Obviously the titles have become devalued in WWE, but what do you think was the worst year in terms of damaging the world title?
I think Russo's 1999 wins by a landslide. At that point, the title still at least meant something, but the spastic booking of the title that year was ridiculous. We had Rock becoming a THREE-time champ between Survivor Series 1998 and the run-up to Wrestlemania XV. Austin wins the belt, but drops it to Undertaker who wasn't even the #3 guy in the company at that point. Austin gets it back, but drops it in a weird three-way to Mankind…who jobs it to HHH the next night. HHH's push hits a speedbump when he drops the belt to VINCE MCMAHON…who vacates it, only to have HHH win it back in the six-pack match. Hunter finally beats Austin (which should have happened at SummerSlam to give it any meaning in the first place), but drops the belt on-the-fly to Big Show…who defends in December against Big Boss Man? What a headache. It was so bad that I still remember it off the top of my head.
If we're considering other promotions too, then 1999 surely wins because WCW wasn't much better that year. Nash enters the year as champ after the ill-advised Goldberg job. He lays down for Hogan. We get sheisty booking of some Hogan-Flair matches. Flair gets the belt, but drops it the next month in a four-way…to DDP? They do the DDP-to-Sting-to-DDP title switches on Nitro. Nash takes it BACK from Page at the very next PPV. Instead of dropping the belt to Sid to set up the Vicious-Goldberg program, he drops it in a TAG match to….Randy Savage? Savage jobs the belt the very next night to Hogan (just like in 1998). Hogan faces Nash at Road Wild ANYWAY and retains. Sting takes the belt in one of the worst heel turns ever, drops it to Goldberg in an on-the-fly match that had no hype or build-up. He loses it to Bret Hart in a contrived Montreal knockoff, retires Bret for real, and the title gets vacated. An even bigger headache that parlayed into the Sid-Chris Benoit "title win" thing and ANOTHER vacancy.
I think 1999 takes it,but then I haven't actively watched the current product since about 2003, so there may be worse years.
99 WCW, and 2000 for that matter, were both HORRIBLE, but that might be just a subset of the general horribleness of the product at the time, hard to say. I do have to say the Russo/Bischoff Crisis on Infinite Earths reboot of the promotion and vacating all the titles did irreparable damage to the company in general, not to mention all the belts. Never mind that Booker T won his first title from Jarrett, the guy who wasn't even CHAMPION at the time. Having three vacancies (Benoit vacates, Sid vacates, Hogan vacates) and "starting a new era" deals within a couple of months of each other did way more damage to that belt than the rapid-fire Nash/Hogan/Flair/Savage switches did the year before, IMO.