Thanks everyone. You were collectively correct.
I pulled the roller apart and the bushing was toast!
(For reference: Part # DeWALT Bushing - 5140010-92)
The roller looks to be straight and the bushing is the only obvious defect so hopefully that'll be an easy fix.
The pictures show the bad bushing next to its counterpart on the other side of the roller for reference.
I'll let you know when I get it put back together just for follow up.
For every complex problem there is an answer that is clear, simple and wrong.