10 Most Vicious WWE Grudge Matches Ever

2. Stone Cold Steve Austin vs. Mr. McMahon - St. Valentine's Day Massacre

The story of Austin versus McMahon was a goldmine back in the late nineties. As much as the roster at the time was top-heavy with main event level talent, this was the feud that formed the backbone of the Attitude Era.

The central conceit of the thing was that Austin was the most popular guy in the company and Vince McMahon's golden goose, at a time when they needed every penny they could dredge up. So Austin held the company's fortunes hostage: he had to be promoted in the main event, but he refused to play the corporate game.

The key thing to the Austin/McMahon dynamic was careful escalation. Neither man would ever back down, but the tyrannical McMahon wasn't a wrestler, no matter how jacked and intense he was, and they couldn't promote the feud like an ordinary angle. So there would be beatdown storylines and surrogate McMahons: Mankind, The Rock, The Undertaker, whoever could step into the boss' shoes and force Austin to capitulate.

But at some point, for the blow-off, it had to be Austin and McMahon in a ring together.

Austin finally blagged the match with his hated boss that he'd been after for so long at the St. Valentine's Day Massacre event. He used McMahon's hatred of him as the hook, and his WrestleMania title shot as bait, making his boss an offer he just couldn't refuse: a steel cage.

In the end, the beatdown was almost entirely one-sided: most of it took place before the match even began, and Austin was nearly declared the winner through stoppage before the first bell. McMahon's ace-in-the-hole was the debuting Paul 'No Nickname' Wight, who ripped a hole in the canvas to come up from below. The future 'Big Show' threw Austin into the cage wall several times: the final time, the cage panel simply busted open, swinging to the side to allow Austin to escape the cage and win the match.

Austin and McMahon weren't done there, not by a long shot. However, the angle had been running at a breakneck pace for nearly eighteen months by this point, taking over the lion's share of WWE programming, and was beginning to lose all logic and narrative coherence - this was the Attitude Era after all, the era of 'Crash TV'.

The cage match at St. Valentine's Day Massacre was probably the final time that the feud made any sense: before the Corporate Ministry and the Higher Power, before multiple McMahons began trading ownership of the company and before Austin's infamous and poorly-conceived heel turn at WrestleMania X-7.