To write a condolence letter concerning someone to whom one was sympathetic, or with whom one had shared pleasant experiences or had experienced a feeling of commonality, is one thing.
But what about the problem of writing a condolence letter to the bereaved that focuses on a person you consider to have been a total son-of-a-bitch, or an absolute idiot, or something else unpleasant?
Such letters can be difficult to put together in a manner that is sincere but that does not at the same time sound either callously condemnatory of the deceased or unfeeling towards the recipient, or both.
After all, it is hard to mention, for instance, the dead person's local reputation for preying on underage girls without also appearing to imply that the recipient bears some degree of guilt by association; meanwhile, not to allude to it at all would smack of glib pollyannaism.
Perhaps the best thing may be to mention the problem area, but in a subtle way that effectively labels it merely as ‘controversial’ or ‘contentious’.
First of all, I want to express to you my heartfelt reaction on hearing of the death of your Uncle Jack. I know he was very important in your life, as he was in mine.
Like you, I recall him from our teenage years, in particular one stand-out occasion when (at his request) I helped your uncle jack off a horse. That was certainly a seminal event which I am highly unlikely to forget. I recall also his generous acknowledgement of all the personal errands and services we both rendered him over the years.
Meanwhile, I know his former neighbours frowned, to put it mildly, on his habit of regularly dispensing $20 bills to all the children in our street in recognition of the many little things we did for him; but those days were long ago, and I feel it is now time for everyone to move on.
Evidently Jack felt this more strongly than most, and is the first to have taken appropriate steps in that direction.
With much love and all best wishes for the future, however doomed it may turn out to be,
Your fond friend
This is the place to post questions and discussions on usage and style. The members of the Wordwizard Clubhouse will also often be able to help you to formulate that difficult letter.
End of topic.