frequent flier
n.— «Bernier is near the top of a list of about 475 “frequent fliers,” the term a consultant used to describe people like him, many of whom pose little threat to the community yet cycle in and out of jail with no apparent hope of changing their ways.» —“Locked up in a cycle” by Mike Saewitz Sarasota Herald-Tribune (Florida) Apr. 17, 2005. (source: Double-Tongued Dictionary)