#2 "Dr. Death" Steve Williams
Three words - Brawl. For. All.
At the time of his signing in 1998, "Dr. Death" Steve Williams was one of the toughest men in the business. He had previously gone unpinned in North America for almost a full decade, he was involved in three matches that were rated 5-stars by Dave Meltzer, and he was one of Japan's most feared gaijins. Naturally, WWF's first thought was to book a shoot-fighting tournament in an effort to get Williams over as a contender to Stone Cold Steve Austin's WWE Title.
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And then it all went wrong. In just two rounds.
After handily defeating former Quebecer Pierre Carl Oulett in the first round of the tournament (which they called the "Brawl For All"), Williams was set to face the lesser-known half of the Smoking Gunns, Bart, in Round II. Some have said that WWF officials were so confident in Williams winning the tournament that they paid him the $100,000 grand prize money prior to his fight with Gunn. Unfortunately for them, at some point during the fight, Williams suffered a torn hamstring and was unceremoniously knocked out by Gunn. The injury would sideline Williams for several months, and he was eventually released following a brief run with Jim Ross as his manager.
Without a doubt, the Brawl For All was one of the stupidest things that WWE ever did. The fans hated it, several wrestlers went down with injuries, and they ended up jobbing out the winner of the tournament to Butterbean (an actual boxer) at WrestleMania XV. On paper, maybe it sounded like a good idea, but in practice, it did far more harm than good. The tournament was especially disastrous for Williams, who apparently never forgave former friend Jim Ross for involving him in such a dumpster fire.
Personally, I would have loved to see Steve Williams vs. Steve Austin. Sadly, it never came to be.