After playing the Wii game Madworld, I thought it was awesome and hilarious for its over the top violence and some of the most ridiculously cool finishing moves ever. It wasn't until I watched an online video compilation of the finishers later that I realized that Jack keeps his cigarette in his mouth the whole time. He manages not to lose the cigarette even while being punched repeatedly in the face by the final boss. Somehow, that's just badass.
Through out the entire game I was really bothered by Jack's voice because Steve Blum uses his normal smooth voice which doesn't match the face of the gruff body, it was only when it was revealed that he was the previous winner and had plastic surgery, thus explaining why the voice don't match the face!
If the last Deathwatch was in 2001, the one Jack won, why does Kreese keep mentioning games from subsequent years? (One example of several is the '07 games where he fought the Shamans.) They can't all be him making stuff up.
I think it's mentioned once or twice that they were more small scale stuff, for Deathwatches' "proper" purpose, a less bloody alternative to war.
The "real" reason is John DiMaggio was probably ad-libbing. In that stage's intro Howard mentions the manor was from "eastern Zombikistan" rather than Austria as Amala claims, too.
If it was true, it would make the doctor 8. So it's probably the ad-libbing.
While I haven't played this game, I thought Jack retired and thus wasn't present for several games and was brought back for this Deathwatch.