Mechanics of a grappling chain

If I grapple a creature that is already grappled by someone else and pulls them away, are they freed automatically? Or are they dragged along?

Same question if I grapple the grappler instead.

Bob the barbarian is grappled by Doug the Druid.

Wanda the wizard wishes to grapple Bob

Bob would make a ste/dex saving throw against Wandas grapple dc (8+strmod+pb).

If Bob qnd Wanda are allies, Bob could choose to fail the save and be auto-grappled by Wanda. Dont remember if the rules allow Wanda to move bob away from Dan or if there is some contest there as well.

If Wanda has Telekentic feat, Wanda could do a telekenetic push against Bob, he can auto-fail his save, Wanda pushes him 5 feet, and if that is beyond the Reach or Dan, then Dan no longer grapples Bob.

Theres def some weird stuff going on with grapplling, pushing, and forced movement.

Raw, if Bob was grappled by a Kraken (str=30?), and Wanda telekinetically pushes Bob, Bob can auto fail his save and be pushed away from the kraken, freeing Bob.

I would think the kraken would have a say in the saving throw, but raw i dont think they do.

Let say nobody has the Telekinetic feat. I'm only using the forced movement from the fact that you can drag a creature that you're grappling as you move. And no, there are no contested checks in 2024. They've all been removed. So the rules here are uncertain. That's why I'm asking.

I mean, i think raw would say if you are grappled by a kraken, if i push you (unarmed strike option), then you could choose to fail, and i push you 5 feet, and if its out of the krakens reach, you are no longer grappled by the kraken 

I dont think there are any rules, raw, that would say my push has to overcome the kraken that has you grappled. My push just has to overcome your resistance, and if you choose to fail, i push you 5 feet, and right out of the krakens tentacle.

I dont know if thats how i would do it in my campaign (im in the middle of a 2024 campaign and nothing like that three-way-grapple has happened, and my players have fought a kraken) but i believe thats the rules.

Yeah, the RAW doesn't outline anything about maintaining the grip against an opposing force aside from an escape attempt by the grappled, and it does explicitly say that the condition ends if the target leaves the grappler's reach. Ergo, by RAW you can attempt to grapple a friend, they can choose to fail, and the friend can pull you free. Rather cheesy, but seems to come together.

Personally I'd suggest DMs call for an escape check with advantage and/or allowing the two to pick the character with the better mod for the roll if there's a size category difference in favor of the grappler, but that's just a personal take.