I had a chief who became chief at 14 and died at 75, so he was chief for 61 years. The award for long reigning chief didn't highlight!!! Has this happened to anyone else?

I had the same thing happen. He became a chief at 19, and died at 79. 60 years and no Legendary Leader.

Hmm, no-one else has had this problem?

What version of the game are each of you playing (check the menu screen of your game)?

Also, did any Island Event occur that involved your chief?

I'm having the same problem!! I've had the same chief since beginning of the game! Event showed 1 Isola year, I just completed my Aromatherapy at 58 Isola years. I have the newest version of the game, and have not had any events happen to my chief.