From what I understand, HM's have received personal letters from their families. The task is to find a HM's letter from a pile and either shred it or give it to them. If you shred it, the HM is out of the captaincy race but if you give it to them, they're a captaincy contender.
Here's the catch. Family letters mean a lot. Lots of emotion, sentiments are attached to it. Some people have saved letters from decades ago. And in the technological savvy world their value has gone up even more.
A savvy player would not bother competing for captaincy in this task. This is a prime opportunity to look extremely good in the eyes of the neutral fan, the majority. On the other hand tearing someone's letter will bring a lot of negativity.
It's a googly. Interested in seeing who the real game players are.