DDP as a horseman in this fantasy booking works. Would have been a perfect fit at that time. Dude had a finisher that people loved, and he worked well as heel or face, but he doesn't get Arn's spot in my booking.
Bret comes into WCW late 97, and immediately looks like a tool because of how the ref pissed all over the ending of Sting/Hogan at Starrcade. For my booking to work, this match doesn't happen. See later in the post for why. Instead, Bret comes in fresh off being screwed in Montreal, and is sick and tied of the company up north, and won't stand by a couple of it's rejects doing the same screw jobs to guys in WCW. He joins the horsemen, and for a while the horsemen are Flair, DDP, Benoit, and Bret. For the better part of the next year, you can mix and match battles against the NWO, put Bret and Benoit as a tag team to Hall and Nash, but the NWO gets the better of them throughout this feud.
Now, what should have happened with Sting. Send Sting on a long vacation and have him nowhere near a WCW event after his telling his doubters to stick it. Send him to Japan for the year and a half if he wants to stay in the ring, but keep him out of the US. No crow gimmick, no broody, silent dude in the rafters. None of it. No fake Sting in the nWo. Legit send him away. (As a side note, Bret is happy without even knowing it, because not sending Sting to the rafters means Owen doesn't die.)
In the month before Fall Brawl 98, set up a war games match, Hogan, Hall, Nash, and Macho against the Horsemen. The stipulation, the loser of the match has to disband their stable. Two weeks before the PPV, Hall and Nash storyline injures Benoit, sending him home for a few months and out of the War Games match.
On the Nitro before Fall Brawl, have the NWO say if they can't find a guy, they gotta do the match a man down. Do a couple backstage segments of Flair on the phone trying to get "his guy", but leave Nitro thinking they are still down a man.
The night of the PPV, have the announce team sell that only three horsemen have been seen in the building, Schiavone was great at selling WCW at it's darkest hour ish. Right before the match, have Flair, with just Bret and DDP cut normal crazy Flair promo, the horsemen against the world, woo about 59 times and start the match.
As always, heels win the toss, and it is a 1 man advantage for them the entire match for a horseman beating. Everyone the audience knows of is in the match, and the clock expires for the 4th man to enter. No one comes out, and as the NWO assumes there is no 4th guy, Sting comes out, not in crow gimmick, but black and white face paint like he wore before going all crow. NWO and the horsemen stop fighting as Sting walks in, and you get a three man staredown of Hogan and Flair in opposite corners with Sting in the middle. Sting Stinger Splashes Hogan and all hell breaks loose. Horsemen make the comeback and win, NWO disbands, and for a while, you got a horsemen faction of Flair, DDP, Bret, and Sting.