DW also had a bet with Sakakibara that Liddell would win the tournament.
The UFC and PRIDE were trying to co-promote (yes, really) and send fighters to each others organizations. So they had DW guest comment on the Liddell vs Rampage fight. DW also had a bet with Sakakibara that Liddell would win the tournament.
Of course, with PRIDE never sending any fighters to the UFC (despite Takada going on a UFC PPV and announcing that they'd "send Sakuraba and Fujita to the octagon."), you can chalk that up as to one of the reasons why the UFC doesn't co-promote anymore.
He wasn't a commentator. He got on the mic for that fight (and a couple others) because he brought Liddell over to enter the tournament on behalf of the UFC.
It pissed me off that they never let Sakuraba go to the UFC. If he could've made 170 Penn vs Saku and Hughes vs Saku would have been awesome.
I thought the bet was Wanderlei vs Chuck, but it never happened since Chuck got TKOed by Rampage.