He might be the Chairman of the company, but Vince McMahon is never shy about getting stuck into various storylines when needed. As one of the greatest characters in WWE history, Vince always seems to bring the best out of others in the ring. While he's obviously not the greatest wrestler in the world, Vince always knew how to take a beating to help others look great. Of course, with promos, there are very few better and because of that, he had some epic rivalries.
As with any WWE character though, some of Vince's rivalries did end up falling flat and becoming incredibly forgettable. So, within this list, we will rank Vince's five greatest and five worst rivalries.
10 Worst: Donald Trump
Obviously, now that Donald Trump is an incredibly controversial political figure, a lot of people look back at this rivalry with a different mood. However, even at that time, Trump was a very divisive figure.
That is one of the main reasons why the storyline just didn't work. Trump was actually the billionaire babyface in this angle with Bobby Lashley by his side. While it worked in making Lashley look like a top star, that's about all it did. Once again, Vince put himself to the next level by having his head shaved, but that didn't make this storyline a good one.
9 Best: D-Generation X
While many of Vince McMahon's biggest feuds end up being very serious, his rivalry with DX was the total opposite of that. It allowed Vince to show his funnier side and while there were still some serious moments, it was a lot more light-hearted.
Of course, that was always the nature of DX, with the tag team always playing different pranks and jokes on the boss. While sometimes they walked a fine line of being over the top, for the most part, they were very funny. Triple H and Shawn Michaels have a great relationship with Vince being great in real life, they were able to push him further than most. Because of that, they created some magic inside the ring.
8 Worst: Kofi Kingston
You can certainly make a case for this actually being a good rivalry, mainly because it got Kofi Kingston over in a massive way. Vince McMahon's refusal to put Kofi in the main event scene during the build to WrestleMania 35 was genius. It painted Kofi as the ultimate underdog and that is why it totally worked when it came to 'Mania that year. However, this storyline trod a very fine line of racism at times, which many fans weren't overly comfortable with.
On top of that, Vince was claiming Kingston was a B+ player, all the while Daniel Bryan was WWE Champion. Bryan, a man he had made those claims against for years, which just made his argument a little pointless.
7 Best: Shane McMahon/Linda McMahon
Vince McMahon has feuded with different members of his family at so many different times it's easy to lose track. But one of the best came around the end of the Monday Night Wars as it was revealed Vince had an affair.
This led to him starting a feud against his son and his wife, which eventually spawned the Alliance as well. It was an epic storyline that the family clearly put everything in to make a success. Fans will always remember the moment that a sedated Linda McMahon stood up to kick Vince in the balls. An epic moment that really summed up this crazy feud.
6 Worst: Roman Reigns
Whenever a WWE Superstar starts getting to new heights of stardom, it seems like Vince McMahon always ends up getting involved. He does so in the attempt to get a wrestler over to the next level and that's what he tried with Roman Reigns. The Big Dog was proving to be hit or miss with the WWE Universe, and in stepped McMahon and The Authority. Unfortunately, this time that plan totally backfired for Vince McMahon.
Fans were already sick of having Reigns pushed down their throats and this only intensified that feeling. Fans didn't want Roman in the main event and they certainly didn't want him feuding with Vince and the McMahon family.
5 Best: Eric Bischoff
Unlike everyone else on this list, Eric Bischoff was Vince McMahon's legitimate, real-life rival. The two men went head to head during the Monday Night Wars and really did have no love for one another. It created an amazing time for wrestling with fans not being sure what was going to happen between them. They would constantly call each other out during promos and interviews and push each other to do better.
Of course, in the end, it was Vince who came out on top and they eventually began to work together in WWE. This was a moment nobody ever saw coming, but it did provide some fantastic storylines on Raw.
4 Worst: Bret Hart
The epic rivalry between Bret Hart and Vince McMahon is something very real. The Montreal Screwjob is one of the most infamous moments in WWE history and it created a legitimate hatred between them. However, when peace was made and the Hitman returned to WWE to bury the hatchet with Shawn Michaels, they made it into a television story. Having Vince and Bret go at it once more wasn't something anyone wanted.
10 years earlier it could have been something magical, but this was too late. Both Vince and Bret were way past their primes and their WrestleMania match is one of the worst in the history of the event.
3 Best: CM Punk
No matter what Vince's personal feelings towards CM Punk might have been, he clearly knew he had a star on his hands. Because of that, he threw himself into a storyline with Punk that really did blur the lines with reality. With backstage contract issues being brought out to play in the middle of the ring, Vince and Punk would engage in some amazing promo battles. Even though they never ended up having a match with Triple H being the man who stepped up to try and compete.
The storyline certainly helped Punk during the peak of his WWE career, helping to put him over in the biggest way possible. Even though Punk has his complaints about the company, he can't deny that Vince tried to get him over as much as possible.
2 Worst: Hornswoggle
What a complete and utter mess this situation was. After months of build p regarding Vince McMahon's illegitimate child, a storyline that had tons of heel potential, WWE just gave it up for a comedy storyline by claiming it was Hornswoggle.
Obviously, this was meant to be Mr. Kennedy but other issues forced a change to take place, but surely WWE could have thought of a better choice than this. It simply made no sense and fans didn't care for it. In the end, the whole thing boiled down to a storyline between JBL and Finlay, which just about summed up the entire mess that this rivalry was.
1 Best: Stone Cold Steve Austin
There was only ever going to be one person topping this list. The rivalry between Stone Cold Steve Austin and Vince McMahon isn't just the best of Vince's career, but it's one of the best in WWE history.
This was one of the focal points of the Attitude Era and helped change the tide of momentum in the Monday Night Wars. With Austin sticking it to his boss being something that everyone could relate to. Vince would do everything in his power to get in Austin's way and screw him out of success. But, of course, Austin would always come out on top with a stunner and a few beers to celebrate.