Biggest Lost Opportunity

Bigger lost opportunity in terms of matches and feuds that could or almost occurred?

Savage 92-96 (w/ Michaels, Razor, Bret, Owen, healthy Nash)

Michaels 98-02 (w/Rock, Austin, pre-leg injury HHH, Foley)

Lesnar 04-08 (w/ Edge, Batista, Cena, Jericho)

Yeah, Savage would have been GREAT working with the up and coming crew of new guys, especially Shawn and Owen. And as noted, Diesel v. Savage could have carried a couple of PPV shows. And how about Savage v. Undertaker at Wrestlemania? So many wasted opportunities there.

With Michaels in the Attitude Era, I feel like he got out at exactly the right time. After the Austin feud he probably would have been increasingly marginalized by Russo and made into another guy, whereas going out like he did turned him into a legend and allowed him to come back after the style had changed away from the crazy brawls that ended his career in the first place.

Brock also I think was in danger of becoming 50/50’d to death had he stuck around. Doing a job to Eddie was a bad sign in itself, but the stuff with Big Show in 2003 and trading wins with Kurt Angle was just killing him as a character. Leaving was the best thing that ever happened to his character.

So yes, Savage wins this one by far, I think.