6 Degrees of Separation

[William Cloud Hicklin]

I'm pretty sure G did- but then, so did Ugluk! Although it appears nowhere in published writings, in his time-schemes Tolkien wrote that Gollum, while lurking outside Lorien waiting for the Company to emerge, was captured and questioned by Ugluk's team from Isengard (Saruman had been alerted by messengers from Moria that the Coy had passed through).

Anyway, I'll call that a win, although what I had in mind was a bit more roundabout:

1. Sauron was a Maia of
2. Aule, who was married to
3. Yavanna, who obliged Saruman to bring along
4. Radagast, who sent out
5. Gwaihir, who was spotted by
6. Legolas