Diamond Dallas Page is regarded as one of the finest WCW legends in history. Even though he started his wrestling career late in his 30s, DDP went on to achieve a ton of success in the wrestling business.
After the death of WCW, Vince McMahon brought many ex-WCW talents to WWE and buried nearly all of them in The Invasion storyline. Diamond Dallas Page also joined WWE in 2001 but as The Undertaker's ex-wife Sara's stalker. This would lead to one of the most baffling debuts for a wrestler ever.
The Unluckiest WCW Wrestler In WWE History
Page started his wrestling career as a manager, but then became a wrestler as well. His rise in WCW was very organic as he transitioned from a lower mid-card heel into a popular babyface character.
DDP also has three WCW World Title reigns in his name. He defeated Ric Flair, Sting, and Hulk Hogan in the same night to win the crown. In a perfect world, this would've been a huge deal (and it was) but WCW didn't capitalize on the opportunity properly.
By the time DDP won his first World Title in WCW, the company had started to become a mess. Shortly after winning the title, DDP lost it to Sting in an episode of Nitro and regained it the same night in a fatal four-way match. His second reign ended in less than two weeks, whereas his third and final one only lasted for a day.
Page's WCW career wasn't perfect at all, but he was still one of their homegrown talents that the fans really loved. Even in WCW's dying days, Page was a huge superstar. But it didn't take long for WWE to ruin him.
As part of The Invasion storyline, Page finally made his WWE debut in June 2001 after several weeks of build-up. He revealed himself as the stalker of Undertaker's wife, Sara. DDP wanted to get the attention of The Phenom and he was successful. However, there was no way he was winning in this storyline; the Invasion storyline was seemingly designed to bury WCW, and Page was feuding with one of WWE's greatest characters of all time. The feud with 'Taker ended up eliminating all possibilities of having a successful career here for DDP.
At King of the Ring, he and Undertaker brawled each other in an unofficial match. Some timer later at SummerSlam, The Brothers of Destruction teamed up to defeat DDP and Kanyon inside a steel cage for the WWF Tag Team Titles. The next night on Raw, Sara herself pinned Page in the middle of the ring (with Undertaker's assist, of course). This ensured that fans would never look at DDP again the same way.
DDP took some time off to recover from an injury that he suffered at SummerSlam and returned with a new gimmick. This time, he was a motivational speaker who exuded positivity (maybe he could have joined the New Day if they were around). But the damage had already been done, and there was no simple way to fix it. After a few wins here and there, including a reign with the WWE European Championship, DDP retired from wrestling after a botched superplex from Hardcore Holly.
DDP Regrets Agreeing To The Storyline
Page said that he initially hated the idea when WWE pitched it to him. Bruce Prichard was the one who came up with the storyline and he thought it was a great idea. In an interview with GiveMeSport, the company originally wanted "Stone Cold" Steve Austin to be the stalker but he immediately rejected the idea.
Nobody else was agreeing to do it, and then Vince McMahon asked DDP to play that role. Even though Page didn't like it, he went ahead with the idea and played his part. And that ended up being one of his biggest regrets in wrestling.
There were also rumors that The Undertaker didn't like DDP and wanted to bury him with the whole thing, both Page himself clarified that he and The Deadman are good friends and never had any sort of heat with each other.
DDP Wanted The People's Champion Vs The People's Champion
Diamond Dallas Page was also known as The People's Champion. The only other superstar to be famous by this nickname was The Rock. DDP wanted to debut against The Rock in WWE but his pitch was rejected by the company.
Even though DDP's WWE career wasn't so great, he did achieve greater success outside the wrestling business with his fitness program. DDP Yoga saved many people with this program, including WWE Hall of Famer Jake Roberts (also his mentor) and Scott Hall.