Vince McMahon probably still considers winning the Monday Night War his greatest accomplishment outside of creating WrestleMania and in a way he is correct. From the depths of 1995 when WWE's revenue and attendance figures were reportedly as low as they ever were Vince was able to create new stars and overhaul his wrestling empire to become the greatest and largest 'Sports Entertainment' juggernaut the world has ever seen. He not only outlasted and defeated his major and minor competition in WCW and ECW respectively, he purchased both and by 2001 he was riding the wave of conquering wrestling all over again.
Not everything has gone Vince's way since that monumental victory during 2001, with several major shifts in company philosophy and management leading to persistent problems and losing that 'must-see' aura WWE had for The Attitude Era. Some other minor problems were out of their control but even then the roster should have been able to bear the burden with the influx of great talent from the two defeated companies.
Since the Monday Night Wars ended no one is going to claim that WWE has been anywhere near perfect and at a lot of times quite the opposite was the case, with WWE squandering huge opportunities and seemingly deadset on paths that nobody was enjoying watching. Paths that not only shed die-hard and lifelong fans by the literal millions but grinded great talents beneath the road Vince McMahon was paving. WWE made many mistakes post-Monday Night Warfare and these are the biggest mistakes that held them back and even some which continue to plague WWE.
18 All McMahons All The Time
One of the key successes to the Attitude Era was the influence of all four of the McMahons at various stages. Stephanie getting kidnapped, Shane as a crooked referee and then a spoiled son, Linda as a foil here and there for Vince's lechery, not to mention Vince's massive contributions himself. The lesson Vince took from this was that at all times his family is the biggest draw WWE has, and if that was ever true at some stage it's long passed it's point of value.
If you include Triple H in the McMahon saga there is probably not a time you can point to since the Monday Night War where McMahon shenanigans didn't dominate a portion of the year and particularly at WrestleMania. Even recently Stephanie and Triple H have re-emerged to pollute RAW as we get close to the Road To WrestleMania and no one is looking forward to it.
Only Shane really gets a modern day pass because of his selfless risk-taking and putting his body on the line which balances out the equation. Vince himself is a rare occurrence but even now he has a gravitational pull that make entire shows revolve around him for better or worse.
The sooner WWE finds the courage to let its wrestlers star at that important level currently reserved for McMahons and part-timers the sooner WWE will regain lost fans.
17 Triple H's Reign Of Terror
When a wrestler's tenure on top is so unbearable that it gains a common nickname from the fanbase there's little doubt that it is a huge mistake. Usually when a wrestler is on top for an extended period of time it's a face superstar riding the wave of their popularity but in this case, it was Triple H crushing the fans' goodwill and patience under his boot every Monday Night Raw.
The Reign Of Terror is responsible for several of the less popular format choices we still see today. The 20 minute RAW opening promo. The dominant but tedious to watch heel champion for far too long (Jinder Mahal). The heel Authority Figure may have begun with Eric Bischoff and Vince McMahon but it was the Helmsley-McMahon Regime that made it boring and predictable. Between his backstage influence and new McMahon familial connections he was in a position that corrupted the process all around him.
From about 2002 through 2005 Triple H was either the centrepiece or outright champion on Raw, whether we wanted it or not. He beat and belittled dozens of potential moneymaking superstars and by the time it was all over the only beneficiary was Batista and to a lesser extent Randy Orton. Funny how his handpicked friends made it and the others 'didn't have what it takes'.
16 Wrestlers Burning Out
From Jeff Hardy to Kurt Angle to Brock Lesnar and countless others, WWE grinds their wrestlers for every bit of their time that they can, meaning that if you're not built for a near-constant life in wrestling, foregoing your personal life, living on the road, you're going to have a bad time.
Kurt Angle essentially worked himself into a wheelchair, competing no matter the severity of injuries he sustained out of an insane dedication and work ethic that should've been curtailed for his own good. Brock Lesnar was a megastar that WWE didn't realize was more suited to a lesser schedule and so he left WWE within two years of his debut out of frustration and exhaustion with the company. Jeff Hardy succumbed to his lifestyle of pills and drugs to the point he had to leave WWE for his own sake. The list goes on to today with certain superstars electing to not even consider working for WWE anymore due to the never ending schedule expected of its contracted workers.
WWE is proud when they can say that "they never have an offseason" but for the talent, this is a very real issue they have to reconcile with. It will come to a head again this year when RAW films live on both Christmas and New Year's Day for the first time, making demands of its wrestlers that might just be too much for some.
15 DDP: Stalker
DDP should have been a centerpiece of the WCW invasion angle alongside Booker T, no question about it. If WWE simply couldn't wait for the other major WCW stars hooked into guaranteed Time Warner contracts to become available for The Invasion, then DDP, as the one star who forwent his big contract to be involved early should have been treated like royalty. That did not happen.
Not only was DDP's storyline as a stalker to The Undertaker's wife badly mishandled (not to mention nonsensical for a man married to Kimberley), but it effectively sidelined DDP from the central storyline. He was badly embarrassed in matches against The Undertaker and Kane and never involved as a WCW mainstay, which he should have been from the beginning.
DDP also received harsh criticism from WWE superstars for trying to plan matches rigorously which alienated several wrestlers and only further dug him a hole. DDP still had value but WWE and their wrestlers didn't give him a real chance, and so a bankable WCW Champion was wasted. Surely a meeting of WCW's People's Champion and WWE's People's Champion writes itself?
Since WWE went public and partnered with several toy manufacturers and merchandise distributors they've found that these companies and their shareholders aren't as concerned with the quality of the product as they are return on investment and avoiding controversy. Avoiding that controversy entailed WWE becoming a TV-PG product and while it's perfectly possible to create compelling television under the PG restraints, WWE elected to become cartoony and childish at their own expense.
You could point to John Cena alone and make this complaint, since going from a rapping wordsmith who consistently entertained the majority to a childish buffoon essentially forced fans to hate him and turn off WWE for good. The intensity in matches dropped. Promos became stilted and pre-written instead of alive and visceral. Weapon matches became somehow less violent than regular matches. Blood disappeared from WWE television except in rare cases where they forcibly stopped matches to clean it up, garnering impressive, arena-shaking boos.
The overall effect was that whether WWE had to go that far in softening their product or not, they did and it again led to large portions of fans becoming former fans.
13 Scott Steiner
WCW's last great creation before going under, Scott Steiner as the chainmail wearing Big Bad Booty Daddy was gloriously entertaining in an unhinged way and should've had a huge run in WWE off the back of that. That was not to be as circumstance, injury and personal issues crippled his WWE return.
Steiner came to WWE after sitting out The Invasion so he could collect on his massive WCW contract. Once that finished he came in with a huge impact while rolling into the 2003 Royal Rumble with a World Championship match against Triple H, who was right at the start of his dominance. A lingering foot injury and perhaps the greatest lack of chemistry ever seen between main event competitors led to an abysmal match and an only slightly better but still awful rematch the next month. Steiner couldn't gain the World Championship and the terrible matches led to WWE dropping him way down the card. Steiner has accused Triple H of sandbagging him which only furthers the rift between the two sides.
Steiner's WWE stint ended within two years, signaling another major WCW star that WWE burned through without reaching a fraction of their potential.
12 The nWo reunion
Some ideas are better off in the past and considering how bungled the WWE's interpretation of the nWo was from the get-go, this was one of those times.
For those who knew the nWo, they were either a super cool mid-90s faction or a cancerous blight on late 90s/2000 WCW. Neither of those things showed up to WWE, with Hogan, Hall and Nash cutting a bizarre thankful promo to Vince which undercut whatever danger and threat they were supposed to be introducing. Hall was in the midst of his alcohol fuelled downward spiral and Nash was in worse physical shape than Hogan due to injuries so by the time WrestleMania rolled around it was only Hogan's gravitas that saved the match with The Rock. The nWo might as well have not existed for the way the crowd reacted to The Hulkster. That night the nWo was severed beyond repair even as it limped along adding and culling members like Big Show, X-Pac and Booker T.
The final nail came when Kevin Nash returned from injury only to collapse within seconds of being tagged into the match, effectively ending any nWo remnants and shelving the group from modern relevance.
11 The Mishandling Of Stone Cold Steve Austin's Walkout
During the ascension of Brock Lesnar Vince McMahon informed his biggest superstar Stone Cold Steve Austin that he was expected to lose on television to The Next Big Thing with no buildup, no story and without it being a 'big money' match. Stone Cold saw this as another insult to his flagging status in WWE after the WrestleMania mid card match with Scott Hall and so he walked out. WWE and Vince made the story into "Stone Cold took his ball and went home" during Austin's absence but the truth lies somewhere in the middle and should have been avoided.
McMahon is notorious for being singleminded when he's trying to make someone into his new cash cow and clearly Lesnar was the beneficiary in this case with Austin seen by McMahon as last year's model. Austin wanting to preserve his status and make a big money match out of it, one that fans would've certainly wanted to see, makes a lot of sense but was discarded by Vince's laser focus on Brock. If either side, particularly Vince, had had the nuanced discussion to lay out a compromised course, WWE wouldn't have had to go through another case of a major star walking away. It persists even to today with CM Punk, Neville and others realizing that their power lies in their compliance or lack thereof.
Austin has since called the walkout one of his biggest regrets, citing leaving money on the table for that opinion, but it was a case of two sides unable to reach common ground and it was the fans who suffered for it.
The zombie that showed up on the first weeks of WWE's version of ECW was prophetic because rather than the original extreme promotion having a glorious rebirth, this ended up being the shambling corpse of a long-dead idea trotted out to rot under the bright lights.
When WWE announced that ECW was going to have a second One Night Stand PPV in 2006, and that it would be the official revival of an ECW branded wrestling show their fans were mostly elated but skeptical. The skepticism soon became dread and resignation as 'WWECW' hardly resembled the ECW of old and had silliness in place of anything 'hardcore'. A Batista V Big Show match in the Hammerstein Ballroom got such vitriolic boos that WWE only went further away from original ECW, making the problems worse.
Aside from a few bright spots like CM Punk, Sheamus, Kofi Kingston, Christian and Miz & Morrison, WWECW's legacy was of failure. This was epitomized by the December To Dismember PPV which showed Vince's contempt and disregard for the true nature of the revived brand, which soon had its final death before being replaced by NXT.
9 Burying WCW
Vince has an internal and ever-present hatred for anything WCW, and even when he finally defeated the rival promotion and he could have made more money off of them under his control he elected at every turn to bury them to re-establish his dominance like an insecure bully stomping on your wallet after already taking it. WCW never stood a chance and watching any WCW talent once they joined Vince's world they were ritually subjected to a course of humiliation before ever getting a fair shot.
The trend has continued even to today, with stars such as Booker T and Sting both being beaten by Triple H at WrestleMania long after the war was over and WWE had no reason to belittle these wrestlers further. In fact, if you envision Triple H as Vince McMahon's surrogate, on PPV he's beaten so many former WCW stars and champions that Vince would be a grand slam champion of that company.
8 The ECW Originals
WWE had all of them at various times, and every one of them was wasted in some way. However they were featured in the original ECW, they were tiered separately within WWE and almost all of them had short stints before being kicked to the curb.
Lesser stars like Balls Mahoney were ritually fed to WWE stars like Big Show. Mid-level stars like The Sandman and Raven weren't treated like the big deals they were in ECW, instead featured as voiceless hardcore types to be abused for a while and then forgotten about. The few ECW stars to even be considered big-time in WWE such as Rob Van Dam could at best hope for some sporadic title shots or token reigns, but never were shown to be major players.
Considering the wealth of talent who went through the original ECW en route to WCW and WWE, it's a shame the originals who stuck it out or were painted with that same brush were so marginalized.
7 Turning Goldberg Regular
The wasting of Goldberg was such a legendary failure that it prompted Goldberg himself to want to return and properly finish his wrestling career this year. When a run is that originally bad you know it deserves to find its place on this list.
Goldberg sat out the remainder of his huge Time Warner contract as many other WCW stars did, coming to WWE in 2003 the night after WrestleMania to feud with The Rock. The hot start was the best it ever was as Goldberg soon ran into Triple H at his dominating worst, murdering his mystique and momentum for his own benefit. Fans cooled on Goldberg and only then did WWE pull the trigger on his World Championship run but it was too late.
Finally, WWE's lack of planning and respect for Goldberg's status led to him and Brock giving one of the worst Wrestlemania performances of all time at Wrestlemania XX, both leaving the company and happy to do so.
6 The Devaluing Of The Cruiserweight Division
If you were wondering why WWE had to reintroduce the Cruiserweight Division the last couple of years it's because they absolutely butchered the version they had after they acquired WCW and ECW.
WWE's original Light Heavyweight Championship was hardly ever featured and so when they had an influx of WCW cruiserweights they used WCW's championship instead (a super-rare occurrence) and had guys like Rey Mysterio and Tajiri competing in show-stealing matches for the title. This lasted a few years with the title a SmackDown regular, but it gradually got used for comedy, as a prop and eventually a joke. When Chavo Sr. won the title, Jacqueline (who can wrestle but reappeared and disappeared without reason), and finally Hornswoggle, it was all over.
By the time the Cruiserweight Championship was stripped from Hornswoggle it was firmly established as a worthless sham championship, and for the legacy of the superstars who held it, it was an insult. Fingers crossed for the current version to avoid this fate.
5 Failing To Keep The Rock In The Fold
This may have been inevitable due to The Rock's insane levels of charisma, looks, and attitude but the taste of Hollywood he got from The Mummy Returns and his own starring role in The Scorpion King saw him effectively end his full-time wrestling career in 2003. When his contract expired in 2004, the WWE didn't re-sign him as a part-time talent, at the time insisting their stars remain full-timers (boy, that tune changed).
Despite showing up very irregularly for the next few years The Rock completely distanced himself from wrestling, due to a combination of his Disney movie persona and WWE's crass output at the time that no one wanted Rock to be associated with. Moreover The Rock's lingering effects on WWE television came through with Vince trying to make John Cena into a Rock clone except with his lack of similar talents making him appear the cheap copy. This only further alienated The Rock and instead gave impetus for their feud after WrestleMania XXVII when Rock finally 'returned'.
Vince could've done more to keep The Rock in the fold but between Triple H wanting to hold the world titles to ransom, his greatest rival Stone Cold also ending his career, and Hollywood looking at any wrestling association as a negative, WWE fans were effectively denied Dwayne Johnson for most of a decade.
4 Raw Guest Hosts
Outside of a tiny handful of comedy segments that worked, such as Bob Barker's Price Is Right and The Muppets, the guest host era of Monday Night Raw was among the worst the show ever had. It began with the infamous, fake 'Trump buys Raw' storyline which caused WWE stock to plummet, and then happened as a sort of consolation of that despite being a terrible idea.
With almost every Raw now becoming a shill for whichever project or product the guest host was pimping that week it was painful to watch the vast majority of the time. "Highlights" include Jeremy Piven calling a SummerSlam 'SummerFest' and Dennis Miller absolutely tanking trying to use his political comedy during WWE's Slammy Awards. Crowds and audiences at home were treated to some lukewarm at best comedy and horrible acting almost universally. Even today when random celebrities show up it reminds us of this abomination and should be well steered clear of.
Honorable mentions to Seth Green and Hugh Jackman though.
3 Wasting Paul Heyman
Paul Heyman made SmackDown the true A-Show during one of Raw's worst periods when Triple H simply would not let himself be ousted from being front and center at all times. Given the on-air GM role and behind the scenes creative-control to freely make wrestling fun again, Paul Heyman actually toppled Raw as the premier show. But it couldn't last long with Vince and Stephanie resenting that success out of jealous pride.
Paul gave wrestling fans the SmackDown Six, Brock Lesnar's Ascension, great cruiserweight action and perhaps the hottest tag team division in company history outside of the TLC trio. When he butted heads with Stephanie behind the scenes he was sidelined to OVW developmental where he excelled again before being brought back to be on-air General Manager of ECW. During this time he had some creative control but was much more constrained, resulting in the disastrous December To Dismember, which was about the final straw.
Heyman could have propelled WWE to creative places they needed to go, but Vince's hubris and Stephanie's insecurity of being outperformed led them to ignore perhaps their best asset from either ECW and WCW.
2 Ignoring The Fans
One of the biggest lies WWE fans have to get used to as they watch Raw each week is that they have a true influence and voice on what goes on with their favourite superstars. Every year or so Vince will come out and say something along the lines of 'The WWE Universe is our greatest resource' but in reality Vince's mind is set in stone months before we get to see whether we like what he's serving up or not. Only when forced during the Attitude Era did Vince ever truly allow organic superstar growth for the likes of Steve Austin, The Rock and others, but that's no longer the case.
Always the biggest example of this is Zack Ryder, who created his own buzz and popularity with his web series 'Z! True Long Island Story' (which is still funny and relavent now considering his continued misuse) and had arenas around the country calling for him. Vince 'listened' insofar as he used Zack to further John Cena's storyline and then buried him forever. Another example is CM Punk and Daniel Bryan both struggling against the tide behind the scenes as well as onscreen, Vince ultimately getting what he wants both times even as we got a sliver of what we dared hope for. It was all Cena, all the time, and now it's Rawman Reigns for the foreseeable future, regardless of us.
In essence, the balancing act between giving fans what they want and delivering surprises they will love is delicate, but Vince veers far more towards his personal goals than the fans desires.
1 The Invasion
Could it have been anything else?
The Invasion remains the greatest missed opportunity for a massive storyline that WWE could ever have produced. They not only made it bigger than anyone could hope for by adding ECW and combining real-life events with the current storylines, but they made it worse than ever by absolutely dropping the ball in every way imaginable.
The reasons are all throughout earlier entries on this list. The burying of WCW, not waiting for the major signings that would've made it work, having their own talent usurp the leading spots for The Alliance, having the McMahon children as the leaders of WCW/ECW, etc, etc...
This storyline so badly damaged the WCW brand that WWE didn't even bother trying a resurrection as they eventually did with ECW. Outside of Rob Van Dam and Booker T, almost everyone from both rival companies was made the butt of jokes or a stepping stone for WWE talent and even those two got buried by Triple H after the fact to ensure the hierarchy was clear.
In short, the worst thing after the Monday Night Wars was the first thing. And Maybe Katie Vick too.