Rapple – Can a giant squid draw the creature?

I'm new to D & D, I want to try something, but I do not know how a key component of my plan works. I tried to search it in PHP, google it, but no luck.

Suppose I have giant octopus (large size) on the mainland, he has a range of 15 feet, he attacks a man who is fifteen feet further, and he managed to grab this human (medium size). Can an octopus attract this human?

a) 10 feet to his neighbor field?

b) in his own field?

Just to describe what I'm trying to do …
I always liked unorthodox tactics, ok, I know that I am a new player. Maybe I should learn orthodox things first … but I like to play this way. I'm Moon Druid Level 6, I'd like to summon 2 giant caterpillars, then Whild Shape to Giant Elk (maybe Ritual Speak with Animals and Longstider on himself before that) and finally put Kraken on my back. Giant Elk Speead is 60 feet, I would skip the initiative to be close to the Kraken, then I would move close to (10 feet) at my enemies and perform the Bead action immediately after the Octopuses. The general idea is to grab someone and disconnect, and then hit 3 to 1 … yes, I know 🙂 🙂 🙂 🙂