As sure as water is wet and the sky is blue, Vince McMahon being the eccentric billionaire he is, is guaranteed to upset a few people on a daily basis. As a businessman, an icon and a revered boss, Vince McMahon truly is the epitome of a ruthless tycoon. The man solely responsible for the biggest sports entertainment company in the world has an unbearable burden like no other. He orchestrates star promotions night after night to sustain his livelihood. It's through this dependence that unique relationships are formed. He needs his top guys to deliver in order for him to make money, so the question remains, if he needs them and cares for them, why do so many conflicts arise?

Vince's ruthless attitude towards business is something he translates into his approaches with people, so, even though he depends on his stars, in his twisted mind, they would forever be indebted to him. This mindset created friction because Vince created these stars and then these stars began to believe they were who Vince said they were and it all went downhill from there. Egos constantly arose and tempers began to flare as the newly created stars dared to challenge Vince instead of continuously bowing down to him. His arguments with his top stars became so common and regular that it was almost like a rite of passage to stardom.

Here are 15 separate occasions in which the chairman of the board went face-to-face with his most prized assets.

15 15. KURT ANGLE - Schedule

If you don't know by now, Vince is an egotistical maniac that prides himself on being physically and financially superior to all those around him. He was often known to physically dominate his employees to the point where they would admit he was the tougher man. Kurt Angle and Vince often engaged in jovial grappling sessions wherever they saw fit.

However, their fun-loving relationship would turn sour when Kurt told Vince he was no longer able to work a full-time schedule. Vince took this to heart and responded with rage, accusing the Olympic gold medalist of selling out. After Vince calmed down, the two settled on an agreement for Kurt to rest for a while and then come back to work when he was ready. Instead, Angle became a free agent and joined TNA. Vince was hurt and out of spite, he's never fully entertained the idea of a Kurt Angle return since.

14 14. TRIPLE H - Breaking Kayfabe

Perhaps their close ties gave Hunter a false sense of security in thinking he could stand up to the boss like no one else, but when you work for Vince, you're an employee, nothing more, nothing less. History has revealed to us that Hunter has always been one to rebel against authority. Who could ever forget that time in The Garden in 1996 when he and his fellow Kliq members broke kayfabe and as heels & faces held hands together to the admiration of the crowd? This sent Hunter to the doghouse and his career looked to be over before it had even started. Still, we all know how the story played out from there; eventually, through relations with the boss's daughter, Hunter became a powerful presence backstage.

But if you thought that'd stop the rebellion, you thought wrong. It only inflamed it. Now we can't go a few weeks without hearing about the butting of heads between the two over the creative direction of the WWE.

13 13. RANDY ORTON - Wellness Violations

It's no locker room secret that the exceptionally gifted youngster was an absolute pain to deal with backstage. His immature attitude and entitled personality rubbed a lot of co-workers up the wrong way. You only have to look at his suspension record to gauge an understanding of how difficult he was. With three suspensions and two wellness violations to his name, it's fair to say if it wasn't for his exceptional in-ring ability, Vince would have disposed of him ages ago.

His constant meddling with marijuana led to several backstage showdowns with Vince, who often questioned his commitment to the business. Thankfully under the mentorship of Triple H, Orton began to mature as a man and as a performer in the ring. Today, he is now one of Vince's most trusted main event talents and has won the respect of all his peers, but things could have easily been different for Randy if he wasn't so damn talented.

12 12. SHAWN MICHAELS - Creative Differences

Didn't think you'd see this name on here, did you? It's a well-known fact that Shawn Michaels was Vince's prized possession, the apple of his eye back in the 90s. Shawn could literally do no wrong, according to many in the WWE. Vince's love stretched so deep that when Shawn was out injured with a back injury, rumor has it the Heartbreak Kid was still bing paid a million-dollar contract, collecting regular monthly payments. Shawn was spoiled and entitled because Vince seemingly allowed him to be during his run as the WWE Champion. Before becoming injured it's a well known fact that HBK and Vince would get into verbal altercations due to creative differences, with Michaels refusing to do jobs for guys he didn't think deserved them; specifically Bret Hart.

When Shawn returned in 2002 on a more part-time basis, McMahon reportedly threw jabs at the former champion, something that didn't set well with Michaels.  Backstage officials claimed the two began to have a more frosty relationship during this time period, which would often lead to several awkward arguments in which neither really had a leg to stand on. In any event though, their relationship seems to be as strong as ever today. Probably like that of a father and a rebellious son.

11 11. CHRIS JERICHO - Jericho being Jericho

The ayatollah of rock 'n' roller thought of himself as quite a big deal when he first arrived in the WWE on that memorable day in August of 1999. There were high hopes for Jericho from the fans and Vince. However, when it was apparent the Canadian-born wrestler wasn't living up to the chairman's high standards, Vince let him know in no uncertain terms. Jericho's fiery character wouldn't allow him to humbly accept the criticism, and news of the dispute would spread around the locker room like wildfire.

Eventually, Vince put his faith behind Jericho, with the WCW becoming the first WWE Undisputed Champion. Truthfully, these two have had several blow-ups since Jericho became a main event talent. These incidents include arguing over a suspension for kicking a Brazilian flag, and a huge fine for blading during the PG Era.

10 10. MICK FOLEY - Commentary

How you could ever have an argument with Mick Foley, I'll never know, but Vince managed it somehow. Foley was a performer that had a knack for the getting best out of any gimmick he was given. He truly loved the business and the art of wrestling. After a seasoned career in the ring, the three-time WWE Champion decided to try his hand at the commentary table. Unfortunately, I'm not sure Foley knew how restricted his creative freedom on the mic would be. As we've heard through leaked SmackDown audio recordings, Vince basically feeds his announcers lines to spew live on air. If they dare to not repeat his lines word for word, they'd receiving a bollocking through their headsets. This didn't sit well with Foley and he verbally confronted the 67-year-old backstage on numerous occasions. After a while, the stress began to outweigh the enjoyment for Mick and he packed his bags and hopped over to TNA.

9 9. KEVIN NASH - Lying to Vince

Big Daddy Cool aka Diesel aka whatever else you want to call him, was notoriously a difficult talent to manage. Rumors made the rounds about Nash politicking backstage until the planned outcome of a match changed. Nash's membership in the Kliq, and his antics behind the scenes would create an unsettling atmosphere backstage for all parties. And when Scott Hall made the daring switch to WCW, Nash would politely follow suit despiting promising Vince that he wouldn't make the jump.

Vince was livid, and rumor has it that he let Nash know it after finding out. Not only was his pride at stake but his whole entire livelihood was too. This conflict would better be described as a silent one, as Nash and McMahon's relationship was severely strained as a result of this act of treason.

8 8. SCOTT HALL - Leaving For WCW

The original bad guy, the man who made it cool to cheer heels, Scott Hall/Razor Ramon provided a unique sense of pizzazz to the wrestling industry. He embodied what Vince wanted his industry to turn into, a mix of athletic ability and showmanship. But it’s when Hall started to realize his worth, that things turned sour. Scott Hall has been reported as having many disputes with McMahon over his pay and merchandise royalty. He cited particular conversations that he had with the chairman, where Vince wouldn't budge on compensation.

After differences over contract demands, Hall decided to leave the WWE for greener pastures and Mr. McMahon just couldn’t accept it. Hall’s switch to WCW showed the rest of the locker room that there was a life after WWE and that WCW was a viable financial alternative. Vince also took offense in the former IC Champ’s ability to persuade Kevin Nash to join him on the other side. For the following few years, Vince would hold a grudge, and he would refuse to mail Hall any of his royalties, despite sending Nash his. The switch had seriously hurt the chairman and he reacted with no class or decorum.

7 7. STONE COLD - Jobbing to Lesnar

Even the Texas Rattlesnake couldn't stand Vince's antics at times. Although the two pillars of the Attitude Era were entertaining foes on air, it's no secret that the two had great respect and admiration for each other behind the scenes. They made each other a heck of a lot of money and perhaps that is what cemented their respect for each other. However, as with everything, Vince is strictly about business regardless of your status in the company.

In 2002, it was evident to everyone that Austin's time at the top was coming to an end, as he had put on weight and constantly complained about having joint pains. Vince sensed the end of Austin's time as a top guy and decided it was time for the Rattlesnake to put over Lesnar on during a King of the Ring qualifier on an episode of RAW. Austin strongly disagreed, and the had a civil conversation over the phone, but The Rattlesnake didn't show up to the event. He walked out on WWE and didn't return for nine months.

Jim Ross would eventually set up a sit-down meeting between the two men in a hotel room, which Austin described as heated but beneficial.

6 6. CM PUNK - Broken Promises

Sometimes people go into the business with a genuine love of it and end up getting worn out by the politics that run it. Punk's comments after his controversial exit from the WWE portrayed the frustration of another top guy tired of Vince's nonsense. He told the story of how petty the boss was to him, and how the company officially sacked him on his wedding day. He went on to say how Vince failed to deliver on several promises and how the WWE refused to permit him certain mainstream opportunities while permitting other wrestlers the same thing. Before leaving the company however, Punk, Triple H and McMahon engaged in a closed-door meeting that by all accounts got pretty intense.

Punk hated Vince's way of running the business and Vince seemingly despised his resistance. In a rare series of events, Vince actually publicly offered an apology to Punk on Stone Cold's podcast, to no effect. Punk's refusal to forget the promises made to him rubbed Vince up the wrong way. A big role in Punk's disgruntlement was a disagreement they had over pay from WrestleMania XXIX. He then walked out in January 2014 after finding out he wouldn't be main eventing WrestleMania XXX.

5 5. HULK HOGAN - Bigger Than Wrestling

This list just wouldn't feel right without the Hulkster's presence. Despite arguably being the biggest star in wrestling history, Hogan wasn't exempt from the wrath of Vince McMahon. The bad blood seemed to stem from Hogan getting a little too big for his boots. Hogan had developed an untouchable attitude, often booking his own matches and refusing to put others over during the height of his career in WWE. The fame had gotten to his head and the bright lights of Hollywood had come calling. After an argument over work dates, Hogan would commit the ultimate act of betrayal by jumping ship to legitimize the threat of WCW.

The jump to WCW hurt Vince so bad that the two weren't able to reconcile in the same century. Hogan would make his heroic return in 2002 but rumors suggest that there was always noticeable tension between the two. This wasn't helped by Hogan refusing to job to Michaels in 2005, thus continuing his egotistical actions from the 90s. Despite being the superstar that generated Vince his most amount of money, he sure did provide him with an equal amount of grief.

4 4. BROCK LESNAR - Done With Wrestling

This was one of the few times in history that Vince literally put all his eggs in one basket. Never in history had a young wrestler been pushed the way Brock Lesnar was in the early 2000s. Just look at who he beat in his first run in the WWE; Hogan, Undertaker, The Rock & Kurt Angle all within the space of two years. Vince made him HIS star, and never in his wildest dreams did he think the former NCAA Champion would turn his back on the company. But as with most mega-stars, the top is never enough.

In 2004, Lesnar let Vince know that he wasn't cut out for the road life, and wanted to leave the WWE. He didn't care about what Vince had done for him, he just wanted to leave. Vince threw all the money he could at the youngster but he refused to listen. The two would then have numerous heated discussions backstage in the lead up the WrestleMania XX. Lesnar was forced to put Goldberg over in one of the worst WrestleMania matches in history. The Minnesota-born wrestler would gracefully exit the WWE by flipping the bird at the MSG crowd before receiving a stunner from Stone Cold.

3 3. BRUNO SAMMARTINO - Changing the Product

This entry is for Bruno Sammartino, the man who made Madison Square Garden his second home. For those who don't know, Bruno was insanely popular back in the 70s & 80s. Night after night he would sell out The Garden and solely carry the WWE on his back. However, after Vince McMahon Jr. took sole control of the company, things started to change. The focus began to shift away from wrestling and went towards a more entertainment based product. Sammartino despised this change and had some well-publicized disputes with the chairman himself. He didn't feel comfortable with the change in his surroundings and went on to retire from in-ring activity in 1986. After a few years on the commentary table, Bruno couldn't take it anymore and made a big deal out of leaving the company.

The legend even went on television to publicly criticize Vince and the ever-evolving wrestling industry. Bruno is one of the biggest stars ever and it was only through the mediating of Triple H that the former WWE Champion was able to reconcile with the WWE, subsequently accepting the Hall of Fame induction in 2013. The Hall of Fame could never have been complete without the presence of Bruno Sammartino.

2 2. THE ULTIMATE WARRIOR - Money Issues

Yup, this wasn't a surprise, was it? It's very well documented that after his time with the company, the Ultimate Warrior spent most of his days with hate in his heart towards Vince McMahon & Hulk Hogan. The bad blood apparently stemmed from a financial demand made by Warrior back in 1991. Vince didn't take too kindly to the wrestler asking for more money and subsequently relieved him of his duties the following year. Bygones would become bygones and the Warrior would return at WrestleMania VIII, but controversy would follow as he was fired again, this time for an incident involving drugs.

Vince who's always been willing to put personal reasons aside to make money would again bring back Warrior in 1996, but it was clear his wounds had not healed. The two refused to reach each other's expectations and the relationship soured again. Warrior began to act recklessly backstage and Vince made it a hat-trick of sackings for the now Hall of Famer.

1 1. BRET HART - The Screwjob

As competition heated up between the WWE and WCW, the status of top stars on both brands began to come under scrutiny. Bret Hart and Shawn Michaels were undoubtedly the two top stars for Vince and with Shawn's unquestionable love for the boss, it left Bret as the only one that WCW could snatch away... and snatch him they did. When Vince conceded defeat in not being able to pay Bret's 20-year contract, WCW came calling with a huge contract. Bret was the WWE Champion at the time and would inevitably have to drop the title before he left. This is where the dispute began.

Survivor Series was coming up in Bret's home country and he was 100% set on not dropping the title in Canada to Shawn Michaels. Vince felt he couldn't take the risk of Bret walking away with the title, so he took matters into his own hands. And what followed, was probably the most memorable moment in WWE history. Bret was screwed, scarred and embarrassed for life. A meteoric argument would take place between Vince and The Hitman backstage, an argument which led to Bret socking Vince in the jaw. It would take almost a decade of time to heal this wound, and to this day some would say Bret has forgiven, but not forgotten.