I was initially confused. I read that you were looking for a really, really good cigar, and a few choice sticks came to mind. Then I read on, and you clarified in wanting a really really really good cigar, which completely changed everything.

My short list:
Padron 1926 Anniversary maduro
Diamond Crown Maximus
DPG My Father (seems appropriate)

If I might also say, you might want a cigar that you know you will enjoy. No sense in spending money on an unknown cigar if you are looking for enjoyment. Get something you like.

I lost a very close friend this past Christmas. I go and smoke a cigar at his grave site once a month. It's not always a great cigar, but it does me some good. I'm sorry to hear of your loss.