Vince McMahon is not only the chairman of World Wrestling Entertainment. McMahon is the czar and the king of the professional wrestling industry in North America. When the WWE defeated and then consumed World Championship Wrestling in the spring of 2001, there was no longer any real competition for McMahon and the WWE. Total Nonstop Action Wrestling/Impact Wrestling/whatever it is being called these days has never come close to being as successful as was WCW, even in the dying days of that company, and it seems as if it is only a matter of time before TNA enters the graveyard filled with departed and failed wrestling organizations.
Due to the fact that wrestlers and other would-be performers do not have another option as it pertains to a massive company that can pay out hundreds of thousands, and even millions, of dollars in salaries, some have reportedly not been keen on standing up to McMahon as it pertains to storylines and/or to their spots on cards. Having a job and being able to make a good living working in the professional wrestling industry is, in the eyes of many who are signed to the WWE, better than rocking the boat and potentially being ousted by McMahon and the company.
There have, however, been numerous cases over the years of wrestlers standing up to McMahon in one way or another. Whether or not those wrestlers “won” could be a matter of opinion. After all, not everybody who stands up to McMahon can and will win championships and be featured in a main event of a WrestleMania. For some, though, walking away from McMahon and the WWE for a period of time or even for good was considered a win, as they found happiness and opportunities after leaving the WWE. With that said, anybody who does so could eventually make his or her way back to the WWE.
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Sting routinely stood up to Vince McMahon simply by refusing to sign with the WWE following the death of WCW in 2001. The former franchise of WCW instead found a home in TNA Wrestling, a company that paid Sting and pushed him as the top babyface of that company for a good period of time. When it no longer made sense for Sting to remain in TNA, he made the jump over to the WWE. While fans may not love the way that Sting was treated in storylines until he was forced to retire, Sting was able to cash WWE paychecks and also be inducted into the WWE Hall of Fame.
14 Jeff Jarrett
Odds are that you are probably familiar with the story about Jeff Jarrett standing up to McMahon and the WWE in 1999. Jarrett refused to drop the Intercontinental Championship to Chyna before moving on to WCW unless the WWE paid Jarrett a sizable sum of money. Jarrett, per wrestling journalists such as Dave Meltzer, made six figures all because he threatened to take the belt to WCW television. While Double-J may not be welcomed on live WWE programming as of May 2016, Jarrett can boast about notching a huge financial win over McMahon.
13 James Storm
Don't assume that somebody standing up to Vince McMahon means that an argument occurred. James Storm stood up to McMahon and the WWE in 2016 when Storm reportedly turned down an offer from the WWE to rejoin TNA Wrestling. Doing so allowed Storm to make more guarantee money than he would have made working in NXT. Storm has also said in interviews that he is on good terms with the WWE and could make a return to the company at some point down the road. Turning down the WWE is not always career suicide for a performer. Good for Storm for getting paid.
12 Steve Austin
Some may forget that “Stone Cold” Steve Austin and McMahon had a falling out in June 2002 after Austin walked away from the company because he was upset with creative decisions made by the company. Austin refused to back down and just walk the company line, and he was never really buried in storylines or behind the scenes when he returned to the WWE. In fact, Austin was booked to take part in a WrestleMania feud with The Rock. That match, which took place at WrestleMania 19, turned out to be the last of Austin's career. That's a decent way to go out.
Standing up to McMahon and the WWE made Sable some money, as she and company settled out of court in 1999 after she claimed that she was a victim of sexual harassment. Sable was then featured in Playboy and she was able to land some acting gigs after she left the WWE. You can, it turns out, go home again, as Sable returned to the WWE in the spring of 2003. This return to the company resulted in Sable beginning a relationship with Brock Lesnar. Lesnar and Sable are now married, so one could say that standing up to McMahon was the best thing to ever happen to Sable.
10 Shawn Michaels
Younger wrestling fans who weren't following the WWE in the 1990s may not realize that “The Heartbreak Kid” Shawn Michaels was not always a Christian gentleman. Michaels stood up to McMahon and reportedly refused to do jobs on multiple occasions, and doing so never cost HBK his job or even the WWE Championship. If that wasn't enough, Michaels was welcomed back to the WWE by McMahon in 2002. Michaels then went on to have what many believe to be the best run of his career. Michaels and "The Kliq” made great money from standing up to McMahon.
9 Brock Lesnar
The argument could be made that nobody won by standing up to Vince McMahon more than Brock Lesnar after Lesnar left the WWE in 2004. Lesnar landed on a practice squad of the Minnesota Vikings, he received a deal to work for New Japan Pro Wrestling, he became the Heavyweight Champion of the world in the Ultimate Fighting Championship, and Lesnar then received millions of dollars to retire from fighting and return to the WWE. Lesnar has even joked that he makes “full-time money” while working a limited amount of dates in the WWE in 2016. “The Beast” has had the last laugh over McMahon.
8 The Ultimate Warrior
We may never know exactly what happened between The Ultimate Warrior and McMahon in 1996, as Warrior is sadly no longer with us. In interviews that he gave over the years, Warrior explained that he no-showed WWE events because he and McMahon had a fallen out over Warrior not receiving cuts from merchandise sales. Standing up to McMahon was the beginning of the end of Warrior's in-ring career with the WWE, but it resulted in Warrior receiving an offer from WCW. Warrior ended up getting the money that he wanted at the tail end of his career and that made him a big winner.
7 Bret Hart
Bret “The Hitman” Hart stood up to McMahon differently than anybody else featured in this piece: Hart literally punched McMahon right in the face following the events of the “Montreal Screwjob” in 1997. That had to feel like a big win for Hart, who was otherwise helpless after he was defeated in the ring by Shawn Michaels. Hart not only landed a big blow on McMahon and a big contract from WCW. After over a decade of being away from the WWE, Hart was welcomed back to the company by McMahon. The Hitman, thus, won the battle and, ultimately, the war.
6 Macho Man Randy Savage
It is no secret that McMahon did not envision “Macho Man” Randy Savage being much of a wrestler in the 1990s. McMahon had relegated Savage to the commentary booth and Savage had become somewhat of a forgettable figure when he stood up to McMahon and left the WWE for WCW so that he could continue wrestling. That was a great decision for Savage and not just because he made a large amount of money by doing so. Savage became a top performer in WCW and his feuds with the New World Order and Diamond Dallas Page were some of the best work of his career.
5 Kevin Nash
Kevin Nash was not all that miserable working for the WWE back in 1995. Nash has even stated in interviews for WWE documentaries that he was going to decline an offer from WCW until his wife learned how much money he would be turning down by remaining in the WWE. Just like Nash's good friend Scott Hall, Nash was not able to get McMahon and the WWE to match the contract that had been offered by WCW. Nash, thus, held his ground and completed the journey to WCW, and doing so made Nash richer than he ever would have been had he remained in the WWE.
4 Scott Hall
Just as with Kevin Nash, Scott Hall was not overly happy to leave the WWE for WCW leading up to his debut on Nitro in 1996. Hall was, per interviews that he has given over the years, hoping that McMahon and the WWE would match offers made to him by WCW. That did not happen, though, and thus Hall and Nash left for WCW. The rest, as they say, is history. Hall and Nash were made to be the two founding members of the New World Order, both made a ton of money, and both were eventually able to return to the WWE. Win, win, win.
3 Hulk Hogan
Hulk Hogan and Vince McMahon have had an up-and-down relationship over the years for a variety of reasons. McMahon was no longer high on pushing Hogan as the top babyface in the WWE during the 1990s, and thus Hogan and the company parted ways. While Hogan had options outside of the wrestling industry, he eventually found a home in WCW. Standing up to McMahon and refusing to ride off into the sunset made Hogan a small fortune, and Hogan proved to McMahon and to any doubters that he had plenty left in the tank as it pertained to his wrestling career.
2 Eric Bischoff
Remember that Eric Bischoff has, in the past, served as a wrestler and thus he has to be mentioned in this list. Yes, Bischoff and WCW lost the Monday Night War to McMahon and the WWE, but Bischoff nevertheless won and won big by standing up to McMahon. Bischoff earned himself a ton of money by standing up to McMahon, as doing so made him a brand unto himself who was able to sell copies of a successful book and earn gigs from the WWE and TNA Wrestling. WCW may no longer be around, but standing up to McMahon was the best business decision that Bischoff ever made.
1 CM Punk
How exactly did CM Punk win after he stood up to Vince McMahon and Triple H in 2014? For starters, Punk earned himself a contract from the Ultimate Fighting Championship. Punk has also been featured in a UFC video game. The “Straight Edge Superstar” does not even have to ever have a match in the UFC for his journey from the WWE to have been worth it, as he could write his own ticket and make money completing a short stint on the independent wrestling circuit. Besides, you just know that McMahon would love to bring Punk back in an attempt to attract viewers and attention. That, in a way, would make McMahon the real winner; as he usually is.
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