Davey's best shot at the title of the 3 would have been the first one against Diesel. At the time he had just turned heel and was the best heel the company had at the time as Yoko was at the very end of being relevant and Mable was a flash in the pan in 95. WWE was still invested in face Diesel at the time so Davey missed his chance there. This would be his best shot as by the end of 95 Bret got the title to set up the Mania 12 match against Michaels. by the end of 95 Shawn was positioned to be the top face and Bulldog was not the guy to begin that title reign against. So there was really no shot for him to beat Bret. Then his last shot against Shawn was early on in Shawn's reign and not only was there a lot invested in him, but they needed to establish Shawn as the huge face with Bret gone and Taker using 96 to get himself to that point in 97.
As some have mentioned here the absolute best time for Bulldog to have had a title reign would have come in 93 had he not gotten fired. It would have made too much sense once Bret got the title in the Fall of 92 to have him in a program with Bulldog at some point after their program that culminated in the classic we got at Wembly. If Bulldog is still around maybe the company doesn't go as hard as fast as they did with Yoko which could have positioned Bulldog for a run with the title at some point in 93.
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