding.

"Don't be a wuss." Sam said, applying pressure.