I know there's a special term for this issue; perhaps another teacher can recall it... Briefly:
- 1: 'A friend of + <possessive pronoun>' indicates possession or association.
- 2: 'The <noun> of <noun>' with no S on the possessor; the 'of' doesn't need reinforcing (as it is in 1)
- 3: 'A <noun> of <object pronoun> - as for 2, the 'of' is all you need.
Interestingly, 'a pessimistic view of his' would be acceptable, if the he in question had a pessimistic view of something.
Student or Learner