Often refers to actual physical location, being the last in line. During the parade, the clowns entertained the crowd while bringing up the rear.
Pro Tip 2/3
Not Negative
The phrase isn't always negative; it can just state a fact, without implying failure. Even though he was bringing up the rear, his fans cheered him on enthusiastically.
Pro Tip 3/3
Idiomatic Usage
Understand it's an idiom; don't interpret it literally, like physically moving someone's rear. When we reached the summit, I realized I was bringing up the rear of our group.