I hope this is a good question.

WCW's main event roster at this time was STACKED -- but often underdelivered

DDP was a fantastic performer who had a super fresh and unique style

In a lot of ways, he became a "work horse" type of guy that you'd put in the ring with anyone. They trusted him in a huge PPV main event with Goldberg, and he was main eventing PPVs against Randy Savage without a championship in the mix. WCW was positive about that he could get a match out of Karl Malone and Rodman. He seemed to be "the guy" that WCW pointed to when they just needed to deliver in the ring on something

That magic would have been lost in the WWF in my opinion. WWF's main event scene wasn't stacked like WCW's but the top guys they had were on fire. I don't know if DDP would've gotten those giant pops if he is coming out on the same nights as Austin, DX, the Rock, etc.

DDP's run in a lot of ways was just 'right place, right time' to me. No doubt his talent would've broken through on some level but I think DDP wouldn't be looked at nearly as fondly if he was a RAW IS WAR guy.

I think his role in the Invasion in some ways might support that claim. His character without a doubt was horrible but a bad gimmick on a good wrestler has worked in the past. The WWF crowd just did not care when DDP showed up. For the most part, he went back to being normal DDP in early 2002 but even then, he just wasn't really over with the audience for some reason. It could be 100% the poor creative but he just wasn't a guy who worked well in WWF. 

Limited knowledge on DDP but could see him being a good hand to throw in to the main event mix.to create fresh match ups, similar to Benoit’s role early 2000’s.

There were a few ex WCW guys kicking about (Austin, Foley), so he would have had a few friends. And as much as Shawn was acting up, 97/98 didn’t seem as much of a political snake pit as 2001 onwards.

Around that time as well Vince seemed more eager for anything to catch to compete with WCW, so probably would have been his best chance for Vince letting the true DDP character shine through. But as mentioned by others, he would Have been at the mercy of Vince’s whims - anything from World Champion to the proud father of a hand.

Not too familiar with DDP's WCW run as I know him more from his WWE stint, acting in movies and his Yoga program but I think the guy had the look, the walk and clearly has the gift of gab on top of it all. With people like Rikishi, Jarrett, Bossman, D-Lo Brown, Test, Al Snow and even Val Venis all getting solid reactions during that era, I feel like DDP would've been able to find his stride relatively easily. I'm not saying he would be the next Rock or Stone Cold. Probably not even the next Angle or Eddie but I don't think he would have sank at all. Anybody who could deliver on the mic in that era was getting tv time and DDP can deliver on the mic.

Maybe it wasn't always that way but again, I only know of him what I've seen post wrestling and his short stint in WWE where they gave him the stalker gimmick off the bat up until The Invasion arc that could have been so much better had Vince not felt the need to flex his nuts on the talent coming over from his competition. Instead of having 13-15 main event players between the WCW signees and the ones already in the WWF, they buried countless talent to make 6-7 homegrown talent look better. That's a decision I will never understand. All he had to do was treat them properly as people who were making ends meet in another promotion and the bigger names like Flair, Hogan, Goldberg, Big Poppa Pump, Sting, Outsiders, Perfect/Hennig and Mysterio (even as an invader he could have been cheered like RVD) most likely would have been open to having contract talks. I loved the angle and all the things we got from it as fans of a blessed era of wrestling but what could have been is still so much more. Sorry for the rant.

Picture Vince trying to recruit em to the Corporation with him looking like he'll join only to Diamond Cutter em ala what he did to Scott Hall

Just imagine the POP

all it would’ve taken is him hopping the barricade and hitting the diamond cutter on someone who matters and he would’ve been one of the most over guys on the planet

I think he would have gotten over with the fans, but like Joker said he would have been lost in the shuffle.