Bossman takes this. Jake Robert was a good wrestler, but Bossman was tons better, in my opinion. He has the strength advantage, is very quick for a big guy, and he's smarter then Jake.
Jake Roberts always gets credit for having such great psychology, both kayfabe and shoot, and in kayfabe wise... his psychology edge was always nothing but having a snake to scare his opponents. And I guarantee Bossman wouldn't be scared of a fucking snake. In fact, dealing with the Bossman, Damien suffers a worse fate then he did when the Earthquake got a hold of his ass.
Jake might have a win over the Bossman in the past, but I'm sure even if that's true, Bossman wasn't in his prime at that time, and this tournament is based on wrestlers in their primes. And in his prime, Roberts couldn't fuck with the Bossman, kayfabe AND straight up talent wise as far as I'm concerned.
Bossman should definitely take this. Jake Roberts career was full of "Would've", "Could've", and "Should've's". He didn't ever reach his full potential and if he had, then he may have stood a chance. But since he didn't, Bossman should take his ass out.