this is actually a very interesting question: when did they jump the shark? to me, jumping the shark has to be an occurrence that is outstandingly bad, it has to really stand out. there are so many options. i would go with wade refusing to wear headlines because it was completely senseless, but that seems way too early in the drought timeline. all the saint doug stuff seems way too late. and, given the team's history, rex's boorishness and general stupidity doesn't even qualify.
personally, i think they jumped the shark in the buddy nix years because he was so completely clueless and seemed proud of the fact that he wasn't particularly smart. it was either when he said his plan for free agency was to go to bed or when he was dumb enough to get recorded talking free agency with that tampa bay gm. i'm sure something equally deserving happened during the tom donohoe years, but i can't recall it right now.