He got title shots because he was a credible threat who had good matches in that kind of environment.
He wouldn't have got the title then, but I think there's a bit of...I don't want to say jealousy, but regret, perhaps... for those of us who were big fans of upper mid card guys in the 80s and 90s, looking back at how many folk got title reigns since the first brand split that would have struggled to see the IC title back then. In a world where Miz, Ziggler and Swagger all won the World title, the likes of Bulldog, Owen, Bossman, and my main man Perfect would have pissed world titles in their sleep had there been that set up back then.
Compared to today's league every single mid-carder from late 80s to 90s could have been a more credible champion. Bam Bam? Absolutely! Perfect? Please lets not even argue about it. Rude? Snake? DiBiase? Razor? Even Tito and Martel could have filled the shoes back in their hay day. Today someone like Bulldog would be an obvious choice for a championship material. Vince would trade Roman for Bulldog in a heartbeat.
Bulldog is always a weird one to me, a great wrestler who seemed to float between World title and IC title shots. I always liked him. I think he could play off the snobby British gimmick well if paired with William Regal perhaps. I could see him as champ for a while I guess. I think he had the look and the ability to make it work for a while. His promo skills were never amazing, but they were adequate. In 1995/1996 I accepted Bulldog as a legitimate contender. It was weird to see him lose so decisively against Shawn in 1997. I don't know why it never really worked out for him when he returned in 1999, he looked in good shape but I guess he wasn't so well.
I don't understand why Bret never had an issue with eric firing Bulldog when he hurt his back on Warriors trapdoor.
Nothing interesting here my friend. Look further down.
For 1995-1996, his title shots probably came because of how thin the roster was. Another reason I see, as someone mentioned, because of the heel turn. Bulldog was a Ricky Steamboat or Tito Santana type who ALWAYS was a good guy. The shock value of him turning (and on the HW champ) had to catapult him to main event.
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I never especially thought Bulldog was an effective heel. He just never said or did much that was all that evil. His whole turn on Diesel was weird because it's not like he had any connection to the guy in storyline. Just a random turn in a tag match. Even the maligned HBK feud didn't really make him seem all that evil, just a guy defending his wife's honor (was he even in on the Diana lies?). Even in the Bret bloodbath match he never especially targeted the cut and when Hebner went down he actually helped the ref up, haha.
I'm not even sure what I'd call him in 1997. He veered toward a face turn in Feb./March 1997, but then joined the Hart Foundation. But even then I'd say when they went to Europe or Canada he was a total face, despite being nominally a heel in America.