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Who do you think will win?

I'm going with Squeezeplay.

He's stronger and more durable.

Squeezeplay.

Skullgrin's nothing without the Pretender shell.

In the TFU tech specs, Skullgrin is stronger and more intelligent. He is a Pretender so he can basically split into two warriors although it is more difficult to control two with one mind. At first glance, one would say that he'll win this.

On the other hand, Squeezeplay is a Headmaster with the skill and intelligence of two minds. He also has a rifle that disrupts electrical flow and equipment. I'm not sure if that ray can penetrate Skullgrin's tough shell.

Both are hardcore warriors. Skullgrin is built for land combat while Squeezeplay prefers liquid environments: seas, lakes, rivers, etc. The environment is very important in this relatively even match.

Squeezeplay works as a saboteur so he could use his skills to set a trap for Skullgrin. This would be known to Skullgrin, who would anticipate and counter it.

On the balance of probabilities, Skullgrin would attack directly and overpower Squeezeplay before the saboteur could mount an effective defence. Sorry Squeezy!