About a year ago, I had given one of the guys at work the necessary class to get his carry permit. When he sent in his application, the chief of police in his town (in MA the town police issues the permit after having the State Police do the necessary checks) had him come in for an interview. He had a couple of blemishes on the application for driving under and possession of pot while in college. Both were continued without a finding, so they should not have played a part in the decision. However, the chief rejected his application, based on his being an "unsuitable person" without even forwarding the application on to the State Police for research.
Fast Forward to this year. The chief is gone due to numerous issues in town. It is unclear as to whether he left voluntarily, or was pushed out. I strongly suggested to my friend to re-apply for the permit. In just over two weeks he has his permit! Now he's shopping for a 1911.